Dating can be awkward enough as it is, but it shouldn’t have to be this hard. From crazy cat ladies to momma’s boys and everything in between, these people have seen it all. Sure, maybe these dates didn’t lead to true love, but at least they led to some absolutely insane stories!
1. The More You Know!
I met this girl and hit it off pretty well with her. I hang out at her place one night, get home, and decide to look her up and add her on Facebook. As soon as I look her up, I discover that she has an eight-month-old kid and a husband in Iraq. Both details she decided to leave out. When I confronted her about it, her response was unbelievable. She just said, “Well, I didn’t think that would bother you.”
2. Law and Order
I once went on a date with a law enforcement officer. My mom set it up but it seemed like he was an alright guy, so I agreed. We went out to lunch. He proceeded to tell me about his kids and talk about his hobbies. Afterward, he offered to show me around the town since I had just moved here. Turns out he was actually driving over to his ex-wife’s house to introduce me to his kids.
They seemed to not be home, so he went to the windows and peered inside to make sure. At this point, I just wanted to be out of there. When he got back in the car, I politely asked him to take me home. He did, and I told him I’d call him sometime that week. I never called him, and for about a month I was completely paranoid that I’d get pulled over by one of his buddies.
3. Pick a Partner
My prom date was pretty bad. It was a double date with some girl I’d never met. Turned out we had both just been dumped. I tried to make conversation about random topics, but she just wanted to talk about how annoying her ex was. We get to prom and it turns out that her ex, who I’d also never met, was there—but that’s not the worst part.
He was there as my ex’s date. My date then spent the rest of the evening trying to get her ex to come back to her.
4. Memory Loss
This is not the worst thing that ever happened, but it’s still kind of funny. I once took this girl out for a first date. We went to a play and then out for drinks at a bar afterward. While we were enjoying our drinks, she suddenly stopped me in the middle of our conversation and said: “You don’t remember, do you?” Turns out we had slept together like five years earlier…
5. Dinner and a Show
I would have to say that the worst date I ever went on was the one with the girl who came to my house to “make me dinner.” She showed up with a bottle, popcorn, and a movie. We consumed it, and she decided it would be fun to run around our neighborhood, screaming and doing cartwheels in the streets. I said sure. Out we went.
She climbed a tree. I climbed the tree after her. We slept together in the tree. What was so bad about this date, you ask? One of my annoying, silly sperms decided to go and fertilize one of her eggs. She had a miscarriage when she was about three months along. I was not looking forward to having a child with this crazy girl…
6. Twist Ending
I once went on a blind date with this girl. We started with a movie, and everything went okay throughout. The real disaster actually only happened as we left the theater. After the movie finished, as we were pulling out of the parking lot, she saw her father leaving the same movie…with a woman who definitely wasn’t her mother.
7. Stay Hydrated
It was my freshman year of college. He took me to Wendy’s for a date because neither of us had a lot of money. He had one of those monotone voices, and could drone on and on and on about nothing. He was telling one such story when I swallowed my water the wrong way and started coughing. This was still a date, so at first, I tried to politely expel the water, but to no avail.
As he continued to talk, I started hacking all over the table. Tears were streaming down my face, water was dribbling down my chin, and I was pounding my own back at a futile attempt to get the devil water out of my system. He kept talking. Trying to hold the water in at first was a bad idea. I could not stop coughing. But then it got so much worse.
I bent down under the table, hoping the angle would make it easier to cough up the liquid. Everybody in the whole restaurant was staring at me in silence. Except for my date, of course. He was still telling his story. I finally finished hacking up my lungs and tried to listen to the rest of his story. I had no idea what he was talking about.
He continued with his anecdote, unfazed by my wet, red face and smeared make-up. When he finally finished, I apologized for my coughing fit and explained that I had swallowed my water the wrong way. To which he replied, “Oh, I was wondering what was wrong with you.” Thanks, my dude. We did not have a second date.
8. Close Calls
I had a great date with a girl I met on a dating site and I was walking her home at the end of the night. All of a sudden, she started to run. I started to chase after her and when I caught up, I asked her what happened. She just said, “The fuzz! I have a warrant out for me.” I said forget this and left, but went in a different direction than she went—but the story didn’t there.
While I was walking home, the authorities pulled up and started asking questions because they’d seen me with her. I had to spend a good 20 minutes explaining the situation to them and how I was in no way involved in her criminal activity.
9. The Witch
I was sitting at a bar on a date, when out of nowhere my date informs me that she is a witch and that she had made her last boyfriend love her by casting a spell on him. She was even nice enough to tell me how the spell “worked.” She took a vial of her period blood and poured it into his drink, and tricked him into drinking it. As she said, “Now he’s mine forever.”
She went on to say that it turned out she didn’t really love him, but because of her spell, he would love her forever. She claimed he was still desperately in love with her even though she had dumped him. Yikes.
10. The Second Date
I got invited to a party as a second date. The girl met me at the door and walked me to where the band was playing, she then walked away with some guy. I didn’t see her for a good hour before I decided to leave. Turns out he had some “party favors” and she slept with him to score some. I guess he ended up being the one to do me a favor.
11. Paging Dr. Freud
I went out with a guy who talked about his mother literally the entire time. I knew her favorite foods, movies, where she went to college, how she makes her spaghetti sauce…you name it, I heard it. At one point I suggested he date his mom since no other person could compare to her. He looks at me almost like he’s contemplating it.
I look at him like he’s psychotic, and he yells at me and says that anyone who is half the woman his mother is should get down on their knees and thank God for their blessing. Fast forward two years and he married his dad’s high school sweetheart. True story.
12. Fossil-Like Opinions
I once went on a date with a girl and this is how the conversation went: Her: “So, what’s your favorite book?” Me: “Tough, but when I was little I LOVED Jurassic Park.” Her: “Yuck, Jurassic Park.” Me: “The book or the movie? EVERYBODY loves Jurassic PARK!” Her: “I don’t believe in dinosaurs.” Me: “Fossils?!??!??!” I was already at the end of my rope, but her next response just blew my mind.
Her: “I don’t want to get into it, but I think fossils are BS.” I ended the conversation there and held onto the night. Until later on when she told me, “I don’t believe in outer space,” and my head freaking exploded.
13. Mission Failed
I wasn’t feeling great, but decided to meet anyway. We met at a Belgian bar. She was gorgeous, fun, and totally into me. I felt a gas pain, so I leaned forward slightly to quietly relieve the pressure. I completely and explosively pooped myself. The odor was immediate. I excused myself to the bathroom, but the damage was too great.
I walked out of the bathroom, muddy-panted, out of the bar, and boarded the train for home. The date was nothing compared to the horror of the following three weeks, recovering from E-coli.
14. Pics First
Back in high school a buddy of mine decided to try to set me up with one of his many chick friends who didn’t have a date to homecoming. Now, this guy has slightly different tastes in women than me, but I decided to go for it. I knew nothing of the girl I was going with until I met her the night of. She was unattractive physically and had a terrible personality.
Of course we went out got dinner and went to the dance and stuff, but that night was terrible from my perspective. Me and him now have a mutual agreement that if one of us is setting up the other, at least a picture, and some basic description of personality.
15. A Man of Many Interests
I went out with a guy from Tinder who turned out to be legitimately crazy. He regaled me with stories of how he attacked law enforcement, burned his arm to impress girls, spent significant time in a psych ward, and lost his virginity to an overweight working girl. He also told me that my eating disorder made him feel better about himself because it made me crazier than he was… He also told me I had obvious acne scars.
After our disaster date, he wouldn’t stop contacting me. He even went as far as asking me to stay in a rented house with him in another city. When I said no, he claimed I had ruined his entire year. I deleted Tinder immediately after that.
16. Quid Pro Quo
I went out for dinner and a movie with a guy one night. I tried to chip in money for both, but he insisted on covering it all. At the end of the night, we’re sitting in his car in the parking lot of the restaurant we had just eaten, and he asks me to sleep with him. He says, “I mean, I bought you dinner and took you to a movie, so it’s the least you can do in return.”
Thankfully, I lived nearby. I hopped out of his car and walked home.
17. A Picture Is Worth a Thousand Sweaters
I went on a Tinder date with a guy who is now in my contacts as “DoNotAnswer NaughtyPic.” Prior to the date, he seemed normal—but I was in for a rude awakening. We texted and talked on the phone, then arranged to meet at a local restaurant. He was cute, but definitely bitter about something. He was from California and apparently didn’t like this new city we were in. He started talking about really explicit topics and complaining about how uptight everyone here apparently is about it.
In the middle of dinner, he invited the waitress to a party that his company was throwing. This was after sending back the French fries he ordered. I showed him a picture of my dog on my phone. He then took out his phone and showed me a picture of his privates. We walked out of the restaurant together to get our cars from the valet. My car came first and I left.
He texted me later to let me know that he had my sweater. Apparently, I dropped it on the way out of the restaurant. He said that if I ever wanted to see it again, I would have to hang out with him. RIP, sweater.
18. The Cards Were Stacked Against You
I once took a girl out for lunch at a small little Chinese place. The food was pretty mediocre, so I didn’t really think much of it. I take out my card so I can pay, and the waitress informs me that they don’t take cards. I froze up. “Holy cow, what do I do??” Well, being the brilliant guy that I am, I asked my date to go get money from an ATM to pay.
As she was out, I thought I really just blew it. There was no way she was going to respect me again after I failed to pay for her meal. But to my surprise, it turned out she was laughing the entire time she was at the ATM and thought the whole thing was adorable. I got a second date. That time, we went to a REAL Chinese place that took cards. We ended up dating for almost four years.
19. A Shot in the Dark
A guy I was dating turned out to be a seller of illicit substances. While we were out for one of our first dates, he stopped in the middle of a bad neighborhood and left me in an abandoned parking lot alone for a good half hour so he could, “get something.” He came back with a jar full of every illicit substance you can possibly imagine.
During our kiss goodnight, let’s just say my hands “wandered.” What I thought was his belt buckle turned out to be a weapon. Naturally, my instinct was to say, “Hey, so why are you armed right now?” To this, he replied, “I just want you to know that when you’re with me, you’re safe. Hey, wanna go into the woods and shoot stuff?”
As soon as he said that, I lost all interest in hanging out with him. I began to worry that by “shoot stuff” he might have meant shoot me. So I politely turned down his offer to go and shoot stuff. However, I still agreed to see him again and I, unfortunately, continued to date him until he wound up behind bars. Not the best decision I’ve ever made.
20. Baby It’s Cold Inside
I once met up with this young woman for dinner. She was never married and had no kids. She got super weird and ended up saying a lot of crazy stuff. I could write an entire story about the evening, but here’s the kicker. At one point, I saw her eyes light up as she apparently remembered that she hadn’t told me something important.
“OMG, I haven’t shown you my daughter!” she shouts out. “Hmmm, what’s this all about?” I wonder. I thought she said she didn’t have any kids. The woman then reaches into her purse, pulls out an old Polaroid photograph, and hands it across the table for me to have a look at. I was not at all expecting to see what I saw next.
It was a picture of her sitting in a hospital room chair with some guy’s arm over her shoulder, both smiling at the camera. They were holding a stillborn baby! At this point, I had no reaction. It had been three hours into the night and an ever-increasing string of surreal events had broken my level of interest. I just handed the photo back and said, “I’ve got nothing to say about that.”
21. The More the Merrier
Here are some of the highlights of the night that I went on my worst date ever. First of all, the guy showed up two hours late. Normally, I would have just left, but we were meeting at a festival in a big city. I took the train for an hour. As I was getting off my train, he called to tell me that he missed his and had to wait another hour for the next one. We missed the festival as a result.
He had also lost his phone that day. So, not only was he calling me from a friend’s phone, but he also brought three friends with him. He and his friends brought a case of drinks and consumed all of them as we wandered the city and its parks. He made fun of me when I didn’t want to use some illicit substances with them on the same street my school was on.
Since I was starving, we went to a place that I ate at all the time in college. After ordering three drinks and dinner, he realized he forgot to mention that he didn’t have any money on him. At the end of the night, he shoved his tongue down my throat and grabbed my chest. In front of a large group of people, he exclaimed “You have an awesome body, it feels great!”
22. Four’s Company, Six Is a Crowd
My friend and I took these two girls in our class to our senior prom. We were all meeting up at a restaurant for dinner beforehand. We show up and the girls are sitting with two guys that graduated a few years ahead of us. At the time, we were just basically confused. We sat down and the six of us ate dinner. When we got to prom, the girls went in with us and the guys snuck in the back.
Turns out the girls just used us to get free dinner and prom tickets but brought their own dates.
23. For Your Eyes Only
I went on a date with this guy who seemed really sweet. We went out to a really classy dinner. The food was great, the atmosphere was fantastic…but at the end of the main course, he whipped out his phone and started showing me pictures he’d taken of his private area. Like…different angles, lighting, dynamic effects.
I rode with him to the restaurant, so I had to sit next to him on the ride home and fight the urge to fling the door open and tuck ‘n roll.
24. The Talking Cure
I had recently started dating this guy, and we were on our way to Circuit City to browse around for a few things he needed for his computer. While in the car on the way there, an annoying techno song came on and I commented on how I couldn’t stand how often they played it on the radio. He turned it up a bit, telling me that he liked the song.
I laughed and jokingly said, “OK, well I’m not talking to you until this song finishes!” I smiled at him and looked away, just enjoying the car ride. This turned out to be a huge mistake. We park the car and I immediately sense that something is wrong. He’s walking a few paces in front of me, clearly trying to avoid walking side-by-side.
I let it go and run to catch up to him. I take his arm and kiss him on the cheek and proceed to walk to the store with him. Again, he seems distant. I ask him what’s wrong and he tells me he’s fine. I let it go and decide to enjoy the shopping we were there to do. We’re browsing through the store, and suddenly I realize that he’s nowhere to be seen.
It’s around 7:00 PM at the time and the store was pretty crowded. I figure he must have wandered to another aisle and I do the same. 15 minutes later, there is still no sight of him. AT ALL. I’m walking through the store searching for him, and nothing. It’s now 8 PM. I call his cell phone and it rings out. I walk out to the car, and it’s empty. There are about six other stores in the complex and I wasn’t about to walk to each one searching for him.
It’s now 8:45 and I’m getting scared. The store closes at 9, so there aren’t that many people there. Finally, the store is closing and I walk out to the nearly empty parking lot. Well, there he is, sitting in the car. I run over with tears in my eyes, asking what happened. He looks at me calmly and says, “Now you know how it feels when the lines of communication have been cut.”
25. Stranger Than Fiction
I went out with a really gorgeous girl who I didn’t know was bipolar and off her meds. She wanted to drive, so we took her car. We went to dinner, which was fine, and then a movie, where she got more and more agitated and then excused herself. I thought she was going to a bathroom, then said out loud, “No, she’s bugging out,” and walked out and found her in the parking lot searching for her car.
She screamed at me that I’d been making fun of her, the people in the theater had been making fun of her, and the people in the movie had been making fun of her. I got her calmed down and got her home, and on the way found out that she was bipolar, she had stopped taking her meds, she was into self-harm, and the car was stolen.
She kept calling after that asking when we were going to go out again. Nope, nope, nope.
I went on a date with a guy who I met on the Internet. We decided to go get a coffee, take a walk around town, and if that all went well, we agreed we’d go see a movie. We met up and went to the coffee shop, where he slowly began to turn bright red and start sweating profusely. He played it off and said, “let’s go for that walk.” It was winter in Chicago, and somewhere around 15 or 20 degrees out, but I was game.
Obviously, the dude was nervous and I was hoping the walk would calm him down. Throughout the walk, he fluctuated between somewhat comfortable to being uncomfortable looking, but none of it was enough for me to take much notice. Nerves calm, right? After our walk, we agreed that we’d go to the movie. It would give him a chance to sit and relax, and we wouldn’t have to talk.
We were standing in line and he looked at me and said, “I can’t do this… I can’t do this, I’m sorry,” and ran away. Literally hauled his butt away from me. Later, I got an email from him saying I was prettier in person than he’d imagined, and so nice, that he just freaked out and couldn’t deal. It didn’t make me feel any better at all.
27. Forever Goth
I was set up on my first blind date by a friend who swore up and down that this guy was perfect for me. I asked her if he knew that I am basically a very geeky goth, and she said he had a thing for goth girls. We get to the restaurant and have a decent appetizer, talking about generic things like school, movies, and books and the server came by and took our orders. Then everything went haywire.
When she left, he clapped his hands together and said “Well, I guess we should get this out of the way. If we’re going to date, there are a few things you need to do:” He then gave me a laundry list of “tasks”: Lose weight, dye my hair brown, get a tan, dress in the clothes he picked out for me, remove all my piercings, remove my tattoos, don’t play video games.
I remember hearing all of what he was saying and just thinking “This is a joke. A TV host will jump out and tell me I’m on a joke show.” That never happened. People near us overheard this and began craning their necks, trying to look at me and see what was so “awful.” He ticked off all the things I needed to change and then sat back, smiled, and asked when I would be able to get started.
The server came back with our meals, and I have a lovely plate of pasta in front of me. I don’t know what got in my head, but I picked up my plate and dumped it into his lap. I left the restaurant, walked down the block, went into a convenience store, and called a different friend to pick me up, and told them the whole story. I cried a little and basically felt absolutely hideous. The person who set me up on the date was horrified, said she had no idea he’d do something so awful.
That was my first, and LAST blind date. It’s been a while since that awful day and I can proudly state that I am still as goth as I was then. And no one keeps me away from my SNES.
28. A Commonality
My friend in college set me up with this nice young woman because he thought we had something in common and would hit it off. Our entire conversation that night at dinner went something like this. I ask, “So, how did you meet John?” She replied with one word: “School.” I go on to ask, “Did you have a class together or did you live in the same building or something else?”
She says: “Same apartment.” Me: “I see. So, what do you do when you’re not in class or studying?” She replies: “Television. Music.” Me: “Did you want to do something tonight besides eat and talk?” She said no. After the date, I asked John what made him think that she would be a good match for me. He said, “Well, you’re Japanese(-American) and she’s Japanese (exchange student), so I naturally thought you two would get along.” Sigh.
29. The Sister
I went on a date with my buddy’s sister. I hadn’t seen her since we were kids, but by the time this happened, we were both in our 20s. She randomly started chatting with me online one day out of the blue. We talked a lot pretty much every day for a couple of weeks and really hit it off. So, we decided to get together to go to a movie.
Only, when I got there, I couldn’t pry more than two words out of her at a time. She only said “yes/no” and other one to two-word answers for very open-ended questions. I’m decent at keeping a conversation going, but I can’t do it all myself. I took her home, dropped her off, gave her a hug, said hi to her mom, then never really spoke to her again. Later, I found out the truth.
She was really into me and was just nervous. What a shame. Last I heard, she lives alone with her dog and is dating some dude out of state that is 25+ years her senior.
30. The Historian
I went out with a guy who, while we were walking downtown, would stop at every building and give me the historical background of each building. This isn’t a bad thing—the weird part was that he did each one in a different accent. Oh, but it gets worse. When it came time to cross the street, he did some ballet leaps all the way across.
He also asked me about all of my classes and knew details about them, when I had never told him which classes I was taking.
I was set up on a blind date with my roommate’s girlfriend’s roommate. It was actually a double-date, and we walked from their place to a Mexican restaurant nearby. On the way there, we saw my date’s ex drive by (they’d broken up fairly recently after a long relationship). She, apparently, was assured that we were all just going to dinner as friends and that this most definitely was not a date, so she vented about her ex several times over the course of the meal.
It wasn’t until I paid for her meal that she realized that it was, in fact, a date. I, of course, thought that she was a crazy girl, and I had just been burned by another crazy girl, so I was wasn’t going to make that mistake again. That was eight-and-a-half years ago. Right now, our three-year-old daughter is playing with her toy trains in our living room.
32. Running Away to Narnia
I got set up with the daughter of one of my parents’ friends. I wasn’t really looking forward to it, but I was on break from college, and she apparently went to school not far from me, so it wasn’t like a lost-cause summer romance type thing. They showed me pictures and said nice things about her. I picked her up from her parents’ place (we were both home for the summer) and was a little surprised by how pretty she was.
The pictures had been from when she was in high school, and didn’t do her justice. The date was dinner and a movie. Dinner went really well; we had a lot in common, she was very grounded and down-to-earth, cared about the environment. If I have a type, she was it. So, as we’re walking to the movie theater, I slipped my arm around her waist.
She pushed me away and got all serious. “I’m really sorry, because you seem like a nice guy, but…I’m a lesbian. I just went out with you to make my parents happy.” Sitting through The Chronicles of Narnia with her was the most awkward two hours of my life.
33. Manual Labor
Back in college, this really attractive girl in several of my classes started flirting with me, laughing at my jokes, asking me for help with the assignments, and complimenting me. After a few days, she asked what I was doing after class. She said that she needed to do a favor for her aunt, but that after that we could have dinner and “see what happens.” I was all over that.
I drove her to her aunt’s house to meet her. She introduced me to another guy who was already there and told him I was there to help. He showed me what we were doing, which was replacing a flight of stairs going up to her kitchen door (the ground floor was the garage and storage). I had never done anything like this before, but she was hot, so I was game. She disappeared as soon as we got started.
About 30 minutes in, we had the stairs assembled. It was a kit and the other guy knew what he was doing, so it didn’t take too long. We wrestled everything into place. We hadn’t spoken too much beyond instructions, so I eventually asked “So how do you know Julie?” thinking he was probably a cousin or something.
He responded with, “Oh, we’ve been dating for about a year.” I froze up, and he looked over at me. “Oh shoot, man! I’m so sorry! I thought you were just a friend from school. She’s done this before, but she promised me she’d stop.” He went on a little about how she likes to manipulate guys to prove she’s still “got it.” At one point, he said, “I’d leave her, but things in our bedroom are incredible!”
I made some remark about wanting to get revenge, and we both had a laugh over it. He was actually pretty cool about the whole thing and insisted that I take $60 from him for my time and effort. She came back with a bag of McDonald’s for me. I guess that was what she meant by “dinner.” I drove home alone. She hardly spoke to me in class after that, which was fine by me.
Any time I saw her flirting with a guy from that point on, I’d quietly warn them off.
34. The Devil Is a Gamer
Small background on my life at the time: I had just opened up a LAN Center, I had been working every day for the last four months to prepare for the opening. So, my friend set me up with a friend of his wife. I picked her up and took her out to this nice restaurant in town. Trying to decompress from a full four months of work was a little bit difficult, but I managed to not talk about work at all.
We picked up on interests and things we like to do outside of work. Since my work at the time was games, I didn’t really bring up that I played games and ran a LAN center. Somehow the conversation turned into major dislikes and turnoffs and she brought up how much she hated gaming. She went on a five-minute tirade on how games are the devil and those who sell them and enable children to play them are the problem with society.
Computer games are going to be the downfall of society as we know it and she won’t have anything to do with them. I quietly sat there listening with a dumb grin on my face which she interpreted as agreeing with her. She finishes talking and then goes, “So what do you do for a living?” I sat there for a second thinking how to respond—but then I finally came up with the perfect answer: “I’m the devil and I corrupt kids’ souls.” She freaked out and hurried out of the restaurant. I don’t think she got the joke…
35. Speaking His Mind
I once met a guy from OKCupid. He seemed nice, but never stopped talking. After he interrupted me for the third or fourth time, I finally asked him “Do you actually want to hear anything I have to say?” He apologized profusely and said, “You’re right, I’m so sorry!” He then pulled out a pad of paper and a pen, and proceeded to jot down notes as I was telling him about myself and whatnot. I finally asked him what he was doing.
He replied, “Oh, I’m just writing down things that I want to tell you when it’s my turn to talk again!”
36. It Bet This Date Was a Lot of Fun
Early college first date: She wanted to go to the horse-racing track for the day. When we arrived, she took me to her family’s box seats…and her family members were all there, waiting for us. She knew ahead of time that they’d be there, but didn’t tell me. It felt like an ambush. It was a very long, tedious day of races and betting, followed later by a seemingly endless dinner at her parents’ house…where they talked exclusively about gambling, horse-racing, and high-stakes betting.
I couldn’t wait to go home and get away from all of them.
37. It’s So Hard to Say Goodbye
I once went on a date with a girl who I met on a dating app. We decided not to talk at all before we met up, kinda like a real blind date would have gone before the internet. So, we were both excited and set up to meet at an old bar in the city. I got there early, and she arrived five minutes later. We talked for a bit and then she suggested we eat.
I wasn’t super hungry, but I got something anyway. She ordered about four drinks. During our conversation, we realized that we had a lot in common. We had even worked at the same place about a month apart! We also liked the same movies, music, etc. It was honestly an amazing night—but I never expected it to end how it did. At the end of the evening, I asked the waitress for the check.
While I was waiting for it to arrive, my date said that she needed to go to the bathroom. She then got up and walked straight out the door of the restaurant. Just right out the front door, adios. I went back to my phone to ask her why she did that, but she had already deleted her account. I’m not entirely convinced that she wasn’t just a very hungry ghost!
38. Dinner and a Show
I would have to say that the worst date I ever went on was the one with the girl who came to my house to “make me dinner.” She showed up with a bottle, popcorn, and a movie. We consumed it, and she decided it would be fun to run around our neighborhood, screaming and doing cartwheels in the streets. I said sure. Out we went.
She climbed a tree. I climbed the tree after her. We slept together in the tree. What was so bad about this date, you ask? One of my annoying, silly sperms decided to go and fertilize one of her eggs. She had a miscarriage when she was about three months along. I was not looking forward to having a child with this crazy girl…
39. Pop Goes the Weasel
I once went out on an eHarmony date to a high-end bar with a huge drink selection. The girl shows up and she doesn’t look anything like her photos. She proceeded to drink seven Miller Lights, then proceeded to tell me some very weird things. For example, she told me that the reason she didn’t want to be single anymore was that she missed having someone to pop the zits on her back.
At the end of the date, she asked if I wanted some gum. I politely declined. She went in for a kiss and I turned it into a hug instead. Needless to say, this was the first and last date that we had together. No zit-popping for me.
40. Leaving Out a Key Detail
I met her in an adult soccer league. I asked her to grab breakfast that weekend, and she accepted. I picked her up, took her to a hole in the wall diner, and ordered the garden omelet. Throughout the entire meal, she talked about all the crazy stuff that she was into in the bedroom. I eventually got the check and then realized that my wallet was still in my gym bag from the night before.
I apologized, she paid for us both, and I went back to her place. She invited me in, and I couldn’t refuse as she had just bought me a meal. An hour later, after one of the wildest experiences of my life, we were lying in bed relaxing when she suddenly got a text and started to panic. “Oh my God, you have to leave now! My boyfriend got off work early and if he finds us he’ll kick me out!”
This was the first I’d heard of her having a boyfriend, and I suddenly realized that I had just slept with a woman on her boyfriend’s bed after she had bought me breakfast with money he had given her. Uh oh…So, I threw on half my clothes, jumped into my car, and knocked over their mailbox with my bumper in my rush to get the heck out of there.
When I got home, I discovered that my rear bumper now had a nice new crack in it. I guess I’ll always have something to remember that day by!
41. A Storied Romance
I once decided to try online dating. The guy I went out with had looked pretty cute in his picture. He showed up to my house when it was time for the date. He did NOT look anything like his picture. I later came to find out that the picture was him from five years earlier—and that he had gone through a BAD case of adult acne since then, which was still plaguing him.
We went to Long Beach and he said he wanted to go to Ruby’s or some other diner like that. As soon as we sat down and the waitress had handed us our menus, he informed me that he only had a little bit of money on him (something like $20). I inferred that this meant I had to order something cheap.
I ordered a basket of fries and a glass of water. He then proceeded to scarf down a bacon double cheeseburger, onion rings, and a strawberry malt—in addition to about 75% of the fries I ordered. I wish I was joking. Throughout the meal, he repeatedly lamented his last girlfriend, who had recently left him. He was practically in tears over the fact that she didn’t love him anymore, and he told me about how he wanted her back so badly.
I sat in stony silence the whole time. Clearly, I was just intended to be a sounding board to him. The date wasn’t really a date. It was a hostile kidnapping in which I was starved and had to listen to the ravings of an idiot.
42. An Unholy Alliance
I’m an atheist, and I mentioned that fact on my online dating profile. In my bio, I stated that I’m fine with religion but that it just isn’t for me. Nevertheless, I go on a date with a girl from the site and she asks me what church I go to. I say, “Actually, I’m an atheist”. And she flips her lid. “How the heck could you waste my time like this?? It clearly says I only want a religious man in my profile!”
From there, she goes into a rant about how terrible atheists are and how I’m going to burn in you-know-where. She was bad enough that the manager came over and asked us to leave. So when I got home, I started thinking that maybe I had her confused with another girl I was talking to. I pulled up her profile and there was literally no mention of religion anywhere. For her match’s religion, she put “no preference.” For her religion, it was “I’ll tell you later.”
43. He Shoots, He Doesn’t Score!
I went on a double date back in high school. It was me and my friend with two girls. We stopped by the local bowling alley and reserved a spot. The expected wait time was thirty minutes, so we wandered around and stopped by the two air hockey tables. For some reason, they were only about three inches apart from each other.
We decided to play. The girls played on their table and we played on ours. Theirs was a display of low-level motor skills that culminated in synchronized giggles. On the other hand, my friend and I were hosting an unofficial air hockey final. As we were going back and forth in full force, I accidentally chipped the puck.
The puck conveniently went flying to my right, nailing my friend’s date square in the forehead. Annoying giggles quickly turned into annoying cries, and the girls ran off to the bathroom. My friend and I looked back at each other and instantly knew two things: 1) the date was over, 2) we had to finish the match. And so we did.
44. From Weird to Weirder
I had met this girl online. She was a friend of a friend of mine. We got to talking for a bit and we eventually decided to hang out. She lived about 30 minutes away from me in the middle of absolute nowhere, so I had to drive up to meet her. Since I was not familiar with the area, I asked her where she would like to eat.
She says, “Oh, well my favorite restaurant is not too far from here. We can go there. It’s really fancy and expensive, though.” I told her that I didn’t really mind and that I was willing to go wherever. I asked her what the restaurant was called. She says, “Oh, it’s Red Lobster.” Now, I’m not one to care about how much money people have, but I was quite shocked that she thought Red Lobster was a high-class establishment.
However, I let it slide, because maybe to her Red Lobster is the epitome of fine dining. Turns out, Red Lobster is another 30 minutes away. On the way there, we passed a handful of other restaurants. Olive Garden being one of them. This is one of those details that gets dropped in stories very nonchalantly, like hmmm I wonder if this will be important later.
Anyway, we get to Red Lobster and the hostess is walking us to our table. She seats us, hands us our menus, and begins telling us about the specials. Before she is even able to finish, my date blurts out, “I already know what want!” It was so awkward. She didn’t say it in a rude way, she more said it in a more excited way.
She said it as if it was totally awesome that she already knew what she wanted and everyone needed to know. Anyway, the hostess is stunned and just kind of walks away. Eventually, the waiter comes to our table, and she orders. She gets, “Shrimp Alfredo with no shrimp.” At this point, I’m completely stunned and wondering what her deal is.
She made us drive 30 minutes, which is a long time to spend in a car on a first date, just for some fettuccine alfredo. Clearly, this was the best restaurant choice for that and not the Olive Garden. I still let all of this slide, because at this point she just seemed extremely eccentric and I thought that maybe if I got to know her better than her behavior would seem less odd.
After dinner, we are closer to my place than to hers and she wants to go back to my place to watch a movie. I oblige, obviously. We get back there and I ask her what movie she wants to watch. She picks Happy Feet. Yes, freakin’’ Happy Feet. I guess at this point it’s my own fault for even asking. So we start watching Happy Feet.
She wastes no time in starting to kiss me, so I don’t make too much of a fuss. Now, the clothes are coming off to the soundtrack of Happy Feet. Really awkward. She starts talking about how great she is in bed. This was surprisingly not as awkward as it could have been, Happy Feet aside, and it was effective in keeping me interested.
Then she insists…no, demands that she remove my pants using only her mouth. Now, I can see how some people would be into this, but not me. I tried to talk her out of it, but she was convinced that she was going to be able to do it. And bless her heart, she did. Button, zipper, and all. It was still just a really odd thing to do. Especially on a first date.
Then, right when we were about to sleep together, she stops, looks up at me, and says, “I don’t mess around with guys that are not my boyfriend. So ask me to be your girlfriend.” So I did. We dated for about three weeks after that and she only got more crazy and weird from that point on. She actually got married a little while back, but before doing that she contacted me on Facebook to see if I wanted to have one more try with her.
I politely informed her that I would not be interested, to say the least.
45. Looking Out for Number One
I once had a guy tell me that he wanted to take me out to dinner and a movie for our first date. Before the movie, he said he was hungry and he went through a drive-thru. He ordered himself some food. He never asked me if I wanted anything. After we pulled out of the drive-thru, we sat in a parking space while he ate his food.
After he finished eating, he said, “Oh, sorry, did you want something?” Then, we went to the movie theater. We went to the concession stand. He again didn’t even bother to ask if I wanted anything. He got himself a large drink. As we were walking away from the concession stand, he said “You can have some of mine.” Gee, thanks!
46. Second Impression
After our date, he gave me a verbal report card in the car. One of my negatives was that “I took too small of bites.” Apparently, my good table manners made him nervous? But one of my positives was that it seemed like I liked to be in the kitchen? About two hours after the date, he called me to tell me that he had looked through my entire Facebook and read all of my blog.
He had decided that I was cooler than he’d thought on our date, so he called the girl he had plans with the next night and dumped her to hang out with me more. Needless to say, there was no second date.
47. Magic Man
I met him on OkCupid after a serious breakup, and we talked for like two weeks. Seemed completely normal. He was a cello player and pretty smart from what I could tell. We decided to meet at a Starbucks and the conversation was good until he started doing an impression of the Joker. I’m already freaked out at this point and ready to leave.
Then he asked me why I hadn’t drank my coffee yet, and I said it was still hot. That’s when he told me that he was getting into the elements, and slowly has developed the ability to control fire. He apologized about the coffee, because he was in control of the heat and fire around us. I was intrigued at how ridiculous this was and let him continue.
He told me that he first learned of this when he was in his car and the car windows steamed up. I was trying so hard not to laugh. I politely said well this was fun, but I need to get to work.
48. Most Unladylike
I went on a blind date. The girl had an okay profile, of course single, no kids, seemed intelligent enough to not type like a four-year-old. I dressed nicely, and picked her up promptly at 7. She seemed nice enough, and I took her to see a movie. The actual movie was not important. It was what she did during the movie.
Throughout the entire film, she talked in almost a shouting volume, put her feet up on someone else’s chair, and threw popcorn into the audience. I was mortified to be associated with a girl who was so obnoxious, so I figured I would take her to eat, then cut my losses. I took her to Cheddars, where she could at least talk.
When we finally got a semi-decent conversation going, it went off the rails again. The server came out with a tray of drinks. She grabbed hers, then said that they brought her Coke and not Pepsi. When the server returned, she dumped the whole glass of soda on him, and demanded a refund for the meal that I was paying for! I was disgusted at this point.
Finally, I took her outside after dinner to explain that she was a nice enough girl, but I didn’t think the experience deserved a second date. She went insane, throwing rocks, trying to take my keys, etc. I never saw her again, and I don’t want to repeat the experience.
49. The Garbage Bag
My dad had been set up on a blind date by his friend. As he picked up his date, he noticed she was carrying a strange bag, not a purse or anything normally brought on a date, but a garbage bag with stuff in it. He kind of shrugged it off, and they got in the car and started driving. During the car ride though, he noticed what was contained within those bags and his blood ran cold.
It was two baby dolls with blood smeared on them. He asked her why she had brought two dolls, and she just nonchalantly responded, “They’re my children.” My dad instantly felt that this girl had some problems, so he stopped at a gas station and asked her to go inside to get him cigarettes. He immediately drove off, abandoning her at the station with her two bloodied dolls.
When he talked again with his friend who had set up the date, his friend said, “Oh yeah, I forgot to mention. She had two abortions in the past two years, so now she carries around those dolls and claims they’re her children. I thought it was no big deal.”
50. A German Girl
A number of years ago, I met this German girl at the bar I bounced at. She was kind of cute, really smart, and knew more about music than almost anyone I’ve ever met. She says that we should hang out sometime, so I mention this jazz bar that has an amazing open mic night on my night off. She says yes, and we make plans.
We meet at the appropriate time at an open mic night at another place, but she barely talks to me the entire time. Neither of us drives a vehicle, so we jump a bus to a nearby restaurant to eat. Then she mentions a piano bar so we jump a cab over there. All this time, she is talking about her roommate and how she is worried that he doesn’t have health insurance.
That’s just a little strange until she talks about how she was discussing that situation with his mother. Warning bell kicks on like crazy. Turns out that her roommate is actually her fiancée and she believes that she is pregnant. She hadn’t been to the doctor, but “a woman knows these things.” So, we get to the jazz bar and I get loaded off my butt because I know this isn’t going anywhere.
The music, as always, is great, but since we’re both taking public transit, we have a different problem: the buses have stopped running. So, she ends up calling her fiancée to pick us up. As fate would have it, I have a good friend who lives pretty close to them, so I was able to go over there and get away from them. Yikes.
51. TGI Forget About It
Two friends and I are hanging out one day when we get a call. It’s our mutual friend. He wants us to come to dinner with him and his girlfriend. They wanted to go to TGIFridays. We politely decline and tell him that we are all poor college students and TGIFridays isn’t very good. We invite them over and offer to cook (my buddy is actually a really good cook).
Thirty minutes later, we get called again. It’s not our friend, it’s his girlfriend. She wants to know why we aren’t coming to TGIFridays. We reply that it is expensive and that we’d much rather cook for her and her friends (we learned earlier that she was actually trying to set us up with three of her friends).
“But it will be better! You’ll enjoy yourself!” “I’m sorry, but we can’t really justify spending that much! We have food here, we’d love to meet your friends, but we don’t want to go to TGIFridays.” “Oh, come on,” (patronizing tone of course), “if it’s that big a deal, I’ll pay for you.” “That’s not necessary. There are three of us.”
She continued to whine and patronize us and finally put her whipped boyfriend (our mutual friend) back on the phone. He whines to us some more. We reluctantly agree to go as long as she lets him come out with us on Friday night. Fast forward a few hours, we get to TGIFridays. We meet our friend and his girlfriend and three girls from her church group.
We tried to be civil, but they were just so boring, very Christian, and incredibly snobby. We had no desire to be there. So, we broke out the emergency stash. All five flasks of it. Got incredibly loaded. America’s Funniest Home Videos was on the television. So much funnier when intoxicated.
We got really loud and migrated to the bar to watch a basketball game. My buddy ordered a slice of cake and managed to get none of it in his mouth and most of it on the floor/table. He then heard someone with a New York accent and went over to ask them for their driver’s license so he could compare it to his fake, as NY IDs are apparently really easy to fake.
The guy was cool about it, but we were still asked to leave. We tipped pretty well if that’s worth anything.
52. Real Men Get Lost
I have a story about a date that didn’t even get to happen. I got set up to meet somebody off the internet, who lived about an hour away. He was going to come into the city, and we would meet for lunch, go to the local Aviary, be all giggly and stuff, and hang out with some birds. Then (because I am a very emancipated woman) maybe come home for the naked fun times.
I didn’t know a whole lot about him at all, but I was willing to entertain the possibility, and it had been ages since I’d been on a date—working too hard, studying too much. The idea of a relaxing day was really pleasant. He was supposed to pick me up at noon. At 12:30, he calls and tells me he’s lost; he thinks he knows where I am, I should just hang tight.
What followed was SIX HOURS of getting a phone call every hour where I offered to come and find him, and he said nope! Nope. A real man doesn’t accept handouts like that! I made lunch, ate it. Watched a movie. Read a book. Spent a stupid amount of time on the phone listening to him curse at the city, the drivers in the city, the road signs in the city, and his car.
Finally, at nearly 7:00 pm he says, “I think I’ll stop at another gas station and get more directions,” and I just cut him off right there. “No. Sorry. No. Go home. This isn’t going to work. I’m ticked off and frustrated with you. Just go home.” “But aren’t you gonna give me a chance?” “Go home!” And then he called me the b-word and I hung up on him.
Went and played some video games. The end.
53. When Age Isn’t Just a Number
I was volunteering at a university orientation market when we met. Cute girl, had a nice chat, set up a date. I think I was 22 or 23 years old at this time. When the day comes, I pick her up at her place. Turns out she lives with her mom. They have a rather childish argument in front of me about whether or not her bicycle lights are working, but alright. Moms will be moms, right?
We have dinner and talk about this and that. She tells me about her horse. I tell her about the time I tried horseback riding as a kid and we both laugh. She talks about an actor who she thinks is sooo cute. Instead of taking a walk downtown after dinner, we decide to go see the latest movie with that actor because why not. It’s kind of chilly out anyway.
During the intermission, we talk about music and she hasn’t heard of any of the bands that I listen to. I thought that was odd, because they were all fairly well-known. I ask her about the music she likes, and she mentions a whole bunch of current boy bands. I’m now starting to have a horrible hunch. I tentatively ask her a few more questions. Eventually, I give into my sinking feeling and ask her the fateful question: “How old are you?”
It turns out she’s fourteen. The guy behind us just about chokes on his popcorn as he realizes what’s happening. Turns out she wasn’t at the orientation market to find a program of study, she was just tagging along with her older sister whom I had never met or heard about. Perfectly lovely person, but I felt so stupid.
54. He Finally Opened His Mouth, and That’s What Came Out??
My worst date ever was my first ever OKCupid date. The guy shows up still talking on his phone, looks me up and down, and then silently motions for us to go into the restaurant. It was a Lebanese place, but he immediately declared: “I don’t really like African food.” At this point, I was just waiting for my roommate to meet me outside later so I could tell her about this disaster—but it got even worse.
While I was waiting, he continued talking long enough to inform me that he had written a musical about historical tragedies. That’s normal…I also paid for dinner because, in his own words, he was a “feminist.” Ahhh, Brooklyn!
55. Weighing Her Options
I once went on a date with a wealthy, bigger woman who was used to always getting her way with men. We had become friendly over the past few weeks due to mutual friends and hanging out at social gatherings. She asked me to go drinking with her, so I said sure. When we got to this little hole in the wall bar, she introduced me to all her drinking friends.
I’m assuming they were the people who frequented this bar. Anyway, she started trying to aggressively make out with me at the table in front of her friends. I tried to tone things down, and she then started complaining about how shy I was being. After I told her that I didn’t feel comfortable, she decided, in front of the whole bar, to yell out, “HOW MUCH WEIGHT DO I NEED TO LOSE FOR YOU TO DATE ME??”
I quickly got the impression that I was no longer welcome at that bar. If everyone’s looks could kill, I’d be gone 100 times. I left quickly.
56. Cat’s the Way I Like It
This happened to a lesbian friend of mine. It was a blind date that she had met through a personal ad in the local paper. This was before internet dating was a thing. My friend shows up at the woman’s house. It’s cluttered with all kinds of garbage and the woman talks nonstop like a speed freak, mostly about herself and her neuroses.
So they decide to go rowing on the nearby lake, and the woman insists on bringing her cat along on the boat. Yes, a furry, live house cat. Turns out she never went anywhere without schlepping the poor cat along. As weird as that seemed, my friend went along with it. She got through the date and never contacted this woman again.
Funny epilogue, though. Many years later, that same friend met her current partner. It turns out that her partner also once went on a blind date with the cat lady! We couldn’t believe it when we first realized this. Discovering that fact made us wonder just how many first dates this woman has been on. It really is a small world after all!
57. Not What She Was Expecting
Ugh, I’ll never forget this one. So a couple of weeks after my girlfriend had broken up with me and moved out, I was hanging out at the local handball courts when I met this young cutie. We set up a date and I picked her up in my fancy date pants and shirt. I took her back to my pad to watch some movies and we really hit it off.
She was admiring the pictures of me around my room and my mom was hardly intrusive at all. We got to know each other pretty well, so I did what any rational mammal would do: I presented my privates and proposed we hook up. But get this: the girl just gets up and BOLTS! I guess we were not on the same page at all, and I just didn’t catch on early enough.
58. Two’s Company, Five’s a Crowd
I once went on a date with a girl from OKCupid. It was latish (about 9 pm), and she sent me a message out of the blue. We talked for a while, and she wanted to meet up for food. I hadn’t had dinner yet, so I agreed. We were to meet up at a local diner. Her profile picture was reasonable. Not my typical type, but not awful. What showed up, however, was not great.
She was about 5′ 2″ and somewhere between 190-210 pounds. Rotund is the best word. That would have been fine if she didn’t also look like a toad. I’m trying to be nice here. Now, that too would have even been okay, but it wasn’t just her! She had brought her friend along (a 16-year-old). For some context, I was 22 and she was 20. To compound that, her friend had brought a toddler along, as well as another friend.
So here I am with three girls and a toddler that I don’t know. All three of the girls had brought energy drinks into the restaurant with them. We sat down at the table and it just went downhill from there. The toddler ran out of juice in her sippy cup, so one of the girls filled it with the energy drink. She then let the toddler play with the sugar container on our table.
She promptly spilled sugar all over the place and started licking it up. Meanwhile, the three girls were just laughing at the toddler and having a great time. They started talking amongst each other and not even attempting to include me in the conversation. After about five minutes of ignoring me, they started talking about guys from high school.
To make a long story short, I ate half a chicken sandwich, excused myself, apologized to the waitress for the mess and the awful people, left a $50 bill, and got the heck out of there.
59. Falling Behind
A few years back, there was this guy who I knew and liked. He was handsome, a little older, and fun to be around. Let’s call him “D.” So one day, “D” calls me up and asks if I want to come and hang out at his place. I agree, and “D” says “Cool! Just so you know, I have a few friends over, but they’re leaving soon so come on over and we’ll see where the night goes.”
“Not a problem,” I say. I’ve partaken in that activity from time to time in the past, so it certainly wasn’t a deal-breaker. Well, I show up and his friends are still there. Again, not a problem. When it comes to just hanging out, the more the merrier! So as I sit down, I find it odd that I don’t smell anything like I was expecting to smell. When I realized what it was, my blood ran cold.
Sure enough, they were into some serious stuff. They were using extremely dangerous substances. So, I politely declined to participate and began to contemplate my escape. “D” and I started to chit chat and I noticed that he was not participating either. So, I thought to myself, “Great, maybe his friends are users, but it seems like he’s not into it.”
A small time passes, and it stops feeling awkward that people are doing this around me, especially because the host and I aren’t partaking. “D” then calls me into the other room and closes the door. He proceeds to start kissing me. Given that we had made out in the past, it wasn’t that unexpected or a big deal. “Finally!” I think to myself, “The night is going somewhere!”
Well, as soon as I get that thought out, he pulls down his pants. Ooookay? Forward, but not necessarily unwelcome. He pulls away from me and reaches into his dresser drawer. From there, he proceeds to pull out a piece of tin foil filled with a huge sample of the hard substance. “Hold this,” he says, before grabbing some lotion. He then shouts: “Shove this up my butt! That’s the best way to use it!”
I don’t remember exactly what my reaction was or what exactly went down next. All I remember is being sure that I was not interested in following that instruction. I seem to remember saying that I was allergic to the lotion. Smooth, I know. Then, I remember pretty much running out of there like a sprinter after saying my abrupt goodbyes.
60. Standing on the Corner
I asked a girl out in late spring, so we decided to walk around outside. It was nice out and she went to a different school than I did, so she showed me around campus for a while. It was pretty interesting. She was probably slightly out of my league, but I thought things were going well. We decided to grab a bite to eat at a place in the nearby bar district and sat outside.
Halfway into the meal, a local wanders down the street playing a harmonica and just rocking out. We barely even noticed him because things were going pretty smoothly. We had just discovered that we enjoyed the same kind of music and were deep into a conversation about that. Then, all of a sudden, we hear a lot of shouting and swear words.
We look over to see that another local man had appeared on the scene, angry at the first guy about who owned that particular spot of the street corner. The fight got pretty heated. We tried to ignore it, but it was slightly impossible as they were only about ten feet away from us. I still can’t believe what happened next. All of a sudden, the second guy pulls out a knife and stabs the first guy in the neck.
He passed really quickly and blood was everywhere. It was horrific to witness. We were then questioned by the authorities and had to make statements and everything. It basically ruined the entire evening. Somehow, I got one more date out of this girl, but we just struggled to make conversation at that point. After witnessing a murder, things were just really anticlimactic.
61. Fourth Quarter
In high school, I took this girl out to dinner and a movie as a first date. It was mostly as a courtesy to a friend, because this girl would always be the third wheel on all of their dates. We finish up the movie and I am driving her home when she says to take a turn here and there to make it back to her house. Turns out, she had decided that it would be prudent for me to meet her grandparents.
This is fine enough with me, as I tend to have an easy time mingling with the golden oldies. However, it is about 10 minutes before her curfew when we arrive at her grandparents’ house. Before we even walk in, I tell her to call her parents and let them know why we are running late. She puts up a fuss and says they won’t care and that I shouldn’t worry.
Time goes by, and we end up at her grandparents’ place for an uncomfortable 30 to 40 minutes. All the while, I am telling her that it is past her curfew and that her parents don’t know we are there and she should let them know. We eventually make the 15-minute drive back to her house and I am feeling completely uncomfortable the whole way there.
The moment we arrive, her mother rushes her into the next room and some mumbled yelling occurs. I’m sitting at a table when the father comes into the house and gives me an angry look before yelling some more. This is all a bit much for me, but I handle it okay and go home. At this point, I’m just glad to be leaving and not even thinking about what could be coming next.
As soon as I walk into my house, within my curfew mind you, my mom starts yelling at me, “WHERE THE HECK HAVE YOU BEEN??!!” I’m immediately wondering what in the world is going on. Well, it turns out that, while he was waiting for us to return, the girl’s father drove to my house and started banging on the door and yelling at the top of his lungs.
Apparently, he was shouting that I have his daughter and that he wanted her back. My mom doesn’t know who this man is and, in the panic from beyond the locked door, she heard his shouts as, “YOUR SON HAS GOT MY QUARTER! YOUR SON HAS MY QUARTER AND I WANT IT BACK!”
My mom freaks out, thinking there is a psycho at the door. She grabbed a weapon and called my uncle from across the street. My uncle also grabbed a weapon and yelled at the guy from across the road to either leave or that he was going to get shot. Meanwhile, my mom is politely yelling back through the door, “IF MY SON HAS YOUR QUARTER, HE WILL GIVE IT BACK TO YOU TOMORROW!” to try to appease him.
The guy eventually leaves, but not before my mom becomes completely terrified and confused about what she had just witnessed. I finally explain the situation to my mom and convince her that the girl’s family is crazy. She breathes a sigh of relief and we both have a good laugh about it later. However, this has to be the WORST DATE EVER!
62. He Has a Lot to Say
I once went on a dinner date with a guy who had dined at that restaurant before and complained about the food to me and the waitress before we had even ordered anything. He also interrupted me. A lot. Once, he interrupted me to improvise a commercial he’d been thinking about. His exact words: “I may not be a tenured professor, but I do love grapefruit.”
Umm, what?? I’m sorry, but I have no idea what you’re talking about, buddy. We also shared no interests. So, naturally, he just talked about himself for the entire date. Awesome. Everyone knows that there’s nothing a girl wants more in this world than to spend an evening hearing about grapefruits and how great someone is…
63. Brotherly Love
I once met a girl on Facebook and went out with her on a double date. I brought my best friend along, and she brought her best friend too. Her brother was there when we met up to go see the movie. This seemed okay, as I thought he would just be there to check out if everything was okay. Then, it turned out he was staying to watch the movie with us.
None of this had been mentioned to me beforehand. I’m a very shy person and I find it hard to talk to girls at the best of times. Him being there made it nearly impossible for me to talk to her. My friend hardly said anything the whole night either. In fact, at the movie, he sat in between me and the girl. She apologized after the date about it, but we gradually stopped talking.
Not long after, my friend started talking to her on Facebook. They’ve now been dating for three years. Lucky me!
64. Don’t Call Me
I was set up with a friend of my roommate’s girlfriend. Let’s call the date “Lisa” and let’s call the roomie’s gf “Karen.” I knew what she looked like so I knew there was an attraction but I had never spoken with her. We met outside of the restaurant and Lisa was on her cell phone. I figured it must have been important, but as we walked in and waited for the table she kept talking about stupid junk.
She was clearly on the phone with a BFF about nonsense. She gets off the phone, doesn’t apologize, and we get seated. About two minutes later her phone rings again and it is the same, “OMG, no way!” garbage conversations. The waitress comes over and we order drinks…while she is still on the phone and I twiddle my thumbs.
The drinks come, Lisa is still on the phone….I’m half done my drink and have waved the waitress off once already because Lisa is still on the phone. I’m not proud of what I did next…ok, I’m a little proud. Finally, about 20 minutes into the call, I quietly stand up, take $20 out of my wallet, and walk out without saying a word. As I’m walking out, I see Lisa’s eyes widen to the size of dinner plates, her mouth open wide, and her face turn red in embarrassment (all of the surrounding tables had seen what transpired and were whispering to themselves about it).
By the time I got home, my date Lisa was on the phone with Karen who was over at our house at the time. It didn’t occur to me until now that my date was probably on the phone with Karen the whole time! Karen was furious. As soon as I walked through the door, she started attacking me with, “You are such a jerk, why would you just leave her there and not say anything!?!?”
I looked her dead in the eyes and calmly replied, “I didn’t want to interrupt such an important phone call,” and then walked into my room and went to bed. As I was leaving the living room, I noticed the same expression on her face that Lisa had when I left the restaurant.
65. No Match
When I was very young, probably around 12 or 13, an older friend of mine asked me if I wanted to go to a shop with him. I said I didn’t have any problems with it and happily went along. On the way there he said he was meeting up with a girl and asked if I’d mind talking to her sister. Her sister was severely handicapped and in a wheelchair.
Of course, I didn’t find this out until I met her. The girl then decided she didn’t like me and proceeded to insult me.
66. Simply Irresistible
First date: Drove around the countryside, explored an abandoned building, went to the beach, had a great time overall. Second date: Arrive at a college jazz show, she is sitting with another dude, holding hands. I sit in the back of the room, bewildered, while she turns around every few minutes, just grinning at me unabashedly.
Third date: Drive around town, goof off in random stores, spontaneous makeout session at a stoplight, cause a minor traffic jam. Fourth date: Arrive to pick her up for the date, and she is chatting up another guy. Car drives up, she gets in and leaves, leaving me with some random dude who ends up crying. He turns out to be suicidal, cries on my shoulder for several hours, we get burgers and talk about life, and have a strangely decent evening in the process.
Fifth date: Screw that. I stayed home.
67. An Eerie Transformation
When I was trying to date this girl, I found out about her deepest secret the hard way. We had just finished watching a movie in her dorm room when she started freaking out as she looked in the mirror. I asked her what was wrong, to which she replied “She doesn’t want you here,” and immediately kicked me out of the room.
As I was standing outside in a dumbfounded manner, I decided to text her because I wanted to know what the heck just happened. As I was walking back to my place, she texted back gibberish and stuff about her hurting her. I didn’t understand, and I immediately walked back to her dorm. She texted me to go away. I told her no and that I was waiting for her to come let me in so I could help her.
She came down and let me in. She ran back to her room and I followed. The room was extremely dark and I could barely see anything when I closed the door behind me. There she was on the floor, staring at a door mirror. She slowly turned her head at me and stared at me. It was like that for a good minute. After officially being creeped out, I asked her what was wrong.
She snapped out of it for a second. It was physically visible in her face that something changed. She told me that she was having trouble with her “other self.” It took a couple of minutes, but she eventually “changed.” She went limp and slumped over. I rushed to her but didn’t know what to do. She woke back up but definitely not herself.
It took hours for her to stop “changing.” I didn’t know how to handle her, but I eventually got her to get help after that.
68. Take A Hint
A couple of years ago, I met a guy and sort of pity-dated him for a couple of weeks. He started off seeming like a decent enough fellow, but there really wasn’t any spark at all, at least not on my side. Being naïve and rather inept on the romantic front, I did what amounted to unwittingly stringing him along by deigning to go out with him for coffee and dinner now and then.
It was still quite clear that nothing else was going to happen any time soon, barring some freak accident in an aphrodisiac factory. One day, I was hanging out with him, my best friend and his boyfriend, and a lesbian friend of mine who was visiting all the way from Austria. Pity-Date and I were in the minority as straight people.
Lo and behold, he started making horrible comments under his breath, within clear earshot of my three gay friends. I took him aside and gave him what-for; I don’t tolerate that kind of stuff from anyone in any company, let alone from my date in the company of my good friends. He assured me that he had every right to say this stuff because his mother is, in his words, “a bulldyke.”
I couldn’t believe what I was hearing and told him to just shut it for the time being and I’d give him a full piece of my mind at a more opportune time. I gave it about a week or so before deciding to sit him down, tell him what I thought of his inexcusable behavior, and break it off with him once and for all. Unfortunately, this last rendezvous coincided with my 22nd birthday.
He met me in a coffee shop, and before I could get a word out, he wished me a happy birthday and said he couldn’t wait to give me his present. This ratcheted up the awkward factor exponentially, and I almost felt bad for him for a second. Almost. For a second. I declined and said that I didn’t feel comfortable accepting a gift. His response made my jaw drop.
“Oh, don’t worry. I didn’t spend any money or anything, I was just going to take you back to your apartment and sleep with you.” I just looked at him all slack-jawed, unable to adequately process the overwhelming gall he had just exhibited. So I told him no, never mind, this was never, ever going to work. I’d had enough and wanted nothing more to do with him.
I refrained even from telling him off about his behavior since it was a moot point by now. I operated under the impression that I would be seeing and hearing no more of him ever, but a couple of days after my birthday, he called me up. I answered more out of morbid curiosity than anything else, and I’m so, so glad I did.
He called to tell me that he’d hooked up with a male co-worker in the janitor’s closet of the hospital where he worked, and that my refusal to put out for him was what drove him to do it. Suddenly the phobia made so much more sense; a textbook case of “the lady doth protest too much.” Before hanging up, he had one final request.
His words verbatim: “Since we aren’t seeing each other anymore, I guess we’ll have to find other people. So can I borrow your digital camera? I want to take a picture of my cat and send it to this girl I’ve got my eye on.” This series of unfortunate events had been relegated to bemused memory until this past New Years, when I received an unexpected e-mail from him.
In it, he expounded upon all of his theories of why I never wanted to sleep with him. 1) I’m actually gay and don’t know it, 2) I have a secret substance misuse problem, and 3) I have a long history of horrible treatment going all the way back to my early childhood. Wrong on all three counts, bro. Did I respond to this four-year-belated e-mail? No, Sir!!
Methinks I dodged not a mere bullet, but some heavy artillery with that one.
69. The McDate
A couple of years ago, I met a guy in my senior class boat cruise—it’s like a semi-formal prom on a boat. He was from another school, as our senior class was sharing the boat with a few other local schools. He was nice, smart, tall, and generally attractive. We talked for a while and then exchanged numbers. After a couple of weeks had passed, we agreed to meet up.
I had to drive 45 minutes to his house because his parents “wouldn’t let him drive a car.” When I arrived, he had shaved his head and was MUCH thinner than I remembered. I’m not fat, but I prefer my men bigger than me, and this kid was really scrawny. After several awkward hours watching movies, I asked if he wanted to get something to eat. The only place he wanted to go was McDonald’s.
When we got there, he had forgotten his wallet and I had to pay. We ate in awkward silence and then I drove us back to his house. I figured he could redeem himself by being talented in bed. I made the first move and leaned in to kiss him, and within less than a minute of making out he had managed to take off every item of clothing he had on, even his socks.
Meanwhile, I am still fully dressed and really creeped out. I grabbed my phone and pretended to read a text from a friend who needed my help, and I immediately left. He never paid me back for the McDonald’s.
70. Proper Hygiene
We met online. On our first date, she invited me to her house. The house was pretty disgusting; dirty and plenty of trash around. She was remodeling her kitchen so I gave her a pass on it. The next get together was at my house. I think it was our third date, but maybe second. Anyway, we get intimate and I quickly became aware she had not bathed. She was funky, like B.O. funky.
The next day I get a frantic phone call. “I have bugs,” she said. “Bugs?” I replied, “What kind of bugs?” “Lice,” she replied. “Lice! Like upstairs or downstairs,” I asked? “Up,” she said. “I’m outside your house right now and I brought supplies.” So, she comes in with RID, trash bags, cleaning supplies, and four new pillows. She proceeded to bag everything she thought she came in contact with, throws out my pillows, and leaves me with a bottle of RID.
Fortunately, I never got lice. I still keep the RID under my sink as a reminder to be more careful in the future. I never saw or heard from her again and that was fine by me.
71. It’s Serial
I’ve only been on one blind date, a few years ago. It was with the investment banker son of one of my mother’s friends. One of her attempts at finding me a respectable boy from a good family. So that night he calls to ask if I could pick him up instead since his car broke down. I thought, no problem, and asked where he lived.
The guy was staying at a buddy’s place an hour from my house, ugh, but still no problem I thought. So, I get dressed in my cutest little black dress and heels to channel the grace of Audrey Hepburn, and gosh darn it, I think I did well. I pick the guy up and he’s not all bad. A little on the short side but he has a cute face and seems fit.
So, we get to the restaurant and order. He gets a few drinks into him and we have a conversation about jobs/stuff/blah blah but then it arrived at who we admired. His answer chilled me to my core: Patrick Bateman from American Psycho, just, ya know, without the killing and stuff. He said he admired the character and aspired to live that kind of life (without the killing of course).
DING DING DING…the alarm bells were going off in my head. So, trying to change the subject, I mention the frat that he was in (we both went to the same university) and that I knew some of the guys. He then proceeds to tell me that, yeah, all his friends were just vehicles for him to get ahead in life and that he didn’t really like any of them. Okay.
Then comes the check. He forgot his wallet. So, I paid. Just awesome. By now I was just looking for this night to be done with, but no. Things had to get more fun. On the way back to the garage we pass by an alley and he leans in and whispers into my ear and says, “You’re really hot and I want to screw you behind that pile of garbage,” and he LICKS MY EAR!
WAaaaaaaah blashhldflka Do Not Want! I told him the night is over, gave him some money, and said that he could take public transportation home. I then called my friends and went out to a bar to drink the experience away. Needless to say, I was jumpy for a few days, expecting an ax to come out from a corner at any moment.
72. Planning for the Future
I was really young, probably about 15 years old or so. I was boy-crazy. I had a crush on every guy who even remotely expressed an interest in me. That being said, this one guy…there are no words to describe this guy. His name was Jesse. We met through a mutual friend and, while he wasn’t exactly my type, he told me he thought I was pretty. I wanted to give him a chance—HUGE mistake.
A couple weeks later, we decided to meet up at the mall for our first official date. He was very sweet. We were holding hands. You know, typical teenage stuff. But then he got weird. VERY weird. We’re sitting on this bench, when he turns to me and stares at me right in the eyes before saying, “Wow, when I look at you and I look into your eyes, I feel like I’m looking into your soul.”
I’m fifteen and desperate for an epic love story at this point, so I just smile and let him continue. He goes on to say, “I know this seems soon but…I think you might be my soulmate. I can’t wait until the day we can get married, have babies, and live together. We’re going to have such an amazing life together!”
So let me recap. I’m fifteen years old, I’m on a FIRST DATE, and my date just essentially proposed to me. I got the heck out of there as fast as I could and never talked to him again.
73. Who Wants to Be a Loser?
I once was a “Phone a Friend” for a guy I knew who was on the game show Who Wants To Be A Millionaire. He asked me out on live TV before the question. I said yes, because who would turn down a guy who asked you out on TV? I got the answer wrong and he lost the game because of it. Nevertheless, I still had to go to dinner with him after that.
It was by far the most awkward and worst date ever.
74. Plot Twist
In college, I once went out for a going-away party for a friend. There, I met some girl that a bunch of my friends knew. We got pretty wasted and had a lot of fun. Did shots. Danced. Did shots. Sang karaoke. Did shots. Chatted on the patio. Did shots. Went back to the patio. Drank a bunch. Did more shots. Really liked each other.
So, we exchanged numbers before leaving and said we’d go out sometime next week. Now, 20 minutes after leaving, I literally passed out and landed on my face because I was so freakin’ trashed. So I was in prime condition this night. This girl knew I liked to party as only college kids can (which kind of horrifies me in hindsight—how did I survive?!).
So, next week comes and we line up a date. Since we still didn’t know each other super well, we decided we would go to that same bar where a bunch of our mutual friends would be. We sit with them on the patio and chat. She’s cute. But, that’s all she has going for her. Over the course of the evening, I find out that we are absolute polar opposites in every way imaginable.
Her dad is a preacher and she’s very religious. I’m not. She doesn’t like art. I do. She’s waiting for marriage. I’m not. She doesn’t like fishing. I do. She thinks hunting is cruel and that the outdoors are icky. I don’t. I’m also getting one-word answers to everything I ask. She keeps saying she doesn’t like anything I talk about, while she doesn’t even try to make conversation in return.
It’s so awkward that our mutual friends start bailing, shifting further and further away from us, until there are only three of us left in our section and everyone else is on the other side of the patio. After about 45 minutes, I decide that I’m going to need at least about eight more drinks to make it through this night. I ask if she wants another drink. She says yes and I go inside to the bar.
While I’m waiting to be served, I spontaneously say to myself, “Screw this!” I leave. I bail right out the back door. I don’t even care. I don’t say goodbye, I just leave and delete her number from my phone on the way out. I stagger over to a friend’s house, explain that I was just on the worst date ever, and proceed to get blackout with him. It wasn’t until a week later that I learned what really happened.
Three days later, a mutual friend who we’ll call Kevin says, “Man, that date was pretty brutal! But it wasn’t right how she treated you.” “I know man, right?” “Yeah. I can’t believe you went to get her another drink, and she left before you got back! That was really rude!” Yes, that’s right. This date went so poorly that we both bailed without telling the other person—and neither one of us ever tried to contact the other one again, either.
75. Not Worth the Wait
My worst date was when the guy was more than three hours late. He was texting me telling me that he was 20 minutes away for two of those hours. As soon as he arrived, he tried to tell me to leave the part of the venue I had already paid for so that we could go where he wanted instead. He then tried to start a fight with a friend who I happened to run into and called my aunt a bunch of inappropriate names.
I just walked away from him after that last one, and we never spoke again.
76. Sushi Doesn’t Pay for Itself
I met a guy during college through some friends. He was good-looking, charismatic, and funny. After chatting the night away at a party, he asked me out on a real date. He picks me up in his nice car, but then immediately proceeds to take a phone call. He apologizes profusely, but says he “has to take care of something real quick.”
He drives back to his house, runs inside, and then tells me he needs to swing by a friend’s place. We pull up to this run-down house in a crummy part of town. He pulls out a baggie and a stiff magazine. He then begins weighing out an illicit substance on his lap. He then asks if I want to come in with him. I say no. He runs inside, comes back out, and then apologizes again.
We then proceed to get sushi.
77. Sleep Tight
My worst date was with a guy who had recently been broken up with. We were already friends, so we just went to his house to watch a movie and play some video games. Right off the bat, he lays on the couch and goes on his phone. I have nowhere to sit and end up on the floor. He then opens his ex’s Facebook page and proceeds to show me pictures of her.
When he was done doing that, he fell asleep. I didn’t have a car at the time, so I called a ride and played his video games while I waited. We did not have a second date.
78. Sounds Like Someone Is Chicken!
I went out with a girl on one date and it wasn’t too bad. On the second date, we got chicken wings. She got really messy into them, sucking on the bones and slurping the juices off her fingers really loudly. When we were done, she did not wash her hands. Not even a little lemony hand wipe. Nevertheless, throughout the night, she kept reaching out to touch my face—but that’s not even the worst part.
Not in a gentle caress or anything like that. Her hand would just shoot out and pinch my cheek or grab my nose. Her hands left little sticky marks all over my face. I started to flinch whenever she moved. Finally, later in the night, she went to the bathroom at some place we were at. I thought she would finally wash her hands, but when she came out she grabbed my hand and hers was still sticky.
79. Home Sweet Home
Many years back, I met a really cute guy at the local handball courts. We exchanged information and decided to hang out the next day. I got all gussied up and he picked me up in the same clothing he had been wearing at the park. That was a red flag right there, but I decided to give him the benefit of the doubt. Maybe he had many pairs of the same sweats? Guys always have lots of white tee shirts, right?
So, we started driving and I asked him what the plan was. You know, like where we were going to go. He tells me that he is kind of low on cash right now, but thought it would be fun if we went back to his place and watched some movies. See, now I know what that means, but as a 16, 17, or 18-year-old—which I was, I can’t quite remember—I thought, “Oh alright, he is older. Maybe he just had to pay rent or something.”
As I looked into his big green eyes. I half-heartedly agreed with his suggestion and we headed over to his place. I walk in and he begins to tell me that he lives with his mom and that his ex-girlfriend had moved out a while back. He takes me up to his room, and I am immediately taken aback. He has pictures all over his bedroom of himself and his ex-girlfriend.
I understand that this is like the third red flag, but I begin to rationalize this by saying to myself, “Aww, he is so heartbroken about his ex-girlfriend that he can’t bear to take the old pictures down! I will heal his heart!” Yeah, I know I’m stupid. Anyway, we start talking as he puts some movie on. He then asks me three questions about myself.
As I begin to answer question number three, he stops me and says, “I have heard and learned enough about you. I really like you and I think it’s time for us to sleep together.” He proceeds to take out his privates, flops it out in front of me, and casually points at it. I immediately get up, grab my bag, and run out of there as fast as I can.
As I look back now and reflect on the whole bizarre experience, I know that it was a stupid move for me to have gone back to this sketchy guy’s place right after meeting him for the first time. I also realize that many terrible things could have happened to me, but teenagers are stupid. I’m just glad that I am alive to tell the tale and share it as a warning to others.
80. That’s a Pass (Out)
I once had a girl beg me to take her out. I can’t drive, so she had to pick me up and we went to this restaurant on the other side of town. Everything seemed to be going fine. I had her laughing and was telling her a bunch of interesting stories. She had my attention the entire time as well. She was far from boring. Then, just when I finished eating, I suddenly had a terrible feeling.
I started to get light-headed. This is very rare for me, but it had happened before on occasion and I knew what was going to happen next. Before I could warn her, I passed out at the table. I fell to the floor. When I came to, she was gone and the owner of the restaurant was hassling me to pay the bill. I paid the bill and walked the 11 miles home alone.
I tried calling everyone I knew, but no one was answering their phones. There’s no public transportation in our area either. I ran into her a week later. Curious as to what her excuse would be, I asked where she got off to that night. She called me a freak and asked me to go crawl under a rock and disappear. That was pretty much the last straw for me. I gave up on finding someone to be with.
81. Leave Them Wanting More
I was on a dating site for a while and agreed to meet a guy for drinks after we emailed back and forth. I should have seen the red flags. He was a lawyer, well-educated, seemingly honest, claimed to be a good-looking guy…but he posted a deceptive photo of himself. I barely recognized him when I saw him. But he was just getting started.
He refused to tell me where he worked, or his last name, explained his phone number is unlisted due to his profession. THEN he proceeds to go through all of the photos on my phone when I tried to show him just one. I got the most expensive drink I could find, chugged it, then got out of there as fast as I could carry myself.
82. You Dog, You
I met a girl via Facebook, and we met up at a coffee shop. I don’t even drink coffee, it’s just a cliché spot in the dating routine. ANYWAY. She grabs a coffee, and we start talking. Things go really well. She offers to drive me home after two hours of talking. Then she says “Before we leave, I need to tell you…”Oh. My. God.
She said she’ll be the perfect girlfriend, meet my parents, be the goody-good girlfriend. But two nights a week, she wants me in a kennel at the foot of her bed. She whipped out her phone and showed me pictures. She went into great detail about the things she “needs” from me. She said I’d be perfect for what she wants, blah blah blah.
I tried to be nice and not flip the table and run. I let her down, knowing it was all lots of fun and I really appreciate her being upfront about all that. There are places to go online and seek out people who are into that sort of thing, but sadly I couldn’t do it.
83. Pop Quiz
My housemate told me that one of his friends used to ask girls on the first date if they could name three brands of printer. He would then judge them not on their answer, but how they answered. If they answered quickly and rattled off three “makes,” then they were too geeky. If they said “I don’t know any,” then they weren’t willing to play along.
But, if they managed to get three but were more hesitant over their answers, then they were a good date. He…did not go on many second dates.
Homecoming formal my junior year. My first dance ever, my date picks me up 30 minutes late, and realizes he isn’t wearing a tie or appropriate shoes. We stop at the store, and he steals a tie and some shoes—because apparently he really felt like he was “sticking it to the man.” He then forgets that he never made dinner reservations, so we end up eating a $50 meal. He got steak, I got a salad.
Next, he forgets his credit card and I end up having to pay for both our meals. Oh, but it gets worse. He tells me he just took a pill, ends up freaking out at the dance, leaves me by myself, and I end up having to call a cab home. Did I mention he sat in front of me in two classes so I had to look at the back of this loser’s head for the rest of the year?
85. Hot Metal
First, his dog peed on me. He then sat across the room when watching TV even though I was on a huge couch all by my lonely self. He took me into his room and just when I thought it was going to get hot, he showed me HOURS of all the metal he’d composed. And then he showed me the organ he had made, and played like 25+ minutes of ORGAN for me on his HOMEMADE ORGAN.
Right before I left, he told me he wasn’t physically attracted to me—and then his dog humped me. At least someone was.
86. The Pig Roast
I went out with this one guy and it seemed to be going alright. Nothing really screamed crazy. We went bowling first then went out for dinner. During dinner, he starts talking about his sister’s stag and doe that had been the weekend before. It was a pig roast. Long story short, the guy who was supposed to cook the pig couldn’t, so this guy stepped in to help his sister out.
After the pig roast, him and some friends went back to clean up, which meant getting rid of the pig. What happened next was utterly horrifying. He then began describing to me in vivid detail how they had ripped the pig’s carcass apart, pulled its spine out, ripped its face off and wore it like a mask. I’m sitting there absolutely disgusted—I’m a huge animal lover.
I repeatedly told him to stop, but he was laughing and thought I was joking. He then pulled out his phone and wanted to show me pictures. I actually had to raise my voice for him to realize I seriously didn’t want to see pictures of him and his friends wearing a dead pigs face like a mask over dinner. We did not go out a second time.
87. An Explosive Ending
In college, at the beginning of freshman year, a friend and I took a couple of girls out to some parties. These girls seemed to be really into us, and we were getting hammered so things looked great. At one point, we’re passing around a bottle of vodka, taking swigs. After I don’t know, the sixth or seventh swig in about five minutes, it happens.
I projectile vomit on both the women. Before anyone really knows what happened, I turn around, beeline it for the door, and walk back to the other side of campus without my shirt on. I had to take it off because it was covered in puke; a lot of people taunted me on the way about it. When I got back, my roommate and I played Guitar Hero for a bit, and then I passed out. Good times.
88. Well Prepared
I’d met a girl at a bar at university and we’d exchanged numbers and arranged a meet-up. It was pretty obvious why, too. It turned out that she lived a train ride away from me, so I strolled down to the train station, needing both condoms and a pee. Walking past the university Health Services office, I decided to kill two birds with one stone and take a pee as well as grab some free condoms. Everyone wins.
So, I walk into the toilets and hey, presto, a big sign saying “FREE CONDOMS AVAILABLE HERE,” with a bowl full of silver bags below the sign. I pick one up, take a pee and get out of there. Skip forward to the meeting—the girl and I go back to her halls so I can drop my bags off. She’s the playful sort, and as I’m lying on her bed she starts going through my stuff, being all “I wonder what you’ve brought me” etc.
I don’t mind, until I realize that she might find the bag of condoms. Even though it’s pretty obvious I’m there to hook up with her, we hadn’t actually explicitly talked about it, just heavily implied it. So, I’m lying there frantically trying to come up with a smooth way to pass off the bag full of condoms without sounding like an idiot.
She finds the bag, and pulls it out with a confused look on her face and says, “What’s this?” “Uh… I thought I might need it?” is what I came up with. I guess I hadn’t looked closely at what I was grabbing. She looks confused, opens the bag, and her confusion turns into a mix of outrage, offence, and revulsion…as she pulls out a chlamydia testing kit.
89. All She Does is Whine, Whine, Whine
I met a girl online and we talked maybe three times over the course of a couple of weeks. Then one night out of the blue she texts and asks if she should come over with a bottle…I say sure, since she seemed pretty cool. She turns up half an hour later with an open bottle she has half emptied already. She finishes that off within 10 minutes and I open another bottle, which is gone in another half an hour.
She passes out in my bed, waking up occasionally, trying to kiss me. She then pees in my bed and doesn’t wake up for three hours. I played PlayStation.
90. Parallel Lives
3-4 months ago, I was talking to a girl on OkCupid. Things were going pretty well and we decided to get together. I was on a budget because I was saving to move out of the country, so I suggested a local Thai place which had $0.25 cent drinks with an entrée, figuring the food was pretty decent and the cheap drinks wouldn’t hurt.
I offered to pick her up, but she declined, which is completely respectable. The night of the date, I’m running about five minutes late and feeling a bit rushed when I get a call from her. Even though I gave her an exact address in an easy to find place in town, she’s having trouble getting there. She ends up calling me back 6-7 times in the next 45 minutes as she tries to find her way there, no advice I could give was helping this girl.
By this point, I’ve already been there 30+ minutes and am about three-quarters of the way through my first drink. Red flags about how incompetent this girl must be are going crazy, but I’m already on the ride. The final time she calls me she says, “Hey, is there parking lot?” to which I reply, “No, it’s all street parking, but there were a lot of open spots when I parked.” She then replies, “I don’t know how to parallel park.” Mind you this is a city, parallel parking is a way of life.
I’m pretty dumbfounded that she doesn’t possess this skill. This is already a nightmare in my mind, and as I sit there pondering how to solve it, she asks if I would mind coming out to park her car. I agree and start walking outside, being a bit embarrassed at having to explain that I’ll be right back to the hostess.
I walk outside and a few minutes later she pulls up. First of all, this girl was not as advertised. I got Myspace-angled hard. I’m not someone who needs the perfect girl, but I’m telling you this was out of control. I climb into the driver’s seat and the first thing I say is how weird it is. I tell her I haven’t driven anything but a manual in three years and her automatic feels very strange.
I slowly accelerate and head down the block. Part of the way down I see an open spot. I let off the gas and instinctively go to push in the clutch. Instead, I stomped the brake. Hard. This girl had quite a lot of mass and wasn’t wearing a seatbelt. Any physics student knows what happened next. Her head flew forward and nailed the dashboard.
I start apologizing like crazy, and luckily she wasn’t hurt. We spent the next hour having a really awkward dinner and then parted ways. No, we didn’t call each other.
91. Heartbreak Hotel
I was seeing this girl on and off. She told me that she had a hotel room for some cheerleading event she was coaching at the time and asked if I wanted to come over and keep her company. Her hotel was in King Of Prussia, Pennsylvania. I live in New Jersey. Offer of a fun, private hotel get together, but a bit of a drive? Sure, I’m in!
So I drive the couple hours out there to meet her, meet her in the hotel lobby, and go up to the room with her. To my surprise, her dad is in the room…because it turned out this was a cheerleading competition for her little sister. In other words, her entire family was there…
Her father got called unexpectedly into work (he was a firefighter), so he was leaving her the hotel room for the night. He was carrying his overnight bag out as I was carrying mine in. It was unbelievably obvious to him as to what was about to go down, making it extremely awkward for me.
I have never felt so uncomfortable in all my life.
92. Good Things Come to Those Who Wait
I once went out with this guy who I met on a dating site. We were at a restaurant and he spoke very loudly the whole time. It was as if he didn’t have any volume control whatsoever. He was also very arrogant, so I didn’t even want to talk with him anymore after a few minutes. To top it all off, he looked nothing like his online pictures.
On the upside, though, the waiter we had ended up slipping his number to me. He could clearly tell it was a bad first date, and he took me on a much better date a few days later.
93. A Funny Thing Happened on the Way Back Home
I had a very disappointing date in high school. It was the dead of winter. Like -40 degrees. We had gone to a movie, and the whole thing was really awkward. She didn’t really seem to want to be there and was very detached. After the movie and the bus trip home, she admitted that the only reason she had even agreed to the date with me was because my friend had turned her down a few days earlier.
I wasn’t aware of that at the time. It was a pretty big letdown and the whole thing felt like a waste of time at that point. But I figured “Whatever, I’ll just head home and find something else to spend time on. I’ll get over it eventually.” I got off the bus and just wanted to get home as soon as possible. At the bus stop, there was a thigh-high railing around the front of the nearby parking lot. Instead of walking around it, I decided to step onto and then over it.
The second I stepped onto it, I realized it was coated in ice. I flipped through the air and lost everything in my pockets. I ripped my pants from the bottom all the way to the zipper. I then came down hard right onto the railing with my shin, fracturing it. It was still freezing cold out. I couldn’t just lay there until help arrived. So, I fished around in the snow, grabbed my stuff, and staggered home.
94. Riding Off into the Sunset
My first-ever online date was with a girl who was into biking. I suggested that she pick me up and we ride to her favorite restaurant. She pulls up to my house, weighing 100 lbs more than her pics and wearing a skin-tight bright red Lance Armstrong bike suit with all the accessories. She then proceeds to almost get us killed while riding in traffic at least five times on the short two-mile trip.
She also sweated like mad through the suit. As if that wasn’t enough already, the restaurant she had chosen turned out to suck!
95. A Rollercoaster Of Emotions
A few years back, I was just getting out of a long relationship. My boss’s sister decided to set me up with one of her co-workers. Let’s call her Susan. So she gives me Susan’s number, and I decided to give her a ring. She sounds all right on the phone and is very open and flirtatious. I ask her if she wants to go and get some coffee, to which she says yes.
We agree to meet at her parents’ house in a couple of days and then head out to get coffee from there. In the two days between making our plans and the actual date, she starts sending me affectionate text messages that always address me as, “sweetie” or “honey.” I figure that if anything, she is just a really affectionate person and try not to read too far into it. Eventually, the time of our meeting arrives and I go to pick her up.
She is a knock out! Blonde with a full tan, and nice figure. I am kind of a schlub, and so I can’t believe my luck. As we are getting ready to go, she says that she would rather take her car since it would make her feel more comfortable. Being a good guy, I can see her reasoning and acquiesce. This would later come back to haunt me.
So we start driving when she informs me, “I’m not really in the mood for coffee. Let’s get some drinks!” Now, I am not a drinker. However, at this point, I am going along for the ride and agree. 15 minutes later finds us in a brewery sports bar. I decide to stick to soda, while Susan decides to take things slow by ordering straight shots to get things started.
Pretty soon, though, we are hitting it off really well. I tell her about growing up with an illness, and she relates how she got over ovarian cancer. We find out that we share some common interests in movie tastes and hobbies. Things are going fine until she has her third drink… “Oh, GOD!” she hisses while ducking down. “What?” I ask, confused.
“You see that guy over there? In the booth with that girl in the blue dress?” I see the one she means. “Well,” she continues, “I sorta used to sleep with him.” I am taken aback by her blunt honesty. She then goes on to explain how she lets people use her as a means to cover for insecurities. Next thing you know, she is opening up to me like I am Oprah.
All about how she likes to cut herself and how she has attempted to take her own life in the past. Then she is reaching across the bar to take my hands. She looks in my eyes and says, “You know, I feel a real connection to you…” Then her phone goes off. She checks it and informs me that it is a text from her ex-boyfriend. He is in the Marines and is shipping out the next day.
Apparently, he is coming over to meet up with us so she can say goodbye. By this time, I have realized that I don’t want to be anywhere near here. I also realize that we took her car, and she is now many drinks in. And to make it even worse, we are in a neighborhood that I have little knowledge off… I’m trapped. Pretty soon, the ex-boyfriend shows up.
Big beefcake guy in his uniform. She starts to flirt heavily with him and ignore me. She is on her sixth or seventh drink. It soon becomes known that the ex-boyfriend is also in the business of recruitment. “You ever think of signing up?” he asks me as he takes in my nerdy frame. “Nope,” I answer, “I’ve got medical dispensation.” “Oh yeah?” he asks, “What’ve you got?”
Susan starts to answer for me, “Oooh, he’s got cystic fib…” I cut her off, “I’m allergic to bullets.” He doesn’t look impressed. Soon Susan and Beefy Marine go outside and leave me to watch the table. I just want to get out of there. At this point, I should mention that Susan’s day job is as a behavioral therapist for autistic kids.
My boss’s sister is her supervisor, and I happen to know that Susan is expected to be at work at 6 AM. I know this because Susan told me. By this time it is creeping past 12. After they come back, I decide it is time to try and get this girl’s keys from her and get back to my car. But not before she can introduce me to three more exes, and one guy who she practically starts making out with in front of me.
I ask her for her keys, and say that it is time to go. “No! No one drives my car but me.” Dear God. I weigh my options, and for some reason decide that “it can’t be more than five or six blocks back to her place, she might be fine to drive that far, and if all else fails I’ll tuck and roll out of the moving car…” I get her to her car and we start heading back.
Suddenly, she looks up in her rearview mirror and screams, “THE FUZZ!” before randomly swerving down a side street. She starts zigging and zagging at high speed through residential neighborhoods. I look behind us only to see…no car. Finally, she decides that “Oh, we lost them” and heads back to her place for real this time.
Now, you think the story would end here…But there is more crazy to come. As I am trying to make my getaway, she asks me to drive her back to the bar. “If you don’t, I will drive back loaded. I’ll then drive home even more loaded, and probably get in a crash and die.” She tells me. Fine. Screw it. Whatever. I tell her I will give her a ride.
Before we can get in my car, however, she informs me that she has to pee. I figure that she will go in the house…I figured wrong. This chick hikes up her skirt, pulls her thong aside, squats down, and proceeds to pee on the sidewalk right in front of me. I immediately spin around and avert my eyes and mumble an apology.
“It’s ok.” she says, “you can watch. I don’t mind. In fact I kind of like it.” I decline her offer. Finally, I get her in the car and start heading back to the bar. On the way back, she grabs my hand and slams it into her crotch. She starts telling me how she feels a real connection to me, “I don’t want to say ‘soulmates,’ but have you ever seen the movie, The Notebook?”
I tell her I haven’t, “Oh, well It’s kind of like that.” The whole time as she is saying this, and my hand is in her crotch, all I can think is, EEEEWWW, she drip-dried! Then she says what is maybe the icing on the cake, “The last time I felt this way about someone and they didn’t feel the same way…” she lets out a little laugh, “I tried to kill myself.”
That’s it. Get her out of my car! I pull into the parking lot. I pull up to the curb and try to get her out as fast and politely as possible. “Can I kiss you?’ she asks. “No. I would be a little uncomfortable with that.” I tell her. “Well, what about just one on the cheek?” she pleads. I figure, fine, anything to get her out of the car. I lean over and present my cheek…
Only to have her grab my head, and then like the face-hugger from Alien, jam her tongue down my throat. I start to flail around. She finally releases her grip and exits my car. Before she goes, she leans down and says, “I really messed things up tonight. didn’t I? You’ll probably never call me again.” “No.” I lie. I then get the heck out of there.
The next morning at work, I relay this crazy story to my boss, when suddenly I get a call from his sister. Susan didn’t show up for work that morning. She isn’t answering her phone. Her parents say that she didn’t come home either, and everyone wants to know what I did with Susan. Great. Crazy chick goes missing, I was the last person to see her. I’m going behind bars.
Eventually, she turns up claiming that her phone was out of batteries and that she had spent the whole night at the hospital with her grandfather who had a heart attack. I of course know all of this is lies. But whatever, I don’t have to deal with her anymore. She’s out of my life. Or so I thought…That’s when the voicemails began.
Tearful, jarring sobs of, “I sob just sob wanted to say sob ‘hi’ to you…” and, “Hey love, why aren’t you answering my calls?” and my favorite, “What did I do?” Eventually a month later or so, she got the hint and left me alone.
96. Sore Loser
I was in my late 20s teaching SAT test prep and this guy asked me what my SAT score was. It turned out I beat him, and he spent the ENTIRE rest of our dinner trying to trump me at some scholastic endeavor from high school or college. Did I take AP courses? Yes. Did I take Calculus? Yes. Who went to the better college? Me.
Aaah, but he took some programming courses and those are really hard, you know. Dude, I’ve taken programming courses, too. It went on and on and on. The jerk would not let it go. You know, normally as a woman I tend to play down my accomplishments because bragging is bad manners, but that night I was in his face rude about being brilliant. Then he wondered why I didn’t want to go back to his house afterward…
97. Eating For Two
I chatted a girl up online for about a week or so, and things went pretty well, so we decided to meet up. I asked her out for dinner, and said that if things went all right we’d go grab a drink. Let’s just say her photo didn’t match her appearance. Her excuse was that she had a crazy ex who was stalking her, so she used her sister’s photo and name.
HER NAME!!! SHE LIED ABOUT HER NAME! Anyway, come to find out through our “interview” that she was an only child. She didn’t catch her slip up, but I sure did. She rambled on and on and on about stuff I really couldn’t have cared less about. Then came the food. The waitress may as well have brought it out in a trough, as this woman didn’t use her utensils.
Did I mention we were at a steak restaurant? That’s right folks, she picked her steak up and ate it with her hands. Let’s not even get into the potatoes. It was the worst date of my life. I couldn’t eat my meal. I told her I wasn’t feeling well and that I was just going to get my food in a box to go and I’d eat it later if I felt better. Her response: “Would you mind if I ate it?”
She proceeded to devour my dinner as well. The waitress comes over and says “Goodness. When is your due date?” So she says that she is due in two months. First off, I couldn’t believe the waitress asked that, but then I was floored at the girl’s response. Unbelievable. Being the gentleman that I am, I picked up the check because hey, it wasn’t going to pay itself. I kindly said it was “nice to meet you,” got in my car, and went to the bar. Well, she followed me.
She followed me to the bar, and when I got out of my car, she proceeded to berate me over why I was going out instead of going home. Now she’s calling me a liar in the parking lot of the bar I frequent, and my work buddies are starting to roll in. I never heard the end of it. I said to heck with this, got in my car, and drove home.
98. The First Cut Is The Deepest
It was the first date I’d ever been on. I wasn’t the most talkative guy in school, but I rather fancied her so I worked up the courage to ask one day—and to my surprise, she said yes. We were both 15/16 years old at the time. I get a ride to her place from my mom, we pick her up and head over to this restaurant in one of the classier parts of town.
We get dropped off, head in, make light conversation and I find out she’s never been there before. I’d only been there once myself for my birthday, a year or two ago. She asks me to order for her and I do so; two steaks with the trimmings. Anyway, things continue rather pleasantly and our food arrives. We dig in and continue to talk but I notice about 15 minutes in that she’s gone a little cold on me and she hasn’t yet touched her steak. She’s picking off the veg and potatoes around the side, but the steak is untouched.
My natural reaction is that I didn’t ask if she had any dietary restrictions; so, I apologize immediately and ask if she doesn’t eat meat. Her response is so disturbing it’s unforgettable. She says she does eat meat, but: “I’m waiting for you to cut up my food for me!” Apparently, at the age of 15 years old, she’d never once had to eat a slab of meat that wasn’t first cut up for her by either her parents or whomever else she was with at the time.
I was surprised, but I taught her how to cut up her own food—seriously, girl didn’t seem like she’d ever held a knife before—and afterward, we dropped her off at her place in silence. So…thus ended my first date, and last date with her.
Waited for her at the theater for two hours. She shows up loaded. Watched a terrible movie, just whatever was about to start. She took me to a bar afterward. Ended up being a gay bar and she tried to get me to admit I was gay. I flirted with the gay bartender to make the night less awful.
100. Bad Suggestions
My twin brother passed in a car wreck and my family suggested that I should date his girlfriend because…grief, I guess? REAL FREAKIN’ AWKWARD, MOM.