Faint heart may have never won fair lady, but none of these dates are winning anything, either. From clueless attempts at seduction to serious attempts at Catfishing, these people lived through some of the worst “romantic” nights of their lives and survived to tell the tale. Get ready to delete all dating accounts and become forever celibate, because these are genuine dating horror 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. I Spy With My Little Eye
I was at work and a stunningly beautiful woman walked up to me and asked me out. I was in college and she was probably about 25 or 26 years old. It was an amazing date. She was funny and cool and insisted on paying for everything. At the end of our meal, she looked at me and said, “I promised myself I wasn’t going to sleep with you, but I’ve changed my mind.”
Back at her place, things got wild. But something felt off the entire time. She was very particular about positions and what parts of the room we stayed in. She also described everything we were doing in a very loud voice. By the time we were finished, I was creeped out. I knew something was up. On the drive home, I badgered her until she finally admitted that her fiancé had been secretly watching us the whole night.
3. 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. For some reason, I said yes. I soon found out this was a huge mistake.
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. Never did.
4. 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!
5. Pick A Partner
My prom date was horrific. It was a double date with some girl I’d never met, and it turned out we had both just been dumped. I tried to make conversation, but she just wanted to talk about her ex. Well, 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 the guy to come back to her.
6. 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.
7. Knock Em Back And Knock Em Out
I bartended for a decade. For a while, I was at a mid-range Italian restaurant. More than once I saw a first date go awry because one of the two drank too much. The most memorable one was a woman who started downing rum punches. They were at a table, so I couldn’t see them, and I guess the waiter had forgotten his “red light, yellow light” training—I don’t know if they still do that.
After the sixth one, I asked if these were all going to the same person, and he said yes. I was like, oh snap. Sure enough, the girl ended up puking all over my bathroom and locking herself in. When we got the door open she was passed out, and there was puke everywhere, including all over her. No cab would touch her, so the guy ended up taking her home.
He came in a week later and said they were going on another date. I was skeptical. They’ve been married for about 15 years, and are absurdly happy. She avoids the punch now.
8. 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. She suddenly got a text that made her 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.
9. Best To Keep Your Mouth Shut
I once went on a date with a man who had no teeth. We met on a dating website, I had no idea because in all of his photos his mouth was closed. I wasn’t even as bothered about that, as I was about the fact that he kept going on and on about his “best friend,” who was a 15-year-old girl that lived next door to him. It was weird.
How great she was, how much time they spent together, and about how no one, “understood their relationship.” Mind you, he was in his early 30s. I stayed through the whole date, but let him know I wasn’t interested in a second. NOPE.
10. From Weird To Weirder
I had met this girl online, and she was actualy 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, childish 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, then 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, lord help me.
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.
11. Save It For Later
I’ve got a great one. I’m a waiter, and this happened at my former restaurant. There was a reservation for 6:00, a young guy comes in a few minutes early, tells me he’s kind of nervous because it’s a first date and he hasn’t had many before, blah blah blah, kind of sweet really. Anyway, the girl arrives about half-an-hour late and proceeds to get very, very tipsy.
About mid-way through the meal, she answers her phone, takes the call, and starts talking about her date, in front of her date, saying stuff like, “Well, he’s not usually my type, I don’t exactly like him, but I felt like why not,” right in front of him. The young man looks so discouraged, walks up to me, pays his bill, and leaves. He’s a really nice guy, he’s come to the place I work now a few times.
12. The Right Way To Start The Millennium
It was the year 2000. I worked at a takeout restaurant, and a lady came in one night with a younger attractive blonde. After they left, the lady came back in and asked if I would be interested in taking the blonde out. I was told she was a German exchange student. I said sure and gave her my number. A few days later, the blonde called.
Her English was okay, but not to the point where it was super easy to communicate. We made plans to meet near where she was staying, and the older lady was going to drop her off. The plan was to go to a movie and then maybe grab something to eat after before she would call to get picked up when we were done. We met up and headed to the movies.
The car ride there was a bit awkward as she kept repeating herself, but I thought it was simply the language barrier and wrote it off. We got to the movie and she immediately excused herself to go to the bathroom. She came out and we finally took our seats after a long search for two spots next to each other. We wound up having to sit in the first row.
The whole time we were walking around, she kept grabbing onto my arm to seemingly balance herself. I still didn’t think much of it—but soon, the truth would come out. We sat down and, right away, she said she had to go to the bathroom again. I said okay, but she told me that she needed help. Here is where I started to worry. I walked her over to the bathroom and stood outside for what seemed like at least 20 minutes or so. This whole time, I had no idea what in the world was going on.
Finally, some lady came out and asked if I was waiting for someone. When I said yes, she told me that there was a blonde lady laying in one of the stalls. Just great! Not wanting to walk into the women’s bathroom, I went and got a manager who sent a female worker in and then closed the bathroom off. I finally went in to find her sprawled out on the ground with her shoes off.
Her purse had spilled out all over the floor, and she had clearly thrown up. The remnants were in her hair, and everywhere else too. The manager called a life squad after we couldn’t get her up. They showed up, along with the authorities. Fabulous! They, of course, grilled me and didn’t believe me when I had zero explanation as to what the heck was going on.
The squad took her to the emergency room, where I spent the next hour waiting for her to wake up after they pumped her full of fluid. When she finally came to, she told me she had been nervous about going on the date, so she had some vodka. It must have been a massive amount. She called the family she was staying with and arranged for them to come pick her up.
Once I saw that she was okay and had people on the way, I got out of there as fast as I possibly could—never to see or hear from her again.
13. Pick A Good One
When my date complained about the drink selection at a place with over 50 lagers on tap, because they didn’t have a specific one he had, “while doing a peace mission,” which was actually just him taking a vacation and staying on peoples couches that he met off the internet in Central America. He also was super judge-y about my taste in music, food, hobbies, and career.
Too “corporate” and too “mainstream.” He also was just a huge tool bag in general—he didn’t even offer to pick up the bill. Like not even his half, I’m fine with going Dutch. He then took a bunch of my leftovers home. that he didn’t pay for!!! Another time, a guy told me he really liked to snuggle with his mom. He was almost 30 years old. Needless to say, I’ve dated some winners.
14. 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 sloshed 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. Did more shots. Really liked each other at the end of the night.
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 hang out 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.
15. 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.
16. Gone Fishing
I’m a waiter, and there was this young guy eating dinner with—what I thought was—his mother. I noticed that they seemed weirdly uncomfortable, and distant but didn’t think much of it. Turns out the lady was not his mom. He had met her on a dating site and had been VERY clearly catfished. The lady was at least a good 20 years older than him.
When she left the restaurant he stayed behind, and told me about what happened, then asked me out. I politely declined but agreed with him that that was a really weird situation.
17. 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.
18. 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 beat up officers, burned his arm to impress girls, spent significant time in a psych ward, and lost his virginity to an overweight sex worker. 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.
19. 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.”
20. 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 wasn’t over.
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!
21. Hot Date!
Me and my girlfriend sat next to an obvious first date at a Pan-Asian fusion restaurant. She comments that her main course wasn’t quite what she expected, and thought it’d be spicier. He then snaps his fingers above his head, VERY loudly, so half the restaurant turns round to look, and a waitress rolls her eyes and goes over.
He demands that they COOK IT AGAIN AND MAKE IT HOTTER. Next thing, there’s half a dozen Thai waitresses around the table calling him worse than dog waste in Thai—my Thai girlfriend translated—causing a massive scene while his date’s face turns red, and they take her plate away. She then has to sit with no food while he continues eating.
He eventually realizes he’s messed up, and stops eating, but she sarcastically tells him to enjoy his food. They brought her a fresh plate and they eat in silence. First—and I’m sure the last—date.
22. Memory Loss
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. Then she said five words that made my blood run cold. She said: “You don’t remember, do you?” Turns out we had slept together like five years earlier…there was no second date.
23. 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. 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.
24. 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??”
25. 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.
26. 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.
27. 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.” Okaaaaay.
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.
28. 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, 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.
29. A Hair-Raising Story
I have long hair, which I absent-mindedly play with a lot. While on a date with a guy, he noticed that I had this habit and suggested that I try not to do it. The more I did it throughout the evening, the more angry he seemed to get about it. It got to the point where I did it again, and he physically grabbed my wrist quite forcefully before ordering me to stop touching my hair.
30. Toad Be Or Not Toad Be
I once tried using Tinder, despite my ugliness. I somehow matched with a girl who wasn’t too shabby looking. We texted for a few days until we were both free. When the time came for our date, I picked her up. She was very cute, and we went to dinner at a Japanese steakhouse. We had a good time, ordered a few drinks, and she eventually suggested that we go back to my place. Woo!
We stopped by her apartment to get her car and she wanted to grab some new clothes. She then followed me to my house and we made out in my driveway for a few minutes before starting to move towards the house. I was super excited. We got to my front porch and she suddenly screamed “Eew, what’s that??” before pointing to this cute little toad that used to hang out on my porch.
This was his second year hanging around my house and he had become almost like my pet. I explained all this to her and started telling her all about how cool he was and how I enjoyed knocking beetles off my porch light for him to eat and what not. Then, all of a sudden, this night turned into a horror movie. She walked over to him, looked at me, gave me some intense eye contact for a few seconds, and then proceeded to slowly stomp my toad to death.
Now, at this point, I was experiencing several emotions at once—shock, anger, rage. I shouted at her, “Why on earth did you do that??” to which she replied, “I wanted to make you mad so you’d be aggressive in bed.” I was speechless while I tried to process what I had just witnessed. I told her to get the heck off my property.
She flipped out and we started to yell at each other back and forth. After a while, I sprayed her with my hose and she finally left—only to show up again, without a shirt, 20 minutes later on my backyard deck. She had walked back from down the road and pulled about six pickets down from my fence to get into my backyard. The authorities came. She cried her way out of trouble with them and finally left for good.
31. 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.
32. This One Gets Bad Real Fast…
In 2005, I was on OkCupid and met this guy who seemed smart, interesting, and funny. So we chatted a bit online for a few days and then met at a coffee shop. All seemed normal and well, and he seemed like a nice enough guy. A week later, he invited me out for dinner. We had dinner, and it was all normal and fine. Nothing to complain about.
Again, there weren’t exactly fireworks, but I wasn’t put off by him or anything, either. There were some things that now I know are warning signs. He made strange comments that, looking back, were really kinda crazy and woman-hating. For example, he kept making insulting remarks about women in the restaurant. Things like, “She’s dressed like a loser,” “I bet those breasts are fake,” etc.
Anyhow, he sent me a message a few nights later and asked me if I wanted to come over and hang out. I didn’t have any other plans that night and I was bored. He lived about a mile from my apartment, so I walked over to his house. I didn’t have plans to sleep with him and the extent of the physicality of our relationship up to that point had just been a couple of hugs.
When I arrived, it was clear to me that he had been drinking. He wasn’t fully wasted, but he was certainly on his way there. He offered me a drink and I declined. We hung out, listened to music, and even played some music together since he was a musician and I like to tinker. We also talked a whole lot and everything was generally going okay.
Then, he starts telling me crazy stories about his life. He told me a bunch of personal stuff about how he had been mistreated by a relative as a child, how his best friend in high school had lost his life in a car accident with him in the car, how his mother was schizophrenic, etc. Then, he starts talking about how lonely and sad he was and how long it had been since he had met a woman he liked.
He told me how much he liked me, how attractive he thought I was, and how much he wanted to sleep with me. We had cuddled and kissed a bit earlier in the night, but I was not interested in going all the way with this dude right then, especially knowing that he was intoxicated and acting a bit strange. Nevertheless, he started coming on to me really strongly and grabbing at me.
I moved away and tried to tell him I wasn’t interested when he literally started begging me to sleep with him. He was whining and pleading and begging, telling me he’d do anything I wanted. I really had no idea how to react. This had never happened to me before. I felt really uncomfortable and should have left right then, but I felt bad for him.
He was clearly damaged and intoxicated. I tried to tell him that I liked him but didn’t want to sleep together right then. I made some comment about how I needed to leave soon, when he suddenly grabbed me by the waist and pushed me down on the ground. I had been sitting on a couch up till that point. He reached down and tried to pull off my pants.
I ran out of his house as fast as I could and sprinted all the way back home. It was the weirdest experience of my life, man. He never contacted me again; but a couple of years later, I ran into him at a bookstore. He looked at me and started walking towards me, like he was going to talk to me. I immediately power walked out of there.
33. Not What She Signed Up For
I went on a date with my then-wife. After we ordered food, she said, “This isn’t really what I wanted.” I thought she meant the restaurant. Nope. She slid her wedding ring across the table and left. Her mom was waiting outside for her. I got home and the apartment was clear of all her things except the divorce papers.
34. Sounds Like Someone Is Chicken!
We got chicken wings on our date. 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 it got so much worse than that.
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.
35. Missing Information
When I was a host at a restaurant, I sat a couple in their mid-40s at the bar. Their server was my roommate, and she comes up to me, saying how weird they were, same-siding, making out at the table, etc. A few minutes later, an angry-looking man comes storming into the restaurant, and stands at the host stand just looking around.
I asked him if he needs a table, and he gives me a glare, and then marches over to the couple in the bar and sits down opposite of them, the woman looks horrified. The angry guy is whisper-yelling at the woman, all I could make out was that she was on a date with a man she works with and the angry guy was her husband, who found out through another friend.
Now, I’m just standing at the host stand, five feet away, watching all this go down. I grab another server walking past me and tell them what’s going on. The husband at the bar starts getting louder, so my roommate gets the biggest cook we had, and had him go to the table, and tell them to leave. The woman and husband leave, leaving the other man there just looking confused.
He sits there for a few minutes, just kind of staring down at all the uneaten food, before getting up, and coming to the host stand to ask for his bill. I go get my roommate so she can print the check, when I come back, he pays and just says, “I’m sorry for the disturbance, I didn’t know she was married,” and leaves. I felt so bad for the poor guy. He seemed very into her up until her husband showed up.
36. 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.
37. 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.
38. 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!”
39. 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 the bedroom 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 you-know-what. 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.
40. 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, ever 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!
41. Father’s Day
It was grade 11, and I had just moved to a new town. I quickly became attracted to this one girl and would’ve given anything for a date with her. We got paired up to be partners in our “Food and Fabrics” class, and I totally pulled out all the stops. I was doing whatever it took to get a date with this girl. It was all I cared about.
In the class, there were a couple of projects where you would have to sew a pillowcase or a pair of pajamas. My family didn’t have a sewing machine, so we would do the projects at her house. Upon these visits, I began to question how badly I wanted this girl. She lived in what appeared to be a wood cabin, and her father seemed legitimately insane.
The walls were lined with animal skulls, the guy was a devoted hunter. He had bear-skin rugs and antlers all over the place. He would always walk around with his shirt off, drinking a Budweiser, chewing snuff, carrying a deadly weapon. He never spoke a word to me. The whole experience of being in that house just felt extremely weird.
By this time, I was starting to gain some friendships in the school, and one of the guys I met named Neil noticed that I’d taken a liking to her. He then asked me if I’d heard about her parents—and let me know the jaw-dropping truth about them. He proceeded to tell me that her father had taken her mother’s life and gotten away with it. Her body was found in the middle of town, pumped by a couple of rounds from a weapon exactly like his.
He got off on the charges due to a lack of proof, and the girl had to live with him because he was her last living relative. At this point, I was like “What in the world???” The story made no sense, and I wasn’t about to believe it. It definitely kinda rattled me, though. But there was no way that I was going to bring it up to her.
Anyways, a little time passes, and I ask her out. I go to her place to grab her, and she’s gorgeous. Her dad makes a comment about, “You know what’ll happen to you if you touch her,” and suddenly the story is the only thing I can think about. We went skating, then to a movie, but I was terrified the whole time. I just couldn’t get the thought out of my head that her dad was going to attack me when we got back to her place.
So, after a sub-par date, I start the long drive back to her place. We get to the end of her driveway and she gets me to park and turn off the lights. She wants a kiss. At this point, I forget all about her dad. I lean over, and put some moves on. After a few minutes, we stop and I turn the lights back on. There’s blood in the snow at the end of the driveway.
I wanted to say something when I noticed this, but I didn’t want to sound like a scaredy-cat. Her dad was a hunter, right? I’m sure there’s a logical explanation. I put the car in drive, and start the winding trek down her driveway. The trail of blood seems to be getting thicker, and I’m getting more freaked out with every passing second. She still says nothing, as she’s fixing her hair in her mirror.
I keep driving. More blood. I turn the last corner of her driveway, and see my headlights shift from the trees to her father. Standing in the middle of the driveway. Covered in blood. Blood all around him. Huge knife in his hand. And what appeared to be a naked human body lying at his feet. I start hyperventilating. Suddenly, I’m crying, and don’t know why.
I pee my pants right in front of her. Her dad takes me to the hospital. Turns out I have had mild-asthma for my entire life and had a panic attack that triggered it. Apparently, the dad had found a bear at the end of the driveway, shot it, dragged it down the driveway, and skinned it before we got back. But that’s not even the craziest part—the girl’s mother was still alive and lived just a few blocks away! That guy Neil totally wound me up.
Once we cleared everything up, everything somehow turned out okay. This happened a little over three years ago and I’m still with the girl. Her dad makes fun of me all the time, except we’ve gone on hunting trips together and I’m pretty sure he’s secretly a fan. Neil was just a jealous ex with a wild imagination. Her parents had simply split up. And her mom turned out to be pretty awesome too.
42. 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—until the end. 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!
43. In The Driver’s Seat
A boy asked me out on a date and said he would plan it. I thought that was great! A man who takes initiative, what a change! He then calls me 45 minutes before we are expected to meet up, says his car isn’t working, and asks if I can come pick him up instead. I go over, and he invites me in. His apartment is a total pigsty, with comic books literally floor to ceiling like something off of a hoarders show.
He tells me that the place where he wants to eat dinner is a steakhouse over an hour away. I drive us, and he talks the entire way about his adult comic book collection. We eventually get to the place and sit down for our meal. He orders steak and lobster, while I order salad. At the end, the check comes, and he claims he lost his wallet.
I pay, but think to myself that he darn well didn’t lose his wallet because he would have at least checked his pockets before making the claim. I start driving him home. I’m staying completely silent because I now view this guy as a clown. Then, all of a sudden, I hear a sound. I look over and discover that he has pulled his pants down. I immediately pull over, kick him out of the car, and leave him out on the side of the road 30 minutes from town. Screw you, Scott…
44. Up And Left
I work at a pretty high-end steak house. I got sat with a table of two, and when I greeted them, I assumed they were a couple. It took them quite a while to order their food—I had to go back quite a few times and ask if they were ready. After an hour of them talking, ordering cocktails, and looking at the menu, they finally ordered.
The woman ordered a filet mignon, and the guy ordered our most expensive steak. Right before their food came out, I saw the guy get up, and walk towards the bathroom. My coworkers ran their food to their table, and the woman sat there with all the food in front of her. I thought he was coming back soon, but around 20 minutes went by, and there was no sign of him.
My manager walked over to me, and asked me what was up with them, I said the guy was in the bathroom. My manager went and asked her if she wanted us to keep the food under the warmer. She said yes, and the food was under the warmer for maybe an hour while she sat at the table alone. I walked over to her and asked if everything was alright.
She immediately broke down, said it was their first date, and that they met on Tinder. Apparently, she told him that a steakhouse was a little much for a first date, and suggested coffee instead, but he said no. As they were sitting there talking, he looked at his phone and said, “my daughter has an emergency,” and he quickly got up and left.
She was texting him after, and he never replied. This girl bawled to me for 20 minutes, repeatedly saying, “what’s wrong with me?” and I had to reassure her he doesn’t know what he’s missing, blah blah. I went over to my manager and asked what we should do about the check. He said he was stuck, because it was a $250 tab, and that’s too much to just not have her pay.
After a few minutes of convincing him, I got him to take everything off the bill. I boxed up all the food (including his steak and sides), brought it over to her, and told her to enjoy her night. She stopped crying, thanked me, and left. After writing this, I’m now wondering if they swindled me.
45. A Funny Thing Happened
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.
46. 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? Spoiler: This doesn’t end well.
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 teenager—which I was—I thought, “Oh, he’s 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 nether region, 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.
47. Prom Heist
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.
48. 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. This was the beginning of my nightmare.
The puck conveniently went flying to my right, nailing my friend’s date square in the forehead. Annoying giggles quickly turned into painful 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.
49. Photo Finish
I was at my new boyfriend’s house for the first time when I noticed a certain photo on the wall. I said “What? We have that same photo at home! Why do you have a photo of my great-grandmother on your wall?” Looking at me confused, he said “Because she is my great-grandmother!” I will never forget the shudder I felt when we realized what this meant…
50. 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!
51. Scarred For Life
I once rode my bike for 17 miles on New Year’s Eve for a date, only to discover that my girlfriend already had other plans, and they didn’t include me. I turned around. On the ride back home, I crashed and left a few large holes in my face from which I still have scars, five years later. I think it’s pretty safe to say that this was my worst date ever.
52. 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. There’s a funny epilogue to this, 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. Honestly, it really is a small world after all!
53. Down Under And Dirty
I’m Australian. My online dating profile said that I was Australian. I very clearly have an Australian accent. There is literally no way for my date to have not realized that I was Australian. Nevertheless, the very first thing that came out of my date’s mouth when we met up was, “I hate Australians.” That date didn’t last very long…
54. A Previous Engagement
I once met up with a woman for a blind date and a little bit into our conversation, she suddenly got excited and asked me to congratulate her. When I asked why, her reply made me go white. She said, “I just got engaged last weekend!” Ummm, what??? Then what on earth are you here with me for?? I swear, there are some people whose brains I will just never understand…
55. All In A Day’s Work
I once went out with a guy I had met at a Christian youth group in high school. He took me to the movies, complained about how in love with my best friend he was, and then awkwardly tried to kiss me. He was a total weirdo. He stopped talking to me after that, but started creepily hanging near my friends all the time until he graduated. So that was fun!
56. Three’s A Scene
I’m a server, and one time I had two women arrive together to my restaurant. I figured they were just out for drinks. They requested a special table with a window looking out to the bar. Whatever. They’re seated there, and I serve them drinks when suddenly one of them stands up, and runs around to the bar side.
Apparently, she and her friend were scoping out her husband and caught him at the bar with another woman. She starts yelling and cursing at them, and the husband and “other woman” leave. She followed them into the parking lot shouting, “YOU FREAKING LIAR.” I got a bad tip from the two women, but it was worth the show at least.
57. Going Out Of Her Head
I was the one who ruined the date. A dude who I randomly started a convo with at a cafe once asked me to go with him to an indie film screening the next day. Halfway into the movie, I developed a huge migraine and promptly puked into my soda cup. The poor guy had no idea how to react. Meanwhile, the old couple behind us started audibly laughing at us. Not exactly a pleasant experience.
58. Luck Or Skill
I was on a first date, and we were comparing extra-curricular activities. He was in a bowling league and played softball. I was on a dart league and played volleyball. We were talking about darts and whether it was or wasn’t an activity that demanded some sort of skill over luck. I felt a bit insulted by his patronizing attitude, and before our food even came we started to argue across the rather large booth where we sat.
He said, “FINE, since you’re so skilled at darts, see if you can get an ice cube into my mouth from there,” and I said, “FINE, open up!” He opened his mouth, and I totally just launched an ice cube straight into the back of his throat. His eyes bulged and he clamped his mouth shut, grabbed his throat, and fell over in the seat.
This waitress that had been standing nearby, shaking her head at our stupid argument, ran over to help when, he sat up, threw the ice cube onto the table, yelled, “SCREW YOU!” and stomped out. I said that I was really sorry, that I didn’t mean to get it into his throat, blah blah, but he kept on stomping and I never saw him again. Sometimes it’s better to be lucky than good.
59. Putting On A Show
The worst date that I ever went on was the one where my ex-boyfriend took me to see a play about the women’s liberation movement. Afterward, he informs me that the purpose of this outing was to give me confidence…because he was planning on breaking up with me. I literally had no idea how to react. I had never experienced anything as ridiculous as that in my life.
60. Please Don’t Hold My Hand
I saw a couple in their mid-20s come into my work. It’s obviously a first date, but they seem to really like each other and are getting along well. However, I wasn’t serving them, I was serving the table next to them. About halfway through their meal, I notice them holding hands over the table. Cute. Then, the guy lifts her hand to his lips and kisses the back of it.
A bit of an outdated gesture, but still cute, I guess. The woman seems slightly confused but goes along with it. A little while later, I see the guy do it again. Okay, dude. Then again. The woman is confused and looks a little uncomfortable. They are no longer holding hands. I go to serve my table and see the dude full on MAKING OUT with her hand, tongue and all.
The woman looks extremely embarrassed, and uncomfortable, looking everywhere but at her date. I go over, and casually ask if they need anything, and the dude stops. Woman yanks her hand back. She left pretty soon after.
61. Happy Birthday?
The worst date that I have ever been on would have to be the time when my date got completely intoxicated at my good friend’s birthday party and then left with another girl. Yep, you always know you’ve chosen well when they can’t even make it through the first date without letting their attention wander off to other people…
62. Pay Your Way Out
I was new to the DC area, and being so new to the area, met a girl from a craigslist ad. She seemed nice, we had some common interests, and talked for a bit and decided to get coffee, which then led to a movie, and a dinner date. She wanted to invite her best friend and her friend’s boyfriend, and do a double date—that was fine.
But come date time, the guy was “busy” with work, so her friend was the third wheel. We had coffee, I paid for all three of us, then the movie, I paid for all three of us, which was not a problem for me. After the movie, we move towards dinner, and her friend’s boyfriend has finally showed up, so I think, “that’s cool.”
We go to dinner, and all he talks about is his job, all she and her friend talk about is his job. He works IT for the government, I work IT for a private company, we exchange banter about IT, but the girls keep talking about how much money he makes working IT for the government, and I am just done with this line of conversation.
They are all comparing me to him. Whatever, I maintain a nice demeanor, but am not having a good time since every topic revolves around him. When it comes time to part ways, I ask the server for the check. It’s just a little over $100, and I want to leave. She asks how to split it, I said don’t bother, I got it. Then comes climax of the horrible night.
Dude who was talked up throughout the meal wants to pay, I said I got it, he insists since he missed the coffee and a movie, I insist back—mostly because I wanted out, and wouldn’t chat before placing my card down. He further insisted. I just said fine. Later that night, the girl, who was otherwise nice until her friend and friend’s boyfriend showed up sends me an upset message about why did I let him pay, etc. I had a steak, etc. So did he!
63. Store-y Time
Years ago, I went on a first date with a guy during the daytime. We decided to go over to his parent’s house to swim. On the way, we stopped at a 7-11 to buy some sunscreen. After I buy a bottle, we get in the car and this guy pulls a candy bar and a magazine out of his pants. Yep, he had shoplifted from the store while we were on our date!
64. Leaving So Soon?
I once went on a date that seemed pretty decent in and of itself. Then, after I went home, she continuously hung out in my parking lot for over two hours after she dropped me off “in case I changed my mind about doing something after dinner.” Umm, if the answer to that wasn’t a definite no before, it certainly is now…
65. Double Trouble
I sat next to one heck of an awkward first date. It seemed there was an older couple setting up two younger people, and the four of them were on a double date. Anyway, the young guy was a complete jerk. I distinctly remember him telling a drawn out story about his shirt, and how it had square buttons, and they were better for some reason.
And he bought it at this exclusive place for men, where they have hot women come and fit you for clothes. The rest of his stories were similar, and he did most of the talking. The older woman was enthralled by the young guy’s stories. The older guy, and the young woman seemed annoyed out of their minds.
66. Pay To Play
My worst date was the one with the girl who openly told me that the only reason she was dating was to find someone who would pay her rent and pay for her kids as well. She even directly asked if I was up for the challenge. Needless to say, it didn’t work out for her. You gotta give her some credit for her honesty, though!
67. Look Out For Each Other
I was the person on a terrible first date. It was unusual because he picked a very fancy location that was way out of town—like an hour drive. I normally prefer casual dates like walking in the park or coffee, but he insisted we go. I arrived first, and when I sat down I ordered a drink—strawberry lemonade, as I don’t drink —and was talking to the waitress, saying I was waiting on a date.
She was super nice to me and said, “Oh, I hope it’s fun, good luck!” Once he arrived, suddenly her mood shifted, and she gave him an attitude when he ordered. He was trying to coerce me into getting something harder, but I was firm and said I would stick to my strawberry lemonade. Throughout the date, he kept trying to order me stuff.
The waitress was being really weird and kept complimenting me, giving me free lemonades, refills every two minutes, and basically giving him dirty looks. She stayed close by always watching. The guy was being a jerk about the situation, and started acting rude, saying, “I hope she’s not gonna charge for those.” He looked incredibly angry and uncomfortable.
I was starting to wonder why this waitress was being so mean, so I went to the bathroom and waited to flag her down. She told me he goes there every other weekend with a new girl, and that the girls would walk out of there acting very tipsy. She suspected he roofied them, and wanted to make sure I was okay and kept changing my drinks to make sure I wouldn’t get screwed up.
I did confront him, and demand he empty his pockets, he didn’t have anything, but admitted he gets girls to sleep with him via pressure tactics. I took off right when he said that and the waitress took me to my car, I made sure to give all the cash I had as a tip. I seriously love that waitress, and I’ll never forget her.
68. Food, Glorious Food
I once went out on a date with this guy who ordered a ton of food to our table and then refused to eat any of it because he was apparently on a diet. That probably would have been a good thing to mention earlier on. He just sat there and watched me eating on my own the whole night as he told me a whole slew of extremely detailed stories about his gambling problem.
69. Should Have Stayed Home
My date said that she had been sick but was looking forward to getting out of the house. So we went out to a restaurant, and somehow the smell of the salad bar made her go to the bathroom and vomit. Like, drop her water glass on the floor where it shattered, and drop her purse on a table full of people on the way to the bathroom, and then you could hear her vomiting. Yeah, she was sick, I guess. And then she was so embarrassed that she would not talk to me afterward. The worst part? She was HOT, gosh darn it!
70. Pop Goes The Weasel
I once went out on an eHarmony date to a high-end bar with a huge selection. The girl shows up and she doesn’t look anything like her photos. She drank 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.
71. Thems’ Marryin’ Words
I picked up my girlfriend one evening, planning on proposing to her. I took her to one of our favorite parks and surprised her with a picnic, which we both enjoyed. When we were done, I sat on the ground next to her, looked into her beautiful green eyes, and said “I love you so much. Will you marry me?” She replied with a shocked look and said something like, “Oh sure, whatever.”
My proposal had caught her off guard and went completely over her head. So now, in my mind, I am thinking, “Oh, you idiot. You screwed this up bad.” And then, out of my mouth, came the stupid words: “No you idiot, I’m proposing to you!” Chalk that up to an extreme case of nerves. On the bright side, despite her confused expression, she said yes and we’ve been married for 11 years now. Our first child is due in a few days.
72. 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 and we’re smoking right now, 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, I nearly yelled.
Sure enough, it turned out that when they said “smoking,” they didn’t mean the light 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.
73. 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.”
74. 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…
75. Picture Perfect
I chatted, exchanged photos, and agreed to a first date with this girl I had met online. After seeing how different she looked in real life, most of the dinner was then spent in an active discussion over what a “recent photo” meant. We had to agree to disagree with her opinion that “any photo will do,” and my opinion that “any photo more than ten years old will not do.”
76. Whine About It
I worked as a waitress in an Italian restaurant while attending university in 2006. An obvious first date comes in. He’s booked it and requested a table in a secluded area of the restaurant because the acoustics would be perfect. She arrives and asks to move to a table to by the window. No big deal, but he’s annoyed at this.
They ordered a carafe of the house red with their meals. Anything she said, he’d turn it into some achievement he’d already accomplished. He kept making comments about her order, such as how fattening a dish would be, and then proceeded to say his family owned a vineyard, and he knew a good red wine when he smelled one.
He then asked for the most expensive bottle on the menu, and to take away the what he called, “poor house red” then talked about how the bouquet was different, and the clarity was so much better on the “expensive” drink. When it came to dessert, she had enough of his behavior and flipped when he said that she shouldn’t have any, or she’d end up with stretch marks.
She was a bit overweight, but not overly so. She stood up and yelled at him for being a condescending piece of crap, for knowing fudge all about vineyards, and dropped the coup de grâce that her father was our wine supplier and that the house red was exactly the same as the most expensive bottle—all of which was totally true. He was left speechless with the full check to pay.
77. Grunting And Groaning
I once had a blind date with this just painfully shy, rude, and aloof young Russian girl. I mean, I guess we just didn’t click or whatever, but man she made it so darn awkward! She’d literally grunt in disapproval at everything I said, and she kept on complaining that she was so bored. When the waitress came back for the check, I blurted out “SEPARATE!” before she even asked.
78. 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!”
79. Taking A Scab At It
I once went on a blind date with a lady who wouldn’t stop picking at her scabs all night. She literally made a pile out of them on the restaurant table. I excused myself to use the washroom. When I came back, my soup was there but the pile of scabs wasn’t. No, I didn’t eat the soup…
80. 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.
81. Don’t Be Cruel
I worked for IHOP for a very long three months. Most of my experiences were decent. On one occasion, one of my acquaintances came in with a date. We had been friends as kids, and still sometimes chatted amicably. At this time, I had a stutter that would happen if I spoke too quickly, was stressed, or just trying to speak hard words.
I went up to their table, said hi to my friend and her date, and instantly flubbed the greeting with a stutter. Honestly, my stutter has never bothered me, never felt like a bad thing until that moment. Her date looked at me, did that little condescending laugh that we’ve all heard before, and then repeated what I said while mocking my stutter.
I could see my friend physically recoil from him, her face clearing showing a “did you really just act that way?” expression. At the time, I just brushed it off. It bothered me for about two seconds in the moment, but even years later I still haven’t forgotten. Still, I could tell with that one little moment of acting like a jerk, my friend was not going to go on a second date with him.
82. Dirty Dancing
I once accidentally pooped in my pants while on the way to the bathroom during a date. My underwear was ruined, so I threw them out and returned to dinner with nothing between my pants and my skin. I think it’s safe to say that this was my worst date of all time.
83. Mommy Dearest
I work at a bubble tea restaurant right near a college. It’s a nice hangout spot with dim lighting, comfortable furniture, and board games. A lot of first dates happen here. Probably the worst I’ve ever seen was this guy who looked somewhere between 17 and 19 years old. He was meeting up with this girl around the same age.
They got teas, took a seat, played a board game, and talked. His mother sat at the table next to him the entire time, and just stared them down. It made me feel so bad for him—but the icing on the cake is when she goes up to them at 8:30 pm and tells them that it’s time for the two of them—her and her son that is—to head home.
The guy is visibly upset, but says goodbye to his date, and follows his mom out. The girl comes up to order another tea, and I asked her about it. She was more than happy to fill me and the other girls in. This lady had essentially injected herself into the date, interrupting their conversation and critiquing her son’s behavior.
84. Lip Service
I once met a girl on Tinder, and we texted for about a good month. Then, one day, my parents were away on vacation so I finally convinced her to come over to my house to spend some time together. As soon as we started kissing, I somehow bit my lip and started bleeding uncontrollably. I had to go to the ER. She does not want to see me again.
85. A Lively Woman
A friend and I meet up and a chain restaurant for a meal and a catch-up, in the booth across from us are a guy and a girl in their twenties, very obviously on a date. Things seem to be going moderately well, just kind of let them do their thing in the background as my friend and I chat about life and stuff. Then, the guy stands up halfway through the girl’s sentence, cutting her off.
It’s quite a violent movement, so it draws the attention of most tables nearby. The guy then says, in a way that makes me think he has rehearsed: “I’m sorry Jen. I just wanted to give women one more chance, but I can’t do it, you’re lively, but women just aren’t doing it for me.” The guy throws some money on the table and walks out. She kind of sits there with everyone looking at her, going redder and redder.
The lovely waitress swoops in, and saves the day for her, but wow. Never seen anything that completely insane before or since—at least just wait for the date to be over and politely decline a second.
86. A Tall Tale
My roommate once set me up with a guy who made it known that he was very irritated by the fact that I wore high heels on our date. Why? Because it made him feel smaller. Note: he was still taller than me by several inches, just less taller than he would have been otherwise. All in all, he was definitely not the man for me.
87. Show Off Your Interests
A couple of years ago, I was tending bar at a high-end steak joint. A pretty brunette walked in and sat down at the bar. After fixing her a cocktail, I asked if she’d like to see a dinner menu. She explained that she was waiting for a date. A few moments later, the guy arrived carrying a large bag. It was immediately obvious this date was their first. It went badly so fast.
Their conversation was lurching from forced, to downright painful when he reached into the bag and pulled out an album containing…his Pokémon card collection. He set the book on the bar and thumbed through each page, thoroughly, and lovingly describing every card, attempting to educate his date in the ways of Japanese pocket monsters.
I’ll be fair to the guy—dude was passionate. She feigned an emergency, and called her friend to pick her up. He stayed and ate a plain hamburger at the bar.
88. Nice Car, Awful Guy
My mum went on a date with a guy who picked her up in a fancy car when she was young. She pointed out a cute rabbit eating grass near the side of the road, so he sped up and hit it on purpose trying to impress her. Instead, she cried and made him take her home instantly. She met my dad not long after.
89. 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.
90. Accidents Happen
Bartender here! So, I used to work at a place that was well known for our wings. I witnessed what was obviously a Tinder date go belly up. I greeted everyone and got the ball rolling. After a few drinks, I could tell they were very obviously into each other. I was happy that they were happy. But, as we all know, stuff happens. And it was about to happen tonight.
I make a pass back their way, and ask if they want to do another round. They both eagerly agree, and while I’m making their drinks I hear the guy say, “What do I have to do for a kiss?” Aww, cute. The girl thinks for a second, and then says, “eat a spoonful of their spiciest sauce.” When I come back with their drinks, he asks me for a side of our hottest sauce.
I tried so hard to talk him out of it. When that didn’t work, I did the only other thing I could do and grabbed my cook to witness this idiotic move. The cook brings out the sauce and gives it to the guy. We warn him one more time that this is an AWFUL idea. Guy shrugs us off, and tips back the little ramekin. Things were fine, at first.
Then tears were streaming down his face, I got him some milk, and I thought we were over the worst of it after five minutes pass. I was wrong. Dude kicks off his shoes, stands up, and runs to the back of the bar. As he is running, poo starts escaping his pant leg and leaves a trail all the way to the bathroom. I couldn’t believe it.
He refused to come out until his date left. He never got the kiss! I just cannot believe this guy had the forethought to take off his shoes before he publicly pooped his pants. To be fair, they were really nice kicks.
91. Hitting Rock Bottom
About 10 minutes after picking a girl up for a date, she asked me to pull over to the side of the road for a minute. She then got out of the car and proceeded to take a poop on the sidewalk right in front of me.
92. Gone In 60 Seconds
A girl and guy came into the barbecue restaurant I worked at. They met at the door exchanging the usual, “Hi, nice to meet you!” pleasantries. The guy was a complete jerk. She ordered ribs, and he said, “Do you want to keep that hot figure of yours or look like that chick over there?” while pointing at a slightly overweight woman nearby.
Then, when they were waiting to pay, he starts flirting with the chick behind them. She waited until he paid then left without waiting for the food. At my work you ordered, then paid, then the food was brought to you. So she left before the date even really started.
93. Bad Luck At The Bus
I am open to anyone, regardless of gender, but this was with a dude. I met a gent while waiting for a bus, we chatted for a while, and he tried to impress me with his playing of the stock market, but I gave him the benefit of the doubt. I actually thought, “why not,” and we exchanged numbers. We arranged to meet that night and go to dinner.
There was an arcade I frequented, so we’d go there after. He picked a buffet near where I worked at, it was like 4.99 to eat there—and you DEFINITELY got what you paid for. I was really into goth culture at the time; when he met me on the bus, I was dressed for work, so he seemed confused about my attire. He brought out a Bible, and read some of it to me, too.
So, I find out he had no transportation plans so whatever, I shared a car with siblings, and was able to use it, so I drove us to the arcade. He increasingly got frustrated he couldn’t “kick my butt,” even though every game we played, he never played and, like I said, I frequented the arcade so I was well-versed with them. He also didn’t realize I knew how to play pool.
I’m really bad at it, but was better than him. Played some old fashioned arcade games, and won some tickets. I hate ticket prizes, so told him to give the tickets to a kid. Instead, he got me some crummy bear. He also told me he didn’t wash clothes, but just bought new shirts when things were dirty. I told him I was ready to go home at around 11 PM—I never gave up an opportunity to hang out at the arcade, after all—and I would drive him home.
Turns out, his family disowned him, and he had been living in an Econo Lodge hotel for the last six months. I tried to avoid his calls, and then he started calling from a different phone number. I told him I didn’t want to go out again, and then three years later I thought it’d be funny to login into Myspace, and he had messaged me recently there saying we should try again.
94. Right Place, Wrong Time
I worked briefly as a waiter at a semi-nice place near where I live. I once had a couple come in for a date who we had seen there a few times before. I think we were their regular dating spot. But today was different. The girl was clearly very sad, and was talking about how her uncle was really sick and was probably going to pass soon. That’s when the guy made a ridiculous error.
In the middle of this discussion, the guy decided to pull out a ring and pop the question as if nothing was wrong. Seriously, dude? Read the room!
95. Not-So-Secret Admirer
I was a bartender at a country club. I once watched a woman curse her husband out at their table because her kept flirting with the waitress. She got really loud and made a huge scene. Eventually, she stormed out of the restaurant, with all the rich snobs watching. The waitress felt very guilty about it, but she told me that the guy had been coming in there often and tipping her 100% of the bill every time.
96. Bad Date Topics
We had our flight canceled due to a snowstorm on Christmas Eve. The only place open for dinner was an Indian restaurant. There were a few customers in there. It was an interesting looking bunch, sort of what you’d expect eating out on Christmas Eve. This one couple though looked to be in their 40s. A guy and a woman.
She never said a word and looked like she was in a trance. The guy though kept talking at her in this slow monotone: “And another thing I hate about you,” and proceeded to critique her while she continued to stare into space.
97. Au Revoir, Shirt!
I used to work at an upscale fine dining restaurant in Vail, Colorado. I once saw a lady walk in off the street, throw a glass of red punch all over a guy’s white shirt, and then leave. The guy did not react at all. He just sat there and continued eating his spaghetti plate as if nothing had even happened. He could not have cared less. It was hilarious.
98. Fire And Ice
First date. We went ice skating. She fell. I accidentally skated over the back of her hand. The blood on the ice was a sight to behold. She wouldn’t speak to me as they put her onto the stretcher and took her away. The last I ever saw of her was as the ambulance doors closed. Needless to say, I did not get a second date.
99. Double Whammy
I once took a girl out for sushi as a first date. About ten minutes into it, I got a call from my boss. Ordinarily, I wouldn’t have taken the call, but this is not the kind of guy that you can ignore without some major consequences. I went outside to take the call where the guy berated me throughout the entire conversation. Great—but then it got cruel.
He ended it by saying he’s sorry he interrupted my dinner but he’s not sure I understood what it takes to be his assistant. I walk back in, my confidence utterly destroyed, and proceed to be completely in my own head for the rest of the date. As I dropped her off outside her house, she says, “You might be the most awkward person ever.” The next day, I was fired.
100. Empty Your Pockets
The most awkward date I had? When his wedding ring fell out of his pocket midway through dinner. It was our first date.
101. 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.