When it comes to dating, hope springs eternal. Even though we go through dud dinner after boring movie night, we still hope that the person of our dreams is just around the corner. Well, abandon hope all ye who enter here: These are some of the most disastrous dates to ever happen, and believe us when we say that these people are better off alone.
1. Make Up Your Mind
We met at his house before he took me out to a “surprise” lunch that he planned. It turned out he just drove us to a McDonald’s. But it got so much worse from there. He turned to me and said, “By the way, I invited my ex to join us for lunch.” I would have left before she got there, but since he took me in his car and taking a taxi back to his house to get my car would have been expensive, I stayed.
The ex was actually really nice and tried to make things less awkward. She didn’t know it was a date; she thought she was just meeting with her ex for lunch. She was just as shocked as I was. While my date was in the bathroom, the ex confided in me that she was hoping they would get back together. I told her that it was fine because I had no interest whatsoever at that point.
After lunch, he took me back to his house and the ex came too. He tried to put a movie on but I insisted on leaving. His response was mind-boggling. Despite the fact that he clearly didn’t want me, he took my car keys off the bench and locked himself in his bedroom while he hid them from me. His housemate had to help me find my keys.
He later started the movie with his ex and I left without saying anything more. There was no second date and those two ended up back together a few weeks later.
2. Just Desserts
I brought a girl back to my house for dinner and a movie for a date. I had previously made a “bet” with her wherein if she won, I’d make her dinner and bake a pie, but if I won, she had to make out with me. Either way, win-win, right? So we finished dinner and went back into my bedroom to watch the movie we had planned to watch.
Midway through the flick, she said, “I’m still a bit hungry—I think I’ll go grab a quick bite of the leftovers.” She got up and went into the kitchen. I decided about 45 seconds later, as my stomach rumbled, that that sounded like a great idea. When I arrived in the kitchen, my jaw dropped. There she was, standing over my silverware drawer, emptying everything into her purse.
I was shocked. I asked her, “What the heck are you DOING?” She giggled and replied, “Oopsie!” I’d have been angry already, but the girly giggling just put me over the edge. I walked up, looked in her bag, and saw that she’d only managed to grab some of the inexpensive silverware so far. At that point, I reached over to the counter and grabbed a slice of the pie.
I looked her in the eyes and said, “Don’t forget your dessert.” While holding her gaze, I dropped the pie into her purse and smashed it up as best I could with the sides of the purse to make sure it got in there nice and good. I kicked her out and never saw her again.
3. Oceans Away
I convinced a girl who I was crazy about to go out on a date with me. I knew I had to make it count. We lived by the ocean and she had dropped the hint that she had never been out on the pier at our local beach. Challenge accepted. I nervously drove her down to the beach and we proceeded to slowly walk out on the pier together. I should have known it would all go wrong.
She seemed hesitant from the beginning. We stopped near the end of the pier and I leaned against the railing over the water while she stood back a bit from the edge. She didn’t really seem into it at all. Awkwardly, I said, “This is a great view, huh?” just as two pigeons flew up and landed at our feet. “Sweet, chicks dig birds,” I thought to myself.
To my horror, the birds began to make passionate pigeon love in front of us while neither of us spoke. I had never witnessed such violent passion. I quickly scanned around and saw a couple holding roses on the other side of the pier. “Awesome, they look romantic; chicks dig romance,” I thought to myself. We quickly walked away from the surprisingly forceful pigeon action and stood next to the happy couple.
The man and woman were holding each other, but something seemed off. I glanced up and noticed that they were sobbing. The girl I was with noticed too. As we were both looking, the couple took their roses and cast them into the sea. I had posted us up next to a darn funeral; some kind of sea burial.
Between animal lovemaking and this, I had executed one of the worst dates of all time. Just as I had accepted my failure, my date started getting fidgety. Based on her body language and her expression, it dawned on me that she hadn’t told me about the pier as a “hint,” but because she was terrified of it. Turns out, she had a fear of heights and the ocean.
That pier will forever be a monument to my most unsuccessful date.
4. Malice In Chains
I was dating this girl who I later realized was pretty much using me to buy her stuff. But it’s the way I found out that hurts the most. I took her out to dinner and surprised her with concert tickets to Jerry Cantrell of Alice in Chains. She was excited; so much so that she proceeded to spend the rest of dinner on the phone telling her friends about it. Kind of rude, but no big deal.
Fast forward to the night of the show. I took her to dinner and she acted ice cold. She barely made conversation and shrugged me off every time I tried to. Huh. We took the sky train down to the venue, and when I tried to hold her hand, she immediately pulled away. Huh. We get to the venue, went inside, and I bought us a couple of drinks.
She curtly thanked me for the drink and then said she’d be right back. I grabbed my drink and headed to the stage. When I got there, I saw her and my stomach drop. I saw her talking to some other guy. It quickly became clear that they were together, or at least had been before. So I walked up and said, “There you are. What’s up?”
She replied, “Oh, it’s you. Hi.” She turned to the guy she was with and introduced me, saying, “This is my friend.” The guy then gave me a nod and a look that pretty much said it all. They were together, and I’d been played like a fiddle. I was in a horrible situation. Jerry Cantrell was to go on stage in the next 30 minutes, and I was going to have to make a tough decision.
I could either go home, wallowing in misery, or stay and see the show, knowing the girl would be enjoying it with her guy no less than 20 feet from me. Ugh. So, I did what any other Alice in Chains fan would do. I drank a ton and sloppily danced for the next two hours, trying to ignore that stinging feeling. The show was great, and the crowd was awesome (minus those two), so that was a plus.
I went home as soon as Jerry left the stage. I said “screw you” to the girl on the way out, and pretty much sobbed on the ride home. The worst date I’ve ever been on.
5. Mixed Messages
I went out on a date with this girl in her first year of college. For some reason I’ll never fully understand (maybe she was trying to sabotage the date), she chose for us to see the movie Borat. For those of you who just don’t know any better, there are certain people you go to see Borat with, and there are people you don’t.
I will never get over the awkwardness of trying to be romantic while Borat gets tea-bagged by a ginormous foreign man. Yet, it still got worse than that. Just beforehand, we were sitting at the cafe next door, chatting. It was going pretty well regardless of her movie choice, which had the potential to totally ruin the night.
Suddenly, I saw this guy I knew from high school. He walked up to say hello and ask what movie we were seeing. I told him “Borat” with a straight face, and he said, “Ohhhhhhhh, no! That’s a terrible first date movie.” God, I still think about how this girl replied to him. Before he could say anything else, this girl said, “Oh we aren’t on a date.”
No, I just picked you up, bought your food, and bought you a movie ticket.
6. Let’s Not Meet Again
I do believe I have the worst date ever. I mean… ever. So, I was newly single from a bad breakup of five years. She left me for another gal, and her friends decided to “right a wrong” and rob me of everything I own, save for my dog, bed, and SOME of my clothes. Anyway, after a few months, I tried a dating website. A gal messaged me.
I was like, alright, your picture looks okay; you type a little immature, but your text is sterile. Still, I decided to give her a shot. We met in a public mall that had shops and restaurants. I thought to myself, if things don’t work out well, that’s fine; we can go our separate ways. So I went there, and she messaged me where she was in the mall.
I made my way over to her location and when I saw her, I stopped in my tracks. There was a girl, but she looked nothing like her profile. She photoshopped her pictures. Still, I didn’t want to hurt her feelings. I figured I’d chat with her and see what was up. I introduced myself to her and she said hi, then we walked through the mall.
I noticed after a few minutes that someone was following us, shop to shop. “Oh, that’s my mom,” she said. It bothered me a bit, so I asked why is her mom was following us. By the way, we were both 25 at the time. She explained that her mom came along for the meet… with her brother-in-law and his wife. The gal kept trying to kiss me in every store, but her mom was literally in the other aisle giving me the evil eye.
It was freaky as heck, and not in a good way. So after an hour, we went to the food court and got some food with the entire family. Didn’t these people have somewhere to be? They seemed nice, but it was just too darn creepy. They later invited me back to their place for cards and “family games.” But it turned out, the real reason wanted me back at their place was so they could grill me about their daughter.
Not good for me. My stomach started acting up as we were finishing up dinner. I excused myself to the men’s bathroom, where the feeling of needing to “go” intensified, quickly. I entered the bathroom, downing an Imodium as I entered. I was sweating and I did not feel good at all. As I saddled up to the toilet, the pain moved into my kidneys.
It wasn’t food poisoning—my stomach was fine, but I felt like I had an iron spike moving in my kidneys. It was bad. I saw her outside the bathroom and she said her family had gone to meet us nearby. She wanted me to follow them to their house. Since we were parked at different areas of the mall, she told me to meet up with them at a nearby Denny’s.
While driving there, my body felt like it was on fire. The pain was so intense that I was afraid I’d broken something. We got to Denny’s and I raced inside. “Customers only,” the sign said, but I didn’t give a hoot. I got into the bathroom and pulled up to a urinal. At this point, I was either going to poop my pants, pee an iron spike out, or pass out.
I actually briefly passed out for a second. I caught myself falling against the wall in pain, but nothing was coming out. I zipped back up and stumbled outside. My date was standing next to my car, and the world turned gray… Such a weird feeling.I fell onto the grass on my knees. The pain was so intense, and I was a half-second from passing out.
I tried to mumble something to her about being in mortal pain while she was crouching over me, a half-inch away from my face. I wanted to puke on her, but I was in so much pain. She closed her eyes and moved in closer for a kiss. A KISS! While I was passing out in pain. I pushed her away and stumbled to my car. I’m not sure how I made it to the highway.
I should have gone to the hospital. Once I got back to my apartment, I went to the bathroom and the pain was gone. There was a little kidney stone in the toilet.
7. Come Again?
On evening, I was in the middle of getting it on with some guy I’d just started dating. He must have misheard something I mumbled as “I love you” because he said, “I love you too.” At that moment, I entered an entirely new level of despair trying to decide how exactly I was supposed to respond to THAT. I did not respond well.
Tragically, I panicked and rolled with it. Chalk it up to social anxiety. The hope was that I would fall in love with him eventually. I didn’t. By the way, there were so many mortifyingly cringe-worthy moments with this guy in the next couple of months that we dated. Here are some that I remember: He thought the concept of “the carpet matching the drapes” meant that he was supposed to trim his nether-regions to match his haircut.
Once, he accidentally called the placebo week of the birth control pill “the placenta week.” I never forgave him for that. There’s a phrase I say to myself a lot to keep things from getting to me: “But you already knew that, didn’t you?” It’s silly, but it helps me for some reason. I wrote it on my arm once when I was having a bad day.
When he saw it, rather than having the normal human reaction of asking what it means, he said, “You don’t really believe that, do you?” I’m still not sure exactly what was going through his head. That’s the first and last time I date someone whose looks are better than their personality. The guy was freaking gorgeous, but he acted like three raccoons in a trench coat desperately trying to pretend they are a human.
8. A Wild Ride
This was several years ago before everyone had cell phones. A cell phone would’ve made things tremendously easier, now that I think about it. So this girl saw me on a personal ad and. hit me up. We seemed to hit it off. She was a little older than I was and her picture made her look a little bigger than I’d normally go for, but whatever.
It was kind of weird that she wanted to pick me up rather than meeting somewhere, but I was still game. I should’ve stopped everything when I saw that dingy old Honda Civic roll up. The girl ended up being a LOT older and a LOT heavier than I expected. I didn’t say anything though at that point because I didn’t want to offend her.
So I got into her car, which was full of trash, and we set out. She told me she needed to swing by her place and I said sure, whatever. Her place was in the rough part of town, which creeped me out. She invited me inside and I figured it was better than sitting in the car waiting. So I joined her inside, which is when things really took a turn for the worse.
It turned out, her boyfriend and kid were living in her apartment, neither of whom she mentioned to me before. Her boyfriend was remarkably laid back about me wandering in; meanwhile, her kid was toddling around, oblivious. Sometime later, we headed to the car. She started driving and we began discussing where to go for dinner.
I recommended a really nice restaurant, but she said it was too fancy. I also suggested a quirky hole-in-the-wall that’s kind of gross but has fantastic food, but she didn’t want to go that way. She suggested Taco Bell. I make a noise that was somewhere between “uhh, okay” and “really,” which she took as me agreeing, and so we went to Taco Bell.
At this point, I was just happy to not be in her neighborhood. I ordered a couple of tacos, and, being the gentleman, I paid when she ordered what seemed to be half the menu. Then, she said she needed to use the bathroom. That was my chance. Without even thinking about it, I was out the door and halfway down the block before I even realized what I was doing.
A little later on, from a distance, I saw her burst out of the Taco Bell, look around, then start shouting for me to come back. Then I saw her get in her car. I thought she was just going to go home, but no… she started looking for me. This particular Taco Bell was on the main drag that backed up to kind of a residential neighborhood, so I wound up hiding behind some hedges and shrubs as she patrolled the streets.
This went on for two or three hours, with me skulking in the bushes as she circled the block. I’ve dodged officers that were less determined.
I managed to work my way back to my building, only to find her waiting in her car out front. Luckily, she didn’t know about the back entrance, so I snuck in that way and left all my lights off.
I locked and barricaded the door because she refused to leave. The sight of her lurking in the parking lot at that late hour prompted one of the neighbors to call the authorities. She still refused to leave. She called the officers a number of interesting profanities and, judging by the screaming I heard from the parking lot, they decided to take her in for disturbing the peace.
9. Something’s Fishy
My date and I were having a nice dinner of salmon and roast potatoes at a dining hall. As he started talking about his day, I took a bite of salmon and felt a horrible pain slide down my throat. Not knowing what the heck that was, I tried drinking some water. Deep in my throat, I felt like I was being attacked, and every gulp only made it worse.
Then, I made a chilling realization. This must be that stupid thing my mother had always warned me about when eating fish—that you have to be careful of fish bones or they will get stuck in your throat. Well, darn. I spotted some potatoes on my plate and started shoveling them in my mouth; you know, to try and knock the bone out or push it down. Then the guy started telling a joke.
Well, my plan backfired, and once again, the pain became much, much worse. By now, it felt like someone had driven a screwdriver into my throat and was occasionally shoving it in deeper. When the guy finished his joke, he paused as he looked at me, awaiting laughter. I burst into tears. He said, “That bad, huh? I’m sorry… I-I’ve got other jokes…”
I managed to whisper that I had a fishbone stuck in my throat. He blinked. “But it’s boneless salmon.” I didn’t really know how to respond to that, so I just stared at him with tears running down my face. He then said, “So uh…do you want to leave? What do you want to do?” and I whispered that maybe if we just got more potatoes, it would go away.
Three plates of potatoes later, I still had a fishbone in my throat, plus I was overly bloated. I never want to see a potato again in my life. This guy just watched in confusion while I ate potatoes and cried. When I looked up, he asked if it was still there. I nodded. At some point, we decided to go back to my room. Then, as we passed by the salmon station in the dining hall, he made it so much worse.
He pointed at the sign: “See? It’s boneless.” I didn’t respond. When we got to my room, I called my mom and she said I needed to go to the hospital to have it removed. Freaking out, I turned to go and he insisted on coming with me to make sure I’d be okay. Sweet, right? Well, once we got there, he wouldn’t leave. We waited six hours before any doctor or nurse would even see me in the ER.
When a doctor came, it was some practicing med student who, without looking, said that most people think the bone is still there when it’s not. Apparently, salmon bones don’t show up on X-rays, so he told me to go home. I refused, having just had the bone partially dislodge then re-lodge, punching a second hole in my throat. He said too bad, then went to get me check-out forms.
Then, the resident doc came and reamed the student out. I was thinking, “Oh thank god, they’re actually going to fix me now.” He told the student, “No, we won’t release her until we’re sure it’s really gone; she could choke or it could puncture her lungs.” Okay, really scary, but okay, they were going to fix it. So the doctor took me into a room and the student came trooping in after him.
He brought in this weird box thing with a long cord and a slightly larger thing on one end. He told me that, luckily for me, there was this new technology that can pick up salmon bones, and all they have to do is stick the cord through my nose and down my throat. I was not a fan of this idea. Even worse, he said he didn’t have time to do that, and that it would be “good practice” for the med student to try it for his first time.
All the med students and nurses in the freaking ward came in to see this new technology, which made the med kid nervous. His hands were shaking. They sprayed some numbing stuff into my nose (most of it missed) and then the kid with shaking hands tried to stick an electrical cord down my nose while 15 people watched.
That’s when the pain came. The med student said, “There’s resistance,” but the nurse urged him to just keep pushing. At this point, I had two holes in my throat and an electrical cord up my nose that was too big to fit, but the guy was still jamming it in. I started crying again. Not sobbing or anything, just tears rolling down my cheeks out of sheer pain.
This apparently freaked the kid out more, and my shaking got worse. I didn’t need to see it; I could feel it in my nose. Once the camera finally went in, the kid looked through and said he could see the bone. “Uh-oh—it’s right there, in her vocal cords. That could mean serious damage,” he noted. So he took it out and the docs arranged for an ear, nose, and throat doctor to come in the next morning and remove it.
They said they couldn’t do it themselves because they could permanently damage my vocal cords. Awesome. Here’s the kicker. The 15 folks watching the cord procedure all wanted a turn. The resident doc came in and told me how important it was that people got the experience. So I felt bad and gave them permission—all 15 of them—to practice with the cord thing on me.
This was an hour and a half ordeal of them sticking the cord in my nose and pulling it out again while lecturing each other on technique and such. The entire time, the poor guy I was on a date with was sitting in the waiting room. He must have been. there for about eight hours, on a school night no less. A nurse came in, gave me a pill, and said it would “relax” me before the operation.
This was about the time when the nurses realized I had someone waiting for me in the waiting room. They told him he could come back and visit me. The next morning, they put me under, got the bone out, and sent me on my way. During my classes in the afternoon, I had a spontaneous nose bleed that was pretty bad. I tried to cover it up with tissues until the person next to me turned, saw a ton of bloody tissues, and freaked out. I left.
The guy texted me several days later and kindly asked if I wanted to try re-doing our first date. I told him I’d be happy to.
10. Can’t Buy Me Love
When I got to the restaurant for my blind date, she was already eating appetizers. Then, she ordered the MOST EXPENSIVE dinner on the menu and told me straight-up that she did it because she knew I would be paying. Small talk failed, and for 45 minutes, she complained about how no one was refilling her glass every time she downed her (many) drinks.
She mentioned how she heard I make a decent salary. I tried to be civil and change the subject. Awkward conversational topics ensued, and nothing even close to date etiquette followed. A third of the way through, I went to the bathroom. Then, our waiter walked by and asked me an outrageous question. He was wondering if we were on a reality show or something along those lines because he had seen this disaster in motion on TV before.
We talked about how wild the woman was for about five minutes before asking him to stop at our table and ask about the bill. I immediately said split checks and gave him 80 dollars. The date looked shocked and ended up not being able to pay her bill, so the friend who hooked us up got a call and flipped the rest of her check. Her total came to be about 75 dollars. Last blind date for me, ever.
11. Nightmare In Paris
I went on a rollercoaster of a date with a French guy in Paris. It was summer and we were meeting on the steps of Sacré Cœur. We arrived and he brought a bottle of red. I then jokingly said, “Oh you got red…in the summer!” He responded with, “Oh, I guess I’m trash for getting the wrong kind.” After he said that, I immediately knew I had made a dire mistake.
I reassured him and told him I was just teasing. During our conversation, he kept complimenting me incessantly. Like to the point where I got uncomfortable. After like 10 compliments, I didn’t even know what to say anymore. At one point, I was telling him a story and he kept interrupting me to say, “Your eyes are so beautiful; I can’t stop staring at them.”
I was like, “Thank you, that is so nice…Okay, back to my story.” It was nonstop. After the 19th compliment, I heard him mumble in French “…And I’m waiting for you to say the same to me…” I spoke up and asked, “What was what?” And he replied, “Oh nothing.” Apparently, he didn’t think I spoke French, but I am actually fluent.
So THAT was uncomfortable…shoving compliments at me and pouting when I didn’t give him one back. Like sir, if I wanted to compliment you I would—I love complimenting people, but I wasn’t overly attracted to him. Red flag number two. He asked me if I’d been on many Bumble dates to which I said yes, many.
I’d been single for a while and so I went on dates often. He didn’t like this. He began asking me why I hadn’t settled down with any of my past flings, and I explained that I’d met lots of really great guys but it just never clicked. He then got weirdly quiet for a few minutes before saying, “You know, not everyone is going to be as perfect as you…Life isn’t a fairy tale…You have to give people chances, you know.”
At that point, I realized I was seated next to a French incel or one in the making. I replied that I never thought I was perfect or better than anyone, and stressed the point once again that I hadn’t settled down because there hadn’t been a strong connection yet—NOT because I was not giving these guys chances.
I explained that dating is a two-person thing and sometimes the guy didn’t want to meet again also. That was red flag number three. At one point on the steps, he started asking me where I lived and I said, “Oh, just down there like two streets down.” He then kept asking me to be more specific, insisting that I tell him which street… Jesus Christ.
Oh, and there were a lot more self-deprecating sentences sprinkled throughout his conversation. At that point, I was just trying to get out of there as soon as possible. As we walked up the steps to the top, I started planning my exit. As I was about to leave, he looked at me and said: “You HAVE to give me another chance.”
I replied, “Listen, thank you for the bottle of red, but I am not going to see you again, I’m sorry.” He then got very upset. His eyes got huge and he started yelling. “I’m educated, I have a CDI… you must give me a second chance.” In France, a CDI is a permanent contract and it’s a big deal because you can’t be fired. Then again, every person I know has a CDI.
And since when does having a permanent contract equate to women owing you something? By now, people were starting to look at us. I kept calmly telling him that no, and at some point, he lost it. He GRABBED my arm while continuing to rant about his CDI. When he noticed that people were looking, he let go.
There was one moment where he got so mad I really thought he was going to hit me. I could see him thinking about how to keep me there without causing a scene, and I just took my chances and ran down the stairs as fast as I could. I was obviously terrified because he now knew the general area where I lived…Thankfully, he didn’t follow me. I never blocked someone so fast in my life.
12. Love Slap
I took a girl who I really liked on a first date to the movies. The movies were probably a bad choice because I couldn’t take my eyes off her. During the movie, I noticed she had a piece of hair hanging down in front of her face. Me, being the gentlemen that I am, saw this as an opportunity to be cute and go in for the kiss. Screw me, was I ever wrong.
thought to myself, “I’ll reach over and move her hair out of her face which will then lead into the kiss and it’ll be cute.” So, I lean in and reach over to move the hair from her face and make my ‘smooth move’….and as my hand got to within 6 inches of the target zone she comes out of absolutely nowhere, reaches up, and moves the freaking hair herself!!
So at this point, I’m 90% committed, hand located somewhere in front of her face, with no clear objective, and not to mention, obviously blocking her view of the movie. I immediately become nervous and I’m having second thoughts about my decision, but I’m a committed and confident guy who doesn’t back down from a challenge. But at that moment, all logic froze, and my cute plan dissolved.
There was no purpose for my hand anymore, yet it was still on a collision course with her face and for some reason, I couldn’t stop it. I reached over and wiped her forehead, taking whatever makeup that was there with me. Leaving her with an obvious stripe on her forehead that was most noticeable during the brighter scenes, lighting up the movie theatre.
She looked at me horrified. She didn’t even have it in her to ask me what the heck I was thinking because she was so shocked. My entire world turned to flames and the room got considerably hotter. And I didn’t get my cute first kiss. In fact, I got a deleted number…
13. Missed Connection
Met a girl online. Yes. I know, but I had had relatively good experiences with this before. I was very much not in the mood for a serious thing at the time either, so I don’t know why I agreed to meet. To be fair, it was super chill. I met her and her friend at some house that they were parked outside of. I walked up to the car, and the girl looked slightly less attractive than the two pictures she had up.
Still, she didn’t seem terrible. At some point, we ended up going to a grocery store because her friend needed something. As soon as I got out of the car, her friend hit me up for gas money. I was confused, but I shrugged it off anyway. Maybe her friend was just nuts, I thought to myself. The girl I was supposed to be on a date with then got out of the car.
She was wearing pants that my grandpa would have worn when he was alive and a Mighty Morphin’ Power Rangers jacket. At this point, I was starting to prepare for an emergency evacuation because this was going downhill fast. As we walked into the store, I started getting terrible whiffs of BO. I realized in horror that they were coming from her.
Keep in mind, we were outside where the wind is blowing, and all of her clothes were on, yet I could still smell her funk. At that point, I knew I need to bail. I feigned interest in whatever she was talking about while I figured out an escape route. I went to the bathroom in the grocery store and called my friend. I told him to call me in no less than ten minutes and tell me I am supposed to be at a party he’s hosting within the hour.
The girl got in my car and finally, my phone rang. We played out the whole thing, yadda yadda yadda. That’s when she asked if I could give her a ride to where she was staying. I told her GLADLY. The whole drive there, she told me this story about how she once stabbed a girl in high school because she dumped a good friend of hers or something.
I was beginning to wonder if this girl was intentionally trying to make me as uncomfortable as humanly possible. NEVER AGAIN.
14. Left Behind My Own Mountains…
Went on a 4-day date/hike through the wilds of Alaska. It was a trip over Raven Glacier, and the surrounding areas. Before we started the hike, we felt a nice breakfast would be a smart thing to do, so we stop at a local diner to partake of the local cuisine. What’s this on the menu? Reindeer sausage? Sounds wonderful!
I’ve never had reindeer before and the little pepper next to the name showed it was spicy, and man I love me some heat! If your food does not bite you back, it ain’t worth eatin’, I always say. So, I eat not one but TWO giant spicy reindeer sausages right before going on a multi-day hike over mountains and glaciers. What the holy heck was I thinking!
After about four hours of climbing up switchbacks. the low rumbling down deep in my guts began. It got BAD. I mean, stomach cramps, bending over in pain, having to stop to take a “dump” every 10 minutes for almost three days straight! I can’t even begin to describe the smell, almost a mix between molten tar and rancid Thai food.
I brought four rolls of bathroom paper. I ran out by lunch on day two. So, boys and girls, never, I mean NEVER try to eat something new, much less spicy before a multi-day trip. The girl? She stayed with me after all that. No idea why, but she did.
15. Turning To The Feet
Was set up on a blind date by a coworker. Things went reasonably well—ok conversation, he seemed to be genuinely nice. My co-worker and her boyfriend double dated with us for moral support. We went back to the co-worker’s house after dinner to watch a movie together. That’s when things got weird. Co-worker and boyfriend left the room to give us some “alone time.”
Immediately, my date tried to kiss me. It was one of those approaches with his tongue hanging out. I nicely rejected the kiss, saying it was too soon for that type of affection for me. So he shifted his attention to my feet. I was wearing open-toed shoes and he grabbed a foot in his hand and asked if he could rub my feet.
I declined and he began to beg. Told me that he loved feet and would love to suck on my toes. I declined again, started to get a bit scared. He made a last ditch effort by asking if he could just sniff them once. I gathered my things and left ASAP. He followed me to my car and tried to beg me in a baby-talk voice to come back, me and my “widdle piggies” (toes).
I kept expecting a camera crew to pop out from behind a tree proclaiming that I had indeed been “punk’d.” I was as nice as possible about everything, citing that I just needed some time to get comfortable with someone before becoming affectionate. I pulled out of the driveway in such a hurry that I squealed my tires a bit.
I had no intention of seeing him again since he had violated my personal space so much. I (probably wrongly) passive-aggressively ignored his phone calls and myspace messages. He couldn’t take a hint though, and called 20 times in one day. I finally manned up and told him that I wasn’t interested in pursuing a relationship.
16. Dinner With A No Hit Wonder
I work at a dinner theater. We usually do proposals where we set up a “random draw” where the “winner” comes up on the stage to win their prize and are then surprised by their partner, who proposes. It’s usually sweet and makes everybody in the room all fuzzy and warm. Emphasis on “usually.” On this night, everything that could go wrong, did go wrong.
This one guy wanted to take it further, and requested to perform a song—he brought his own music and everything. We’re pretty easy-going at this job, so we agree to let him do it. We do the fake draw, the woman comes up on stage in front of a room of 400 people, and the music starts to play. Apparently, this guy was a little nervous, and he compensated by having a few drinks.
So what follows is a messy performance of a song written by this guy that seemed to focus on how he was sorry for cheating on this woman with her sister, and at the end of it, he gets down on one knee and proposes. Usually this gets a round of applause, encouraging the person to say yes, but not after that train wreck of a performance.
The poor woman was just holding her face the entire time and starts shaking her head and says, “No, what’s wrong with you?” She storms off and leaves him and our stage manager on stage to a bunch of murmuring from the audience. The only thing our stage manager can think of to say on mic is, “Well, that’s that.”
The guy ended up staying for the rest of the show and had many more drinks. That was years ago, and it still remains one of the cringiest things I’ve ever seen.
17. A Fork Of A Time
I had a friend who took this girl out to dinner for a first date. It was a disaster right from the start as this girl spent the entire date on her cell phone. Being the nice guy he is, he just decides whatever we’ll get this date done with and never call her again. At one point he gets up to goto the bathroom and on his way back, notices her sweater had fallen off the back of her chair.
He bends down (putting one hand on the table for support) to pick it up and feels a sharp pain run through his hand/arm. He looks up and she had stuck a fork into his hand and, while still on the cell phone, simply goes “oh it’s you” and continues her phone conversation. He found the waiter, paid for his half of the meal, and never looked back.
18. My Fight In Shining Armor
I was going on my first date with a dude. I told him I had a 3-hour window to hang out. He proceeded to suggest a coffee shop, but upon arrival told me he hated coffee and the atmosphere of coffee shops. Cool. So, I suggested an art museum or bowling. He said he brought no money because he doesn’t pay for dates on principle. That’s when I should have known this guy was bad news. But nope, I’m an idiot.
I offer to pay but he won’t have that either. So, I suggest a walk around a nearby lake. We have the most one-sided conversation of me asking questions and him giving one-word answers. When we got back to our cars (an hour later) I told him he didn’t really seem like he was into me and suggested we cut the “date” short.
The dude BLEW UP. “You said you had 3 hours and it’s only been an hour, you liar! You have 2 more hours! Our date is supposed to last 2 more hours.” Fine dude. It’s a beautiful day and if you want to do two more laps around the lake then by all means. I talked about any little tidbit that entered my brain, like the chick from HIMYM.
“Do you think when a porcupine walks through the woods his quills act like giant whiskers and he’s just constantly getting poked anytime he bumps into something? I ate a kiwi whole once and my mouth felt really fuzzy after, actually I ate a random leaf one time and my whole tongue swelled up let me tell you about that…”. I never heard from him again.
19. Mother Knows Best
It wasn’t my date who was creepy, but his mom. It was 1992, I’d barely turned 17, and I just had my first “kiss” that summer during a game of spin the bottle. At school, I noticed we had a new student in the class. He went up to me and said he thought I was cute. He gave me a ride home from school and then asked me out to a movie that weekend.
During the whole movie, he was all over me—lots of attempted kissing. After the movie, he wanted to park at a secluded section of the highway to “talk”. I quickly vetoed that idea. I may have been inexperienced, but I wasn’t dumb or naive. Instead, I suggested heading to the local family restaurant that my mom worked at; though she wasn’t working there that day.
Well, we ended up running into his parents while we were there. We chatted for a few minutes and then his mom leaned forward, took my hand, and said, “You know dear, we’re not going to be home for several hours if you want to go back to our house for some private time.” At that point, I developed my first migraine and had the boy take me right home. I did not date again for the rest of my senior year.
20. More Than A Little Off
One of my co-workers went on a date with a guy who worked with us. We had all been friendly with each other, so she told me that they were planning a date that night. To be honest, the guy creeped me out. She was 16, and he told everyone that he was 27 although he was actually 32 or so. But the creepy age gap was not the only thing on my mind.
He would say crazy things at random times. For the first month or so, it was mundane but normal. Toward the middle of the second month or so, he would just slip random thoughts into the conversation. He would say stuff like how he wished leprechauns were real so he could skin one, or that you could freeze a banana, stab someone with it and then just eat the weapon. That’s what we were dealing with.
We worked in a grocery store, so we’d often make conversation with each other. At one point, he’d be telling me about something mundane like the weather, his plans for the weekend, etc. Then, mid-sentence, he would pick up a box of Trix cereal and say, “I’d drown that rabbit in the milk and crunch his bones with that cereal” before putting it back on the shelf.
He once had to change the receipt roll, and in the middle of doing so, he told me that he could probably crush a cat’s skull with it. Honestly, the complete switch in what he was saying and how he was saying it was significantly more disconcerting than what he was actually saying. I had talked to the store managers about my concerns, but this was quite a while ago and nobody cared.
Anyway, I tried telling the girl who was going to go on a date with him that he was crazy dangerous. She told me later that she thought I was making things up because I wanted to date him myself. A few days or so later, she showed up and my jaw dropped. There were bruises on her hands, a couple of her fingers were taped together, and she was very obviously wearing heavy makeup.
Apparently, he had experienced some sort of episode. After picking her up, he proceeded to head straight out of town instead of to the center of town where they were supposed to be going. When she asked where they were going, he told her, “We’re going to the bridge because I need to finish you.” She tried getting out and he began beating her, screaming that they needed to get to the bridge.
After a couple of rounds of this, she escaped his car and he took off. The authorities were called, reports were filed, but the guy just vanished. When I lost contact with her a year or so later and she went off to college, he still hadn’t been found.
21. Fate Works In Mysterious Ways
I was living in Germany and had a date lined up with a German woman. We met at a restaurant, and within five minutes of sitting down, she said, “We really need to work on your German, but that’s okay, we’ve got our whole lives together for that.” First red flag. A few minutes after that, she started talking about her son, explaining that he lived with her parents because the court ordered it.
We hadn’t even discussed the restaurant menu yet, and this gal was dropping this kind of information. Second red flag. On the topic of her son, she decided to dive into the colorful history of the father. Basically, he knocked her up six years prior and rolled out. Mind you, I’d spoken about five sentences by that point because she was not giving me a chance to speak.
Suddenly, her phone rang and she answered it…at the table…in a really nice restaurant, less than 10 minutes into the date. She pulled the phone down and said to me, “I really need to take this call.” We still hadn’t ordered our food and I was just sitting there, by myself. Five minutes passed….10……20…..and then I finally ordered my food.
I got my food, ate it, and prepared to pay the bill. I assumed the girl wasn’t interested and just ghosted me—NOPE! After an hour, she came walking back to the table, crying her eyes out, saying that the call was from her baby daddy. He allegedly wanted to get back with her. She was upset because it was a tough decision. She really loved him but was also excited about a future with me.
At that point, I finally had enough and said it would probably be best if we didn’t talk again. I paid the bill, then left. After leaving the restaurant, she texted me at least every five minutes. It ranged from saying sorry to things like, “How could you do this to us? We were supposed to have such a good life together!” I ended up having to change my number because this went on for a week.
Here’s the good news: I swore that I was done dating for a while after this incident, but then I ran into a girl who was interested in dating me two weeks later and I gave it another shot. That was my last first date—we’ve been married for nine years now.
22. What Lies Beneath
This was 17 years ago and I’ll never forget it. I was 18 and worked with this guy who was 22. We worked at a big home loan company, and he asked me out for dinner after work one night. We were both working overtime that night until about 7 pm and I was hungry, so I agreed. I had interacted with him enough at work to feel comfortable getting into his car. I regretted it almost instantly.
Instead of driving to the restaurant, he said he wanted his mom to meet me. He drove to his house on a farm that was 45 minutes away. We got there and he introduced me to his mom, but guess what—she could care less. Then, he gave me a tour of his place in the dark, showing me where they kept the pigs, the horses, and the rest of the animals.
I was uncomfortable at this point, but also naive and 18, so I made some small talk: “It must have been so cool to grow up out here. I would have loved this as a kid!” He then said something like, “Yeah it was, but I had a problem.” He then folded his arms and refused to make eye contact with me. Me being young and still naive, I asked him what he meant.
That’s when he told me a terrifying confession. He said he was a very angry teenager and that he used to kill the rats and mice on the farm. I then replied, “Oh, you mean like with a BB gun? That’s not a big deal.” Nope, not that. He told me that he used to trap them and then stab them while they were in the traps with his pocketknife.
Then he said his “problem” progressed and that he “ended up” stabbing the neighbors’ cat. Apparently, it got so bad that he did it to one of his own pigs. His mom found the pig and that’s when he knew he had to stop the behavior. At that point, I was majorly disturbed and wanted to leave. I was starting to realize that everything he was telling me was a “psycho in the making” kind of behavior.
I reassured him that his problem wasn’t that weir” and that I wouldn’t tell anyone about what he had said. I started to get really hungry and wanted to get back to my car at work before they closed the gates. It was a big office building complex that shut its gates at 9 pm. So he drove us back and we ate dinner at a popular burger place as per my request.
Afterward, he took me to my car in the empty parking lot at work. As soon as he pulled up, I thanked him for dinner and quickly got out of his car. I rushed into my car before he could even get out a goodbye. I never went out with him again. I tried my best to avoid him at work without being rude or making him angry, and luckily he got promoted to a different department in another building a couple of weeks later.
23. Won’t Somebody Think Of The Children?
I got catfished by the craziest woman I’ve ever met. I don’t mean like, “Ohh, that woman is crazy,” I mean, every time she reached into her bag, I thought she was about to pull a weapon out by the way she was frantically rummaging through it. She seemed off from the jump from the moment we met. At one point, she looked at me and said, “Do you ever wonder what your kids will look like?”
I replied, “I already know. My daughter is right there and she’s perfect.” The crazy lady continued, “No, I meant our kids, since we are going to get married and have a house in Texas.” I had literally just matched with her on Tinder the day prior. We never once spoke of anything more than normal conversation topics on the app. Nothing in the slightest related to either topic.
I faked a phone call from work, got in uniform, and told her she needed to leave. I waited for her to leave, then drove around the block.
24. The High Life
I once agreed to go on a date with one of my stepdad’s clients, who was the son of a very rich luxury yacht builder in the country. The company is known for its extremely strict rules, particularly for women, some of which border on human rights violations. He took me bowling and rented out the alleys on either side of us as well so we’d have some privacy.
He was telling me about the lessons he’d learned from someone who’d coached several world champions in bowling. Afterward, he showed me pictures of his house—his bedroom alone was the size of a swimming pool, and his garden was a literal zoo with several monkey species as pets. He then started telling me a bit about his family.
He gave me a few little interesting details about each of them, and then it took a dark turn. He got to his older brother’s wife, and it was pretty clear she was the main subject of the conversation. He told me his brother had studied in the UK as he did, met a nice English girl like me (even though I’m Irish, not English), and fallen in love.
His brother had taken her back to his home and asked her to marry him, but with the condition that she move into his parents’ house with him and live by their strict rules. She was reluctant at first but eventually agreed to it. Then he went on to say: “And her life there is so good that she never even wants to leave the house! She stays home and has babies and wears Prada and looks at the horses. She’s so happy.”
He ended with, “Who would ever even want to leave a house like my family’s house?” He started asking me if I’d ever like to go there and meet his family. Alarm bells were going off at a rapid rate in my head. When I got home and told my stepdad, he immediately took the guy off his client list and we haven’t seen him since.
25. Full Of Hot Air
I ran into a guy from high school years after graduation and he invited me to meet up with some of our other friends. Well, when I got to the restaurant, there was nobody else there, just him. Yup. I was ambushed into an unwanted date. To make it worse, he had told the wait staff we were on a date and to take their time.
TWO HOURS LATER, I was finally able to leave. He walked me to my car, even though I asked him not to. When I went to get in my car, he blocked me and he leaned in for a kiss, which I was not down with at all. It was a dark parking lot and there was nobody around. Super sketchy. I wish I could say that was the worst of it, but it all unraveled from there.
Apparently, something at dinner did not agree with him. I turned my head to the side and went for a friendly hug to dodge his attempted kiss. That’s when his bowels UNLOADED. It was the loudest and gnarliest fart I have ever heard. It happened the second the hug commenced and he didn’t let go until it was done. THEN he tried to kiss me again.
I deflected into another awkward hug AND HE DID IT AGAIN. All in all, it went on for at least 30 to 45 seconds. In the end, he made eye contact and said, “let’s do this again.” Hard pass.
26. Take A Hint, Buddy
A few months ago, I matched with a guy on Tinder. Things seemed to be going well over chat so we ended up meeting for a date. As soon as we met, I had a bad feeling about him. I just had a vibe we weren’t going to progress any further. He seemed a bit off and not as friendly as he appeared online. Still, I thought I might as well have a meal and chalk it down to experience if it didn’t pan out.
During the course of the meal, alarm bells began to go off. He started referring to women as “stupid and pointless” and “only good for one thing.” I began to get really uncomfortable and was trying to think of a good excuse to leave. Of course, I got naturally defensive and said talking about women like that was derogatory.
He then started to complain that there were vegetables in his burger—referring to the lettuce—and he proceeded to pick it out. He called the waitress who took our order a “dumb witch” because he specifically said no vegetables in his meal. I finally said that I had to go because, honestly, at that point, I felt like shoving the lettuce in his fat misogynist face.
To say I ran as fast I could to my car is an understatement. As soon as I got in my car, I ended up un-matching from him and I blocked his cell phone number. Later on, I still received a chilling text from another number. He said, “Hey, it’s Brad from Tinder. I know pretty much all I need to know about you, so let’s sleep together, okay?”
Like, what the heck. It sounded so creepy; like he was analyzing me to see if I was suitable to sleep with. Also, he obviously knew I blocked him, so why bother sending anything at all? I didn’t reply to him, obviously, and I blocked that number.
27. Kiss Kiss, Bang Bang
He showed me pictures of his kids. “Here is Tommy, and the other one is my fat kid.” I thought I misunderstood and made him repeat. Indeed, he called the other boy “his fat kid”…after I heard that, I told him I had to go. He insisted on taking me to my car, and while walking, he asked me, “How are you in bed?” I stopped in my tracks and had a good look at him.
I was 45 then, which is the prime age for a lady. To be honest, I felt like a million dollars. I felt beautiful. He was much older than what he had told me beforehand, and his prime happened 30 years ago. He was weathered with a bad haircut and he smelled bad. He was also so, so bitter with life. I simply replied that he would never find out.
As I was opening the door of my car, he tried to kiss me, but since I was taller than him, he kissed my shoulder. I closed the door on him and started the car—which is when the cherry on top happened. He put his lips on my windshield to kiss it. Imagine a grown man doing this, with a big smack sound. I was sitting in my car watching this happen, and his eyes were trying so desperately to be sexy.
My hands were on the steering wheel, touching the wipers/washer thing, and I played with the idea of splashing him for few seconds. I remember my finger touching the control…but I ended up not doing it. I actually felt pity for him. In the end, I had a funny story to tell, but he had a very embarrassing one to take home with him.
28. Poking Holes In That Dream
I went out with a girl I met through OkCupid once. She was a student in a nearby city, so I drove out there and we went on a very lackluster date. At the end, she invited me back to her place, and I accepted. When we got there, we ran into her roommate as she was leaving. The roomie told us to have fun and that she wouldn’t be back for a while.
I went into the girl’s room and we chatted a bit. Then, things quickly turned intimate. Somehow, she segued into her telling me how she and her friend once went into the campus’ sexual wellness center and used a needle to poke holes in all the condoms they had set out when no one was looking. She told the incident to me like it was supposed to be a funny story.
Afterward, she said she was going to run to the bathroom to get some condoms so we could get to business. Needless to say, we did not get it on that day. I told her something came up while she was on the toilet and left. Obviously, I never saw her again.
29. I Was Rooting For You
“Look, this has to go well. Both of my brothers’ wives are pregnant with their second children. Do not let me down.” He said that to me within three minutes of sitting down. I thought it was a joke at first and tried to awkwardly laugh it off, but the tone of his voice was something I’d never heard before. He also didn’t blink much and he had the most intense, intimidating stare.
It was like he was trying to make me break down and confess my darkest secrets right there at the table. Some other things were said, mainly pertaining to his occupation, that made the hairs on the back of my neck stand up. Looking back now, I feel like there’s a 99% chance he was doing unlawful stuff at his job, and whatever he was doing would have impacted a ton of people for life.
30. I Wash My Hands Of You
On my first date with this girl at a restaurant, I excused myself to use the bathroom. She got up and followed me, making flirtatious remarks along the way. I thought nothing of it, assuming she needed to use the restroom as well and was just making small talk. I walked inside the men’s restroom…and she walked straight in with me. Okay.
So I turned to her and said, “Um, I actually do need to use the restroom.” “Oh, I’ll watch.” “No…just no.” I was not able to pee in public for a while after that.
31. A Blast From The Past
About two years ago, I divorced my wife after she cheated with a guy she met at my mother’s funeral. Six months after the divorce, I’m on my first date with a girl named Heidi. She wanted to stop by a local tavern that was hosting a charity benefit. We did…Worst decision ever. I walk in the front door and immediately I am face to face with the guy who screwed my wife.
He and I grew up as friends but lost touch until he came to mom’s funeral. He attempted to say something to me, and I immediately cut him off and threatened him rather harshly. He left. I spent the next 30 minutes explaining what just happened to her. She said I should have punched him…
32. Card-Carrying Monster
It was a horrible date. This guy was incredibly misogynistic, talking bad about his ex-wife and saying that most women are bad mothers. He was saying why he doesn’t date within his old-school, Romanian gypsy community is because the women lay like fish during intimacy. He even went as far as to say that he thought American women were more fun in the sack.
I know, I know…I clearly didn’t vet him enough before hanging out with him. But then he outdid even himself. He took my credit card out of my purse when I wasn’t looking. Luckily, on the way home, I stopped for coffee and noticed it was missing. I froze the account that very second and searched everywhere for three days, hoping I was wrong.
But I knew deep down that I had been played. I just got that gut feeling. I never did find that card.
33. My Bloody Valentine
I’m a waitress at a nice restaurant. One of our favorite regular customers brought in her boyfriend for the first time, and in her excitement, she bumped into a table and knocked someone’s cup off. This wasn’t bad at first, but it turned awful in an instant. In her haste to pick up the cup, she hit her head on the corner of the metal table and cut her forehead open.
We cleaned her up and gave them a stack of free food cards because she’s awesome and we love her.
34. Delayed Disappointment
When I was in high school, I went on a date with a friend of a friend. We saw a movie, then went out for dinner. I was nervous and awkward, and it ended without much fanfare. The date went okay, and there wasn’t a second one. But that’s not the bad part. About a month later, I went to a party at our mutual friend’s house.
I saw her there and was afraid it might be a little awkward. About an hour into the party, she came up and started talking to our mutual friend while I was standing nearby. After a few minutes of talking, the girl I had gone on a less-than-awesome date with came up and introduced herself to me. On the bright side, at least it wasn’t a memorably bad date…for her.
35. Musical Urinals
We went to a movie. During the movie, she got up to go to the bathroom. After she left, I thought I could run to the bathroom myself, and be back before her (for some reason, I thought it would be rude to leave her alone). When I came back to our seats, she was already there but I didn’t give it much thought.
I hung out at her place for a bit afterward, gave her a kiss goodnight, and went home thinking that I just had a pretty nice date. A week later, after she wouldn’t return any of my calls, I asked our mutual friend who introduced us what the deal was. Turns out that when I went to the bathroom, I accidentally walked into the women’s room.
I peed in the stall next to her, and she recognized the boots I was wearing. She was totally freaked out. When I finally got a hold of her and tried to explain myself, she told me she was moving to Turkey to get back together with her ex-boyfriend.
36. Beauty Is Only Skin Deep
So I met this girl on the Internet who seemed really nice and down-to-earth. We had a lot in common, including our hobbies and stuff like that, so I thought we would actually hit it off. We agreed to meet up in person at a Kaladi Brothers coffee place. Now, bear in mind that I’m not super attractive, so up to this point, she hadn’t seen any pictures of me.
Instead, we had pre-arranged recognition signals. She walked in the door and I spotted her by her clothing, so I instantly started waving. She immediately got this sort of uncertain look on her face. Then, she walked over and said, “Sam?” When I said yes, her response completely crushed me. She just said, “Haha…no” and walked out. It just sucked to realize that my looks relegate me to dating the catastrophically nearsighted.
37. A Slight Change Of Plans
I had been dating this girl for several years. Let’s call her “Ann.” We met while working at the same company and things were going really well between us. So well, in fact, that I thought that it was time to pop the question. So, after asking her dad for permission, I planned a whole romantic evening for her, which was going to culminate in me pulling out a beautiful ring after dinner at a very nice restaurant and surprising her with my proposal.
So the big day finally came. Ann looked crazy nervous throughout the whole dinner, but I assumed she just knew what was coming and was feeling anxious in anticipation. As I said, things had been going really well between us. After the main course and before dessert, I got down on one knee in the middle of the restaurant and proposed to her.
Then she said no. That was bad enough, but when she told me why, I nearly exploded. Apparently, she had been secretly dating my co-worker for several months and was planning on breaking up with me, which she proceeded to do right then and there. In front of the whole restaurant. And then she left. The waiter gave me a free dessert.
It was still pretty brutal.
38. My Own Worst Enemy
At the time I started dating my girlfriend, I liked to go on long walks to clear my head. My favorite place to stroll was through the woods. I always went out for a walk at nighttime, so I had gotten used to walking through the woods at night and I really enjoyed it. I still do. There’s something serene and peaceful there in the darkness and silence.
Anyway, we had our first date. After a relatively successful evening, watching Yes Man in the cinema and chilling out in the arcade, I opted to walk her home. She accepted! I offered to take her on my usual route, and I told her it was through the woods. I wanted to show her why I liked it so much. I had no idea how I was coming across.
I obviously sounded like a shady, shady dude. She still doesn’t let me hear the end of it. “Jon, on our first date you tried to take me through the woods at midnight…” Fair enough. Even I see her point. What on Earth was I thinking? We’re still together, though. She must really like me…
39. There’s No Accounting For Taste
I’m a server. I had some guy on a date who could not get the concept of ravioli. He kept asking if we hollowed out a spaghetti (his words) and stuffed it with lobster. I said no, but confirmed that we did use pasta. He kept reiterating that he wanted pasta. Then, it dawned on me. “Sir, do you think that spaghetti is the Italian word for pasta?”
I finally got him down for an order of lobster ravioli, even though he still seemed unaware of what he was actually ordering. After he got his food and ate one of the ravioli, he said to me, like I was the dumbest fool on the planet, “Bro, all you had to do was tell me that they were Boyardee’s. I know what those are.” His date was clearly unimpressed.
40. A Song In The Key Of YIKES
I told this guy I played the piano, and half an hour into the date, he said: “If I wanted you to always remember me, I’d break your ring fingers. You know, ’cause they don’t heal well and then you’d always think of me when playing.” Suffice it to say, I left the restaurant fairly quickly after that and never returned his (numerous) calls from then on.
41. Space-ially Challenged
I dated a girl for around four months a few years back. One day, we were chilling at my house, and I asked her if she wanted to watch an episode of Brian Cox’s documentary Wonders of the Universe. She declined. When she said why, my jaw hit the floor. Apparently, she didn’t believe in space. She was 100% convinced that the sky was all there was.
42. The Boy Is Mine
While she was driving us back home from the restaurant, she started saying things like, “You know, you’re in my car now, so I technically can take you wherever I want. You’re like my captive.” I laughed the first time she mentioned it because I’m into dark humor, but when she kept going on with it, it started to really give me the creeps.
Little did she know that once I got out of the car, that would be the last time she’d ever see me.
43. Teenage Dream
My first date was way beck when I was in high school. We went to see our high school’s version of American Idol. He was 15 minutes late and I had to save us seats, so I ended up buying his ticket. When he finally got in, he clenched my hand in a sweaty grip throughout the entire night, while shaking nervously (it was cute, whatever).
He kept making awkward conversation and tried to make me laugh. After, we walked out of the building to where his mom was picking him up. He kissed me on the forehead, hard. Oh, high school.
44. Oh, Baby
On our very first date, she showed me a long list on her phone of at least 60 to 70 baby names for her future children. She joked about having baby fever constantly…but it was obviously not a joke. Weirdest and maybe worst of all, they were all really country-bumpkin names like “Brekken” and “Gatlin”, which somehow made it more unpalatable for me. We were both 21 years old.
45. Do You Want To Play A Game?
I went out with a girl one night and after dinner, she drove me up into the mountains. Since I was new to the area, she wanted to show me around town. After a while, when there were no more lights, she started talking about…serial killers. I still remember her saying, “I used to think about getting away with stuff like that sometimes.” Uh…yeah, I didn’t go out with her again.
46. What A Catch
I went on a Tinder date to the movies when I was 18. He picked me up in his truck and played terribly loud, depressing music. In the theater, he was on his phone swiping on Tinder the whole time, then, at some point, he leaned over and told me that I was lucky to be out with him because all these other girls wanted to be with him. YIKES. My roommate picked me up when I excused myself to the bathroom.
47. A Surprise In-Store
We went on an early evening coffee date and it was going pretty well, so we grabbed dinner together afterward. Towards the end of it, he said, “You know, I could break your heart so easily. I could absolutely destroy you. I could make you fall in love with me and then just…Disappear.” I laughed uncomfortably, but the conversation basically petered out after that.
When we finished eating, he asked if he could see me again. I said, “Uh, you know… Maybe….” And then got my butt outta there. Also, at one point, he asked me for some “sugar” (a kiss) while we were chatting in his car, to which I firmly said no. He then replied, “I guess some girls are pretty and like to be called smart, and some are smart and like to be called pretty. Which are you?”
There were so many things wrong with his attitude. Looking back, I can’t believe I stayed out so long, but I guess the weirdness didn’t start until after we got dinner. I kept just thinking maybe he had an odd sense of humor until he dropped the “destroy you” line. After that, I was out.
48. Daddy Issues
“My son is gonna love having you around.” Lady, we talked twice on Tinder and I’ve only known you for five minutes. Ease up on the step-daddy talk. Full disclosure, not long after this ill-fated date, I met a nice woman on Tinder who also happened to have three children. I adopted all three not long after we married. So, yeah.
49. Pillow Talk
This guy wasn’t talking at all. I only brought a few talking points with me because normally guys tend to talk the whole time. I didn’t have anything else to say, so I asked him to start talking. He replied, “What I want to talk about can’t be said in public.” When I ended the date, he thought we were going to go to my place to “talk” some more, but I told him no.
I got in my car, noted what car he got into, and took a few breaths to calm down. I looked around and his car was still there. I waited 30 minutes before he left the parking lot and stayed another 15 minutes before I left, just to be sure he was really gone.
50. Mrs. Dressup
On our first date, we went back to her place. While giving me the tour, she pulled a beautiful wedding dress out of a closet and said, “When we get married, I can wear this dress,” while holding it up to her body. To be completely honest, I didn’t react that well…I just said, “Aww, put it on and I can take it off.” Then I never called her again. But that’s not the end of the story.
Three weeks later, she called me at midnight to tell me; “I know you have people watching me. I can’t go to work or school with your people sitting across the street all day and night.” It actually made me feel worse about my decision to sleep with her since she clearly needed help, but it also confirmed my suspicions about her overall vibe.
51. True Romantic
This dude and I kept randomly being on the same bus. We would never talk, but sometimes we’d make eye contact. After a few months in this cycle, we got off at the main bus hub. He approached me and asked me to dinner. There was a teriyaki place right across the street, so we went there and had a good conversation. I had a good time…until it came to the end of the date.
When the time came to separate ways, he brought up his hand and cupped my cheek. He just sort of left it there in silence…then slowly grazed his fingers down along my face as he pulled away. I did not call him.
52. Photo Finish
This was in the early ’00s when I agreed to go on a date with a persistent co-worker at Target. He showed up at my house with a giant bouquet of flowers. My parents invited him in to check him out and they spoke with him for a bit. It started to get strange at that point. Everything he was saying about his background didn’t really check out—he said he was a volunteer firefighter in a year when he would’ve been like 10 years old.
Then, all of a sudden, he pulled out a disposable camera. When my mom asked him what it was for, he said, “Your daughter is going on vacation for a week and I want a picture to remember her by.” Then, like from a dark comedy, we heard the click of the shutter. I faked being suddenly sick and my mom told him I wasn’t feeling well. Luckily, it was only a summer job, so I didn’t have to see him after that.
53. The Follies Of Youth
We were 14. At the time, I didn’t know what the heck to do about women…so I took this one girl to Subway on Valentine’s Day for some sandwiches. It was freezing out, with five feet of snow. She brought her friend for the whole meal, which was kind of annoying, but whatever. After we ate, we walked back and on the way, her friend kicked a piece of plastic.
For some stupid reason, I don’t know if it was stress or whatever, I thought it’d be awesome to jump up and down on this piece of plastic while grunting. That’s what I did to try and impress my date. I destroyed a helpless piece of plastic, then kicked it onto the road. I still cringe to this day thinking about it. It was very violent. Yet for some reason, this chick still dug me.
She talked about how cold her hands were the whole way back. At the time, having so little experience, I didn’t understand the signals of her wanting to hold my hand. We got back to school, said our goodbyes, and we were forever awkward around each other for the rest of high school.
54. A Special Surprise
On Valentine’s Day, My friend worked a 14-hour shift in a restaurant and then wanted to meet up with her boyfriend afterward to give him his V-Day gift. He gave her an address, but when she showed up, she came to a horrific realization. It was a strip club. He hadn’t told her this. Needless to say, she wasn’t happy. She went inside, V-Day balloons and gift in hand, located him, dropped off his gift, and Ubered back home alone. Poor girl.
55. Straight Out Of A Movie
He insisted he drive me to the movie theater, which meant he would have to drive to my town 45 minutes away, then back to his town to go to the cinema, then back to my town to drop me off. I told him I was fully capable of driving myself to save the multiple trips. When I adamantly refused a ride, he still drove to my town, bought me a coffee, and insisted I go in his car.
I still said no, citing the fact that it would be dangerous for me to get into a vehicle with a person I didn’t know, and I drove myself to the cinema where I had a friend meet me for the movie. The guy still came with us and even paid for me despite me telling him that I didn’t think it was a good idea. I never spoke to him again and blocked his number.
56. Animal Instincts
He described at length how men were all naturally as violent as the men in the movie A Clockwork Orange. He explained that they actively suppress their rages in order to fit in with society…He also invited me to a pub and proceeded to drink water while buying me seemingly bottomless G&Ts. Needless to say, I yeeted out of there real quick.
57. Mr. Big
My mom was an online dating pioneer. She was really interested in finding “someone special.” She agreed to meet this one guy for dinner (first mistake) and she went in to be seated prior to him arriving. When he came in, the waitress brought the menus. He set down his menu, and the first words he spoke to my mom were horrific.
He asked her if she knew anyone who had an enlargement surgery, uh, down there. He then went on to explain that he had flown cross-country for this operation and that it had “gone wrong.” He went into great specifics about just how wrong, too. My mother excused herself to the ladies’ room and went out the back door. We still laugh out loud when she tells us that story.
58. No Means No
It wasn’t a date, but he’d convinced himself it was. It was just a mutual commiseration over the two of us not getting to go on a company trip. We were at a bar near the shop and coincidently, it was near his house too, so I parked there to avoid paid parking. When I got out of my car, he asked me to come inside to “pre-game” and I got weird vibes.
I’d turned him down twice before and something about the scenario flicked on a switch. I lied and said I’d rather have only one drink at the bar as I was going to drive home later. He then said, “Oh! I’ve got sealed drinks in the fridge and my roommates are home, don’t worry.” After he said that, I got EXTRA worried. Now, I’ll admit to being a pretty paranoid person.
I went to school to be an officer and am an insufferable party mom. I don’t drink booze out of open spirit bottles. I also don’t go into other people’s homes without at least one other close friend with me. Both are rules that were born out of necessity from experience. I’ll admit the odds were stacked against him on that one.
The thing that first set me off, though, was the offer to come inside. I’d already turned down his advances twice before and he was proving himself to be disrespectful of my boundaries. He was super awkward, however, so I was willing to give friendship a chance. That’s why I even considered going to the bar with him in the first place.
I had no idea at the time that anyone else was home, and it was too intimate an offer to be sure he’d be respectful of my space in his own home. The nail in the coffin was when told him I just wanted one drink at the bar—he simply responded with another push about the “sealed drinks.” It just affirmed to me that yeah, he couldn’t take no for an answer, and I was pretty sure he didn’t intend to leave after we went inside.
One day after this incident, we were all on a bus heading to a meeting and he sat next to me even though I told him there were plenty of other seats. I stared out the window and ignored him the whole time. When we arrived, he asked me how my nap was. I said I wasn’t sleeping and he said, “No, I can tell when you’re sleeping.”
For what it’s worth, he was attractive. Probably an 8/10. I just wasn’t interested like that. Before I turned him down the second time, I actually liked him a lot. The first time I was clear and said no, but we just carried on as we were. The second rejection was a “Dude I already said no, this time listen to me because I mean it.” Apparently, that wasn’t good enough.
I quit shortly after the bus incident because my boss refused to separate us or do anything about it.
59. Constant Vigilance
This was a distinctly creepy date I had. My first Tinder match got me to sneak out of my house at midnight. He led us into the hills and at one point he said, “What would you do if something attacked us?” He just stared right at me. Keep in mind it was a cold October night and I was in a sweater, sandals, and I had no weapon to defend myself.
I can’t remember what I said back, but he then laughed and started talking more about different scenarios like running out of gas or getting attacked by different animals along the way. He then mentioned he had a katana in his trunk, and at that point, I really wanted to go the heck home. Needless to say, I never went out with him again.
60. Baby Mama Drama
He told me I was getting old and needed to get married so I could have kids and my grandparents could meet them. At that point, I was 25 and he was 24. The entire conversation was him waving a lot of red flags about wanting a baby mama and partner who “hadn’t gotten around.” Needless to say, there was no second date. Gross.
61. The Eye Of The Beholder
I was about 17 or 18 years old when this happened. We watched a movie together at the cinema. Afterward, in the parking lot, he licked my eye. LICKED MY EYE! Then he became all weird and possessive because he couldn’t get the hint that I didn’t like him. He kept texting me at 2 am to ask if I was at work (I worked in a small rest stop area in the middle of nowhere and had to be at work around 3 am on most days). He also kept demanding that I tell him where I was at all times.
I eventually told him to go screw himself. I quit responding to him entirely.
62. Come Over To The Dark Side
My mom, who is a practicing Protestant, went on a blind date once sometime before she met my dad. The guy she was set up with claimed to be a Satanist. Not an edgy atheist with extra steps, but ultimately a harmless Satanist…I’m talking about someone who legitimately worships the devil. Yeah, that date went about as well as could be expected.
Oh, and the best part? The guy was faking being a devil-worshipper. Apparently, he thought it would somehow impress her.
63. Just My Type
She told me that she was not desperate and did not necessarily want a boyfriend. She then listed a bunch of people who she had dated. At some point, she started to tell me that she has now lowered her standards and that she didn’t care if her next boyfriend was tall, short, fat, thin, or even red-haired. I am short, fat, and red-haired.
64. Jekyll And Hyde
A guy I went on a date with had super scary road rage when he was driving us to a restaurant. I mean veins bulging in his neck, spittle flying; the works. He kept RAGE screaming as I clung to the door handle to get as far away from him as I could get. I kept wondering if he was going to pull out a gun and shoot someone, while also mentally debating if I should jump out of the car at the speed we were going.
Then, at the restaurant, he was pure Mr. Charming; all concerned about why I was suddenly so quiet.
65. I Put A Spell On You
“Gerard Butler mustn’t find out about this. He gets very angry about my affairs.” Not exactly a date, but she told me this while we were hitting it off at a party. She then explained to me how she married him (Gerard Butler) through witchcraft and showed me her “Book of Shadows,” which was actually just a purple file folder with some badly drawn runes on it.
66. Stirring Things Up
One time, I was the bad date. I went out for drinks and tacos with a sweet guy from Tinder. It was going pretty well, so when he asked if I wanted to walk home and hang with his roommates, I happily obliged. When we arrived, his roomies were drinking screwdrivers. They asked if I wanted a glass—I said sure, but the thing is, I have a strange compulsion to stir any mixed drink thoroughly every time.
I couldn’t drink from the cup until it was stirred. I walked into the dimly-lit kitchen and grabbed the first utensil I saw on the drying rack, which happened to be a steak knife. Walking back to the living room, everyone was looking at me like I had turned into a ghost. They straight-up thought I was going to slay everyone in the house with a steak knife until I started stirring my drink.
67. Easy There, Rider
This is a Tinder first date story: I knew early on from the conversation that this guy wasn’t going to be “the one,” but he was safe and the sushi was good. At some point, he got into how he loved going on road trips on his motorcycle. I mentioned that I liked road trips too, just to keep up with the conversation.
Date: We should get you a motorcycle soon then!
Date: Yeah, and we can get those helmet radios so we can talk while we ride…say cute stuff like “I love you” and whatever.
Weirdly enough, the conversation fizzled after that, and I had to go—I had purposefully made it a lunch date so that I’d have an out. Dating tip: Always go Dutch, and always drive yourself on the first date.
68. Bottoming Out
Oh, I’ve got a good one. Once, I was on a first date with a guy I met on Tinder. He picked me up for dinner and then we went bar hopping afterward. He grabbed my butt while we were walking down the street. I told him to kindly NOT grab my butt, and he said, “It’s my butt now.” I Ubered home so fast and vowed to always take my own car on a first date.
69. Home Is Where The Creeps Aren’t
He told me, “I know you’re trying to get sober, but I still got you a drink. One more won’t hurt.” Then, when I got up and grabbed my bag, he said, “Why are you leaving? I paid for that, you need to drink it. I’ll walk you home too—I want to know where you live for next time.” Thank God for the security team at the student halls. They stopped him at the gate when I said he was following me.
He knew the halls, but there were 500+ rooms that he would have to get entry to in order to find me. Thankfully, I never saw him again, but he regularly texted me angry messages about not going on another date with him…
70. Giving “Ghosting” A Whole New Meaning
I went out on a date with a guy whose real name was, I kid you not, the same name as a beloved children’s book character. Midway through the evening, he told me he had an ex and she was terrified of his ghost when she slept over. He then told me that eventually, I’d sleep with him, and when I did, he’d sit up in a chair watching me all night so the ghost wouldn’t get me.
71. Did I Get The Gig?
About 10 minutes before we were due to meet, she called and said she had spotted a few friends at the bar. She said she would probably be with them when I got there. That sounded both fine and normal; if a bit intimidating for a first date. But that’s not what happened at all. Instead, it was her and four other strangers crammed into one side of a booth. They all asked me to sit on the other side.
They proceeded to give me an interview-like panel discussion about dating their friend. I could have maybe gone along with it if my date at least seemed embarrassed, but no, she was fully into it. After a grueling few minutes, I excused myself to get a drink but just went home instead.
72. No Such Thing As A Free Meal
When I first moved to a new city, I managed to catch a Tinder date. The date itself was just fine and we hit it off. Near the end, though, she made a show about wanting to pay Dutch. Then, when I insisted I was paying, she proceeded to order an extra $40 worth of stuff to go. I immediately told the waiter that the stuff she ordered was going on her tab, and she made a huge stink about me going back on my word.
73. Baring His Soul
I lost my virginity to a one-night stand when I was 19. We were in my bedroom which faced the apartment next door, so I could see the windows of the people in the opposite apartment. After we had slept together, we were chatting about my view and how I kept my blinds closed most of the time.
Then with a straight face, he said, “At least you can watch people change.” I waited for him to eventually laugh or something to suggest he was joking, but it never happened…
74. Honesty Is The Best Policy
He told me about all the misdemeanors he committed in his past, about his alcoholism and substance use, and his estrangement from his family. He got everything out for me to hear on the first date, while we sat across from each other sipping coffees. I was actually very impressed with his honesty and openness, though a little taken aback.
It struck me after being with many different guys who had lied about important things that even though this wasn’t the typical kind of guy I would’ve continued dating, I still really felt he was a good person at heart. He had gotten through a twelve-step rehab program and also made his societal amends while working in a job he liked.
We went on a second date and it was then that I realized I could really fall for him. Two years after that, we got engaged.
75. Nice Gams
On our first date, he complimented me in a very intimate setting: “Your legs are so pretty.” I was like “Aww,” and he followed with, “Can I have them?” It turned out, it was just bad humor and an anxious line. He was a complete dork. We dated for a year or so, and he’s a good guy; all things told. Plus, I still have my legs. I call it a win.
76. Cabin Girl
This girl basically interviewed me while she kept ordering more drinks for me. Then, in the end, she asked if I wanted to be her “winter boyfriend” and spend time with her and her parents at a cabin in Vermont. The catch was that I had to commit to the whole season. “Oh, but we will have our own separate cabin and we will sleep together,” she assured me.
I hadn’t even kissed her yet and she still casually dropped that we’d be friends with benefits for a few months. As most red-blooded men would do, though, I took her up on her offer. Her parents were really cool, she was super hot, and I got a free stay in an awesome cabin plus snowboarding for the whole season. She definitely had some form of social disorder, though—she couldn’t make any connections with people, and she didn’t have a single friend.
77. Better Put A Ring On It
I worked at a fine-dining restaurant years ago. A middle-aged guy came up to me, handed me a gorgeous sapphire and diamond ring—just gorgeous—and asked me to have the pastry chef include it with his companion’s dessert. The chef found beautiful blooms to decorate her dessert plate with and he placed the ring in the middle of one.
She saw the ring, took it out of the flower, and placed it on the table. Then, she picked up her fork and started to eat her dessert without saying anything at all. The ring must have been an extravagant “I screwed up” apology on his part and she was having NONE of it. I was tempted to say, “If she doesn’t want the ring, I’ll take it!”
78. Read The Room
He drove me out to the desert for stargazing and a bonfire thing. Yes, I know it was a dangerous first date, but I was stupid and young. Once we found a good spot, he turned the car off and told me, “Now this is where I kill you.” He said it with a smile and started laughing. I’m just glad he was just joking but it doesn’t make it less creepy.
79. Absence Makes The Heart Grow Fonder
My friends and I met up at this big food court to hang out. It just happened to be Valentine’s Day. Well, one of my friends got there an hour early and saw this one dude with a bouquet of flowers and a giant teddy bear. Almost FIVE HOURS later, we came back to the food court for lunch and the guy was still there with no date.
We watched him make a call, throw the flowers to the ground, pick them back up, and eventually leave.
80. Public Displays Of Affection
My wife and I went to The Cheesecake Factory for lunch on Valentine’s Day in a bid to avoid the crowds. Next to us, a dude got down on one knee and proposed (yes, in a Cheesecake Factory). The waitress was filming it and people were watching. The girl saw the ring and started crying. He smiled, and it all looked good… until the other shoe dropped, hard.
When my wife and I left 20 minutes later, she was still crying, covering her face, and he wasn’t smiling anymore. I couldn’t hear well enough to know what they were talking about, but they kept speaking in low voices. It didn’t look good.
81. The Grim Escape
I went on a blind date at the time and the girl was less than perfect. She was loud, constantly babbling with a stupid laugh, and had tasteless clothes, She mentioned she was taking her dog to get spayed and, in a moment of inspiration, I said, “Oh, I just let mine have puppies and then suffocate them in a plastic bag.” I spent the rest of the evening playing StarCraft.
82. The Wet Bar
I bartend. I was assuming this one couple was on a date as they had just ordered their food. 10 minutes into their date, I saw the girl take a drink—a full pint—and throw it on the guy. It hit the people behind him, the walls, and the floor. She immediately walked out, almost in tears. The guy’s face as he just sat there soaked was indescribable.
It was the most movie-like break-up I’d ever seen happen in real life.
83. Our Interests Align
I was set up on a blind date with an aerobics instructor. For what it’s worth, I’m tall, lean, and fit myself. I’d recently smashed my Honda sedan and was temporarily driving an old pickup instead. She spent the date telling me how much better she could do than me. The feeling was mutual.
84. You Don’t Get By With A Little Help From Your Friends
I have a bit of a thing for nerds, so awkward dates kind of come with the territory. The worst was when I went out with this one guy. Even though it was really casual, he was so nervous that he brought his roommate so he wouldn’t have to go alone. He was 28. The sad part is that I would’ve stuck around were it not for Roomie McThirdWheel.
85. A Key Moment
He freaking took my keys while I was out of the room and took off into the night. We had an hours-long standoff where he wouldn’t answer my calls or texts. I stood by his truck which was parked a few blocks away, just to make sure that he didn’t leave with them. Eventually, he dropped them off in my car and I got a ride home from the authorities. Honestly one of the scariest episodes of my life.
86. Animal Attraction
My date was a vegan, but she didn’t tell me that. We had our first date and we went to a Thai restaurant. As we were ordering drinks, she decided to reveal to me that she was vegan. She refused to eat anything there. I was annoyed, but I still tried to salvage the date. We talked for a while over drinks, and then she took me to a vegan cafe…where she lectured me about how terrible people treat animals. Never saw her again.
87. Silence Is Golden
I went to a movie with a girl when I was still really young. We saw Ever After (her choice). One of the trailers was for Star Wars. Being a massive nerd and not yet knowing that EP 1 would suck, 100% of my attention was on the trailer. During the trailer, she asked me a question. My response? “SHHHH!” Nice one, idiot younger me…
88. Rollercoaster Ride
I went on a double-date with a girl from college and two nerds. The girl who had asked me out was kind of a swervy driver and didn’t seem to have driven much before that night. Literally, five seconds before pulling into our parking space, the girl in the backseat threw up mid-sentence. She threw up all over her feet and clothes and all over the floor.
To make matters worse, the car did not belong to my date. It was just a loaner. I spent the night helping her clean the car out.
89. Funeral Jams
I had a Hitch-style moment once. I met a girl at a party. We both loved music, and she mentioned her favorite band was also my favorite band at the time (Brand New, if you are curious). We make plans for her to come to my apartment and then go to dinner. When she gets to my place, I strategically have some Brand New playing in the background.
She hears the song and immediately begins hysterically sobbing. I’m freaking out, and then she reveals what’s going on. It turns out her grandpa had passed of cancer three months prior and the song (Guernica) was something she listened to multiple times a day to cope with his passing. Well, there was no coming back from that. We didn’t make it to dinner.
90. When You Gotta Go, You Gotta Go. Hard.
20-year-old me went out to dinner to meet her family for the first time. Got dressed up in nice khakis and a sweater. In the middle I farted but ended up pooping my pants with liquid ooze. There was no hiding the smell, as well as the HUGE FREAKING STAIN ON MY PANTS. It was awkward for all those involved.
91. When Ghosting Is The Kinder Option
Immediately after the date, I spent 20 minutes complaining via WhatsApp about how bad the date was. I thought I was talking to my friend with the same name as my date. It was my date and not my friend. I felt bad about it for weeks.
92. One Wild Ride
After a date, I dropped the girl off in the parking lot where her car was parked. We said goodbye to each other and parted ways without a kiss, as it was our first date. As she got out and began walking across the parking lot, I suddenly got the courage to whip my car around, stop it right in front of her, get out, and kiss her.
In my head, it was going to be like something out of a movie. In real life, it was a complete disaster. I pulled up to her, forgot to put the car in park, got out, walked away from the car, watched her look at me in horror and point, turned around, and ran towards my car as it slammed into another parked car. Just a typical day in my life really…
93. To Serve And Defect
He was in the Canadian forces. I asked him if he ever did any volunteer work overseas with his organization and he immediately spat out, “NO! I joined up to kill people, not help people.” I chugged my drink and got out of there as fast as I could.
94. Better Luck Next Time
I went out to eat with my date and proceeded to spill food all over myself. We went to go see a movie next and I fell asleep during it. When I took her home, it was still bright outside. Le fail. It was my first date, too.
95. Playing The Wrong Tune
Brought my date to my friend’s house. Friend pressures me into playing guitar. I played “Needle and the Damage Done”; first thing that came to mind. Why? Dunno. Turns out her brother had passed of a drug overdose not long before. Yeah, that date became very awkward and chilly after my little serenade…
96. Thank You, Next
Within the first five minutes of my date, this guy told me he killed his dog by leaving it in a hot car for 12 hours. When he realized I was horrified, he tried to pass it off as a joke. I left immediately.
97. Learning About Her Diary
Let me sum it up for you: I was already trying to escape by the time she told me about her poop diary.
98. Ice Cold
He took me to a minor-league hockey game and brought his brother. I went to the bathroom. The game ended and he left me there. He had to come back for me.
99. Sowing The Seeds Of Discord
Mid-date, he placed his hand on my stomach and said, “My son will grow here.”
100. He’s Not All That
When I was 15, I went abroad to Germany to study for a year. I was an awkward, anxious, nerdy girl and didn’t make any friends, though one charitable soul offered to set me up on a date with a guy she knew from another school. I’ve never been the dating type, but I went along with it in hopes that it might crack some of the boredom, and what the heck, maybe this guy and I might hit it off.
Fast forward to date day, and I ask the guy what he wants to do. It’s a small suburban town just far enough outside the nearest city for it to be a pain to commute to, and not big enough on its own to offer much in the way of entertainment for two teens on a blind date. This guy, Kalle, suggests going for a walk. Fine, I’m down with that.
So we walk around, grab a coffee, and talk for about an hour or so. That’s all the time I need to settle any doubt that this guy is not for me. He’s not a bad guy, he just lacks even the faintest glimmer of intelligence. I ask him about his hobbies, and he tells me that he’s interested in pipefitting because that’s the vocation he intends to go into at his father’s request, despite his own indifference.
I ask him if he likes to travel and he says no, but he’s traveled a bit in his life. Where did he travel? About 45 km west of the town he grew up in, when he got lost and accidentally crossed the border into the Netherlands on his moped. He then launches into a tangent, completely out of nowhere, about how women can’t and shouldn’t be allowed to operate motor vehicles. (Hypocrisy much???)
At school the following week, the girl who set me up with this guy asked how everything went. I tried to be as diplomatic as possible and said that he seemed like a nice guy, but we didn’t have much in common, and thanks for making the effort, but I’m not interested in a second date. This is when I found out the awful reality of the situation.
My host sister, who’d tormented me in subtle ways from pretty much within a week of my arrival, then joined my classmate and they both collapsed in paroxysms of laughter and high-fives. Apparently, the two of them had arranged this date as a prank, and had a bet with each other about if I would go on a second date with this guy.
And if I had slept with the dude, well…I don’t know. It never would have come to that. Needless to say that, upon learning of this scheme at my expense, I unleashed some serious fury.
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.
102. Flowing With Emotion
A woman was eight months pregnant. A guy brings her in for Valentine’s Day and has the mariachi band sing their love song. He pulls out the expected ring and she says yes. Things looked perfect! Only spicy Mexican food is perhaps not the best choice when your eight months pregnant. She hurriedly shuffled to the restroom five times. The fifth, she…didn’t quite make it.
It’s a tiny community, so I met them years later at a wedding party. I walked up and introduced myself. I mentioned I had met them years ago. “I was there years ago when y’all got engaged. The emotions were just… flowing that night?” The husband laughed until he cried, the poor wife just covered her face in shame.
Her: Man, this is a great steak!
Him: Did you say this is a great date?