There are some dates that are so disastrous, they’re unforgettable. When it comes to the dating game, these people struck out big time—but at least they were left with great stories to tell.
1. A Crash Course In Romance
We decided to meet in person at a local diner after talking online. I got there early, but everything went sideways the second she arrived. She hit the gas instead of the brake, drove up onto the sidewalk, and then slammed into a street lamp. The lamp came down and landed on a van parked nearby.
Somehow, no one got hurt, but she was obviously embarrassed. I haven’t heard from her since.
2. Fine Dining
I matched with a guy on Tinder who suggested we go out for dinner. I figured, “Why not?” so later that evening, he picked me up. Once we were driving, he asked where I wanted to eat. I answered casually, “Anywhere is fine.” I had no idea that would lead to such a disaster.
He smiled and said, “Alright then,” and pulled straight into a Subway parking lot. Then he told me he actually wasn’t hungry, but said I should get something to eat. So I awkwardly ordered food while he just stood there watching me. At that point I was already uncomfortable, but part of me kept wondering, “Could this get any worse?” It could.
A little later, I was back in the car holding a Subway sandwich I didn’t even want, while this genius drove us out toward a dark, isolated ravine nearby. We went about 10 minutes in before he stopped near an abandoned tennis court and said, “Okay, you can eat now.”
By then I was terrified, thinking, “I really hope this isn’t my last meal,” as I forced myself to eat that soggy sandwich while he watched. As soon as I finished, we drove back. I was so relieved to get home safely, and it took me days to fully process how awful that whole experience really was.
But that’s not even the end of it. The final twist was him showing up again at 2 a.m. with a bag of stale donuts and casually asking if I wanted to sleep with him.
3. No Means No
After a dinner-and-a-movie date, he asked if I wanted to “have some fun” and immediately took his pants off. I said no. He apologized for crossing a line, and I said, “It’s okay, I understand.”
Here’s the strange part: he somehow took my saying “it’s okay” as me changing my mind. So he started taking his clothes off again. It got very awkward when I had to explain that no still meant no.
4. Just Can’t Catch A Break
Back in college, I asked a girl to go to dinner with me and she said yes. I was excited, but I also felt pressure to pick a place that reflected who I was and what mattered to me. I wanted the choice to feel thoughtful.
There are two kinds of gifts: expensive ones and thoughtful ones. Since I couldn’t afford expensive, I decided to go all in on thoughtful. She was a freshman from Pennsylvania, and since we were in the South, I wanted to take her somewhere that felt new and uniquely regional. That’s when I landed on Bojangles.
Bojangles was cheap, the food was decent enough at the time, and it felt very Southern. I thought it would give us a chance to talk about food, culture, and the differences between the South and the North. The downside, of course, was that it was still low-end fast food.
The night of the date came, and I drove us there while talking about Southern life, comparing it to the North, and chatting about fried chicken and sweet tea. We got there, ordered, and waited for our food. Then we kept waiting, trying to make small talk through the awkwardness.
Eventually, my fried chicken and drinks were ready, but her sandwich was nowhere to be seen. We stood there awkwardly until an employee finally asked if we needed help. I explained we were still waiting on her sandwich, and that’s when we found out it had been sitting there ready the whole time. Not a great start—and somehow it got worse.
I picked up the tray and headed to a table, but ran into a problem. Bojangles was known for its sweet tea, and I had ordered a large one. The cup was shaped to fit in a car cup holder, which made it ridiculously unstable on the tray.
It tipped over and knocked her drink—served in a flimsy wax-paper cup—right off the tray and onto the floor. When it hit the ground, it burst open and splashed soda all over her shoes.
Trying to recover, I went and got her another drink. Then I sat down and realized I’d ordered fried chicken, which meant eating with my hands. Not exactly the best first-date choice. Wanting to avoid looking ridiculous, I tried using the little plastic spork Bojangles gave me.
That did not work. The spork couldn’t get the chicken off the bone, and while I was struggling with it, the piece of chicken flew across the table. Somehow, I managed to catch it midair.
At that point, I gave up and started eating with my hands. Assuming there would definitely not be a second date, I stopped trying to impress her and focused on getting through the meal with some dignity. But even that failed. Somehow, instead of getting the chicken into my mouth, I ended up wiping grease all over my face.
She looked at me like she was waiting for me to reveal it was all some kind of joke. We finished eating in silence. Ready to put the whole disaster behind us, I cleaned up the table and somehow threw away not just the trash, but the tray too.
We looked at each other, rushed back to the car, and left. I’ve had other bad dates, but this one really stands out. Honestly, I was surprised my car even started with how the night had gone. It was definitely unforgettable.
5. A Brutally Honest Red Flag
From my time working in bars and restaurants, I’ve seen some truly memorable moments. This one still stands out.
One fairly quiet evening, we had a dinner reservation for two at 6 p.m. A young guy showed up about 10 minutes early. He was clearly nervous and admitted it was a first date, which wasn’t something he had much experience with. It was honestly pretty sweet.
After we got him settled, his date showed up about half an hour late. She then drank far too much. Things got worse when she answered her phone in the middle of dinner and openly talked about her date to the person on the other end. From what she said, it was obvious she wasn’t interested in him—she admitted she had only agreed to come because she had nothing better to do.
Seeing how uncomfortable and disappointed he was, the young guy paid the bill and left. Thankfully, it didn’t seem to ruin his confidence. He’s a good guy, and I’ve seen him a few times at the bar where I work now.
6. TMI
My most awkward date was actually my very first online date. We’d been chatting on a dating app and decided to meet in person at a nearby cafe. I got there about 15 minutes early. When I arrived, she called to say she was running a little late.
I told her it was fine. A little while later, she called again—this time because she’d somehow locked herself out of her apartment.
So I kept waiting. About an hour after we were supposed to meet, a woman who looked like her profile picture walked into the cafe. Just as I was about to get up and say hello, my phone started ringing.
I answered, and she was shouting, “Where are you? Are you messing with me?” I told her I was sitting quietly at a table in the back of the cafe.
That first online date was definitely eye-opening, because I suddenly understood why some people only post photos of their face. She was much heavier than her pictures suggested. On top of that, she showed up wearing sweats. But even that was nothing compared to what came next.
After a little small talk, I casually asked how her day had been. She asked if I really wanted to know. Unfortunately, I said yes.
She immediately launched into a long rant about how she’d lost her last job because her coworkers had plotted against her. Then she said she’d started a new job, but it turned out to be fake and they stole her credit card information.
After that, she told me she’d just gotten out of an abusive relationship, and that her 25-year-old sister was abandoning the family to move to New York City. Then, as if that wasn’t enough, she said she’d been kicked out of school because people falsely accused her of planning to hurt someone. According to her, people were always unfairly accusing her of things.
I was stunned and couldn’t bring myself to leave right away. So I sat there for another painfully long hour, doing my best to keep the incredibly uncomfortable conversation going.
7. Are You Afraid Of The Dark?
Before I got engaged, I used to enjoy casual dating. There was one guy from high school I started talking to again. He was good-looking, and I thought going on a date with him might be fun. I suggested he come over to my place for a relaxed Netflix night instead of doing a formal dinner date.
He showed up, and everything seemed normal at first. We sat down in my living room to start watching Netflix. We were both on the couch, and the room was lit by one corner lamp. Out of nowhere, he said we should turn off the lights. I’m not a fan of complete darkness, so I told him the lamp gave us enough light.
Without saying anything, he stood up, walked over to the corner, and started slowly turning the lamp on and off. The corner he was standing in was right by the kitchen doorway, and he just kept flicking the light switch in silence.
I finally said, “This is getting weird, haha, please sit down.” While still flipping the light on and off, he replied, “Why... are... you... scared... of... the... dark?” Then he half-hid himself behind the kitchen doorway while keeping his hand on the switch.
Then he started doing this creepy little giggle like a child while still playing with the light. Needless to say, we did not go on another date after that.
8. Dine And Dash
We were both pretty low on money, so we decided to keep things simple and just go for a walk in a cute small town nearby. After that, we got McDonald’s and ate in the car so we could keep talking a little longer. Not long after, he started trying to pressure me into sleeping with him, saying I owed him because he’d bought me a cheeseburger.
It got even more unsettling after that. As he kept getting pushier, I told him we should stop at the gas station across town to pick up protection, but I had another plan in mind. Since I was driving, I took us there and asked him to run inside and get what we needed while I stayed in the car.
The second he went in and got far enough from the door, I drove off and left him there. This was back before cell phones were common, and the town didn’t have buses or rideshares, and most places closed by 6 p.m.
Later, through mutual friends, I found out he somehow made it home. But they all knew why I’d left him at the gas station, so nobody was especially sympathetic when he complained.
9. Doggone It
I met a guy at a business networking event. He seemed interesting. After we talked for a while, he invited me over to his place for Chinese takeout and a movie, but first wanted me to meet his four dogs. That sounded perfectly reasonable to me, because I absolutely love dogs.
I drove to the address he gave me, only to realize it was a trailer with a tiny fenced yard. I naturally assumed the dogs would be small. Instead, I was greeted by four enormous dogs with absolutely no manners, all packed into the trailer, which smelled strongly of dog.
To my surprise, “dinner and a movie” turned into digging through his huge collection of VHS tapes and DVDs while trying to dodge his advances, all in the middle of the chaos created by his giant dogs. I politely turned down his bold suggestion that we continue the night in the bedroom and left as quickly as I could.
The clothes I was wearing went straight into the wash when I got home, and sadly, my car smelled like dog for days afterward.
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10. Didn’t See That One Coming
When I was around 19, I was sitting at a bus stop killing time before work. A really beautiful woman sat down next to me. Before long, we started talking. The conversation felt easy, and eventually I worked up the nerve to ask if she wanted to meet up at a local coffee shop sometime.
To my surprise, she said yes. We picked a time and place to meet. As I got on my bus, she smiled and said, “It’s a date.” I showed up at the coffee shop at the agreed time and saw that she had already arrived. But she wasn’t alone—she had a guy with her.
At first, I didn’t think much of it. I figured he might just be there in case I turned out to be strange. So I sat down across from her and got a drink. Then almost immediately, she said, “So, what do you think about Jesus?” and opened a pamphlet she had brought with her.
Completely caught off guard, I said, “I thought we were on a date,” and she responded with something like, “I wasn’t sure you’d come if I called it that.”
I was so upset that I rushed out before she could notice I was about to cry. Looking back, that was definitely the worst date I’ve ever been on.
11. The Secret Ingredient
I once went on a blind date with a woman who kept picking at her scabs. She made a little pile of them right there on the restaurant table. At one point, I excused myself to use the restroom. When I came back, my soup had arrived, but the pile of scabs had somehow disappeared. Needless to say, I decided not to eat the soup.
12. What’s My Name?
I once went on a date with a coworker I didn’t know very well. Unfortunately, it was a complete disaster—he showed up drunk and treated everyone around us badly. The worst moment of the night came when he started heckling a small band playing at the bar.
Finally, the lead singer got annoyed and offered him $10 if he could guess my name. As you can probably imagine, he couldn’t remember it, even though we’d been spending the evening together, and this happened in front of a whole room full of people. The most unbelievable part came the next day, when he texted me and said, “You can have another chance,” as if I had been the one who ruined the date.
13. The Babysitter
I had been talking with this guy for a while, and eventually we agreed to go out. He said we’d do dinner and drinks, and he even offered to pick me up after work, which I agreed to. Then he texted me, “WE’RE on our way,” and I immediately replied, “Who’s we?”
It turned out he was a single dad. His sister had been supposed to watch his four-year-old son, but something changed at the last minute. I was surprised, but I decided to just go with it. He said he needed to stop at home first to shower because he was still wearing his work clothes.
When we got to his place, he got in the shower and somehow ended up falling asleep for about four hours. During that time, I hung out with his kid, who somehow managed to smack me in the face twice. After I told him not to do it again, though, we actually got along and had a pretty good time.
Honestly, the kid turned out to be great. Eventually the guy woke up from his nap, and we ended up just eating pizza. I took an Uber home afterward. I probably would have left much earlier if he’d been awake, but I wasn’t about to leave his child there alone.
14. Get My Good Side
I met a guy online. I lived in a medium-sized city, and he was in a very small town about 40 minutes away. He suggested I drive out to visit him. To be honest, I wasn’t thrilled about the idea. There wasn’t much to do in his town, and the place was extremely traditional, which didn’t feel ideal since we were both men. Still, I figured I’d give it a chance.
Most of the date was spent listening to him go on and on about some very strange conspiracy theories. He claimed that famous politicians and celebrities were part of a devil-worshipping Illuminati controlled by the Catholic Church. That sort of thing. But the weirdest part of the date wasn’t even what he said—it was how he physically positioned himself the entire time.
He stayed turned at about a 45-degree angle away from me the whole date. He sat crooked in his chair while we ate, and even when he stood up, he kept himself angled off to the side. At one point, I moved so I’d be directly in front of him and we could actually make eye contact. And somehow, he just turned another 45 degrees.
15. Let’s Never Speak Of This Again
I still cringe when I think about this date, and it happened about 12 years ago. We had gone out for food and drinks, and everything was going really well—we got along great. But as we started walking back to the train station, I felt a sharp pain in my stomach. I must have eaten something that didn’t agree with me.
I tried to stay calm and told myself I’d just use the restroom at the station. But when we got there, the restrooms were closed for repairs. The cramps kept getting worse, and I started sweating. I did my best to keep talking with my date, but all I could think about was not having a very public disaster.
When the train arrived, we got on. I couldn’t bring myself to use the tiny train restroom in that condition, so I decided to end the date early and told my date I needed to get home. My stop came up pretty quickly, so I gave a rushed goodbye and got off.
By then, the cramping, sweating, and discomfort had become unbearable. The second I stepped onto the platform, I started jogging toward the exit. But I tripped over my own feet and fell hard onto the station platform. The impact made me completely lose control of my bowels.
To make it even worse, my date saw the whole thing through the train window as it pulled away. We never spoke again, and we didn’t need to. We both knew exactly how that night had ended.
16. It All Came Crashing Down
This is a story about a close friend of mine. Her date took her to his regular rock-climbing gym in town. She told him she’d climbed before and seemed to be in pretty good shape.
But less than 30 minutes after they got there, the worst happened—she fell and broke her arm.
17. Licky Licky
I once went out with a guy I originally met at a coffee shop. He seemed nice enough at first, and we met for coffee again before deciding to have dinner at a bar. While we were there, something really strange happened.
I turned to get the bartender’s attention, and this guy suddenly—seriously—licked my face from my chin all the way to my temple. I was completely stunned.
Then he tried to act playful by poking me, but when I told him to stop, his response was way out of line. He leaned in and whispered, “I’ll just poke you while you’re asleep instead”...
I told him to leave immediately. A bouncer walked with me as I took him to his car, and stayed by the door to make sure I was safe.
A few days later, he sent me a bunch of messages. He said he was worried because he hadn’t heard from me and talked about “going to my parents’ house to make sure I was okay.” The scary part was that I had never mentioned my parents or where they lived. I warned him that if I ever heard from him or saw him again, I’d call the police.
Thankfully, I never heard from him after that.
18. Signs From Above
We went for a nice walk, and joking around, we started rolling down a grassy hill. Somehow we ended up behind a Mormon church and got a little too carried away. Then a Mormon man spotted us, scolded us for what we were doing, and stood there while we awkwardly got dressed in silence.
So we went somewhere else, both of us still complaining about how abruptly things had been interrupted. But the new spot turned out to be even worse—about 30 mosquitos decided my backside was dinner, plus I got two extra bites in some especially unfortunate places.
It was a whole mess. She didn’t get off easy either—she rolled over onto dog poop and started crying over what it did to her clothes.
It honestly felt like God was looking down and saying, “You two should just get a room.”
19. Money Matters
He took me to an Italian restaurant. Right after we ordered, he got a phone call. He started chatting casually, and then I heard him say, “Mom, I know, I picked the cheapest thing on the menu. Mom! I’m out with my girlfriend. I’ll tell you how much the bill is later.”
That bothered me for two reasons. First, it was our first date, and I definitely was not his girlfriend. Second, he lived with his mom—which, fine, I could maybe overlook—but what really threw me was how involved she was in his money. The fact that she called during our date to check what he was spending felt incredibly weird.
I went out with him one more time just to confirm whether he was really as odd as I thought, and he was. So I ended it there.
20. Running Him Ragged
Well, I ruined that first date. I badly misjudged how long it would take him (I’m a woman, and he was a man) to finish a seven-mile hike. In the end, I had to call a friend and ask them to contact the park rangers because we were still out on the trail after 9 p.m.—well after the park gates had closed.
During the last stretch—the brutal final three miles—he really started giving me the ick. He was cheering on his own legs and joking about eating the frogs hopping across the trail. It was completely dark, and he had left his phone behind, so I used mine as a flashlight the whole way back. I’m sorry, dude. You were actually really nice, and I truly didn’t mean to wear you out so badly on that hike.
21. Drink Up
I connected with a girl online, and we started talking. Things were going really well—we were texting all the time and seemed to click. Eventually, we decided to meet for dinner, and while everything seemed okay at first, she did come across as a little unusual.
During dinner, we ordered a round of margaritas. After just the first one, she suddenly stopped talking in the middle of a sentence and just stared at her hands. I asked if she was okay, and she said, “Oh, sorry, I’m a little tipsy.” I was surprised and thought, “Really? We’ve barely started drinking.”
Then she admitted, “Oh, I’ve actually been drinking all day.” That made me think back to our earlier texts, when she would often message me saying things like, “Hey, I’m a little tipsy on my way home, keep me company.” At that point, I started wondering if this was a regular thing for her.
Then, out of nowhere, she passed out and hit her face on the table. At first, I thought she was kidding because it seemed so dramatic.
I started to panic when she didn’t move, even after I laughed. I had to wake her up and quickly asked for the bill, which was a lot higher than I expected.
She then asked if I could walk her home, and even though she was clearly not doing well, I agreed. After we’d been walking a while, I asked how much farther it was, and she told me it was still another mile.
Eventually, we made it to her apartment. She offered me a drink and asked if I wanted to stay over, but I politely said no. She got offended and immediately told me to leave. And that was that. I ended up using GPS to find my way back to my car.
22. Drama King
Technically, this one is more about ending things than a bad date, but it happened during a date. I tried to break up with him privately while we were sitting in the car. He asked if we could pause the conversation for a minute, then walked us into a restaurant and, to my surprise, started crying in the middle of the place.
The strangest part? A few weeks later, he showed up at my job acting like we were still together. So I had to break up with him... again... while he cried... and his sister, who also worked with me, was there too.
23. Telling Tall Tales
One time, I had to play rescuer during a friend’s date. The moment she suddenly got up to go to the bathroom in the middle of it, I knew I was about to get “the call.” She came back and kept talking for a bit, and honestly, the excuse she used was pretty creative.
She didn’t go with the usual “my friend needs me” line. Instead, she made up a whole story about a bus crash and said she had to rush back to the hospital to help several badly injured children. It was definitely one of the more memorable excuses I’ve heard.
24. Good Enough
My first date—and still the worst one I’ve ever been on—started with an unbearably long car ride. The whole time, he talked nonstop about how much he loved club life and the benefits of bottle service. We finally got to what he described as “a low-key enough restaurant for a girl like you.”
As soon as we ordered, he nervously checked his bank balance. Then he bluntly told me I needed to pay for dinner—which I honestly would have been fine with if he’d asked a little more politely.
For the rest of the meal, he acted like he was the only one allowed to talk. He launched into a strange rant about how he believed the Earth was flat and how he planned to become a senator of Mars within ten years... and somehow it kept getting worse.
He made it very clear that any woman who wanted to date him seriously would need to fully support his goals. After dinner, I ended up following him into a club since he was my ride.
When he happily said, “This is going so well,” I had to tell him that it really wasn’t, especially since I’d barely gotten a chance to speak. When he asked for examples, I told him directly that it was the worst date I’d ever had. Completely unfazed, he sat down next to me and said, “So maybe we can start as friends and see where it goes?”
My answer was to call an Uber. He kept texting me every day for another date for a week, and eventually I blocked his number.
25. Shortchanged By The Universe
I got to the coffee shop way too early because I was really nervous. As I parked, I realized I’d left my wallet at home. Of course, the coffee shop was half an hour away, and we were supposed to meet in ten minutes.
I dug around in my car for change and managed to come up with $2 in quarters, nickels, and dimes. I rushed inside and bought the cheapest coffee on the menu. She walked in and looked surprised that I’d already ordered. Not exactly a great first impression—not offering to buy her coffee because I only had a handful of coins left.
We sat outside, where the setting sun was shining directly into my eyes. I was too stubborn to suggest moving, so I spent the next hour squinting in full sunlight. The conversation was actually pretty good, but everything fell apart when I shifted in my wooden chair and heard a loud crack.
Sure enough, the chair had broken. I know I’m a bigger guy, but did that really have to happen right then? So I can’t say I was shocked when she never called me back after that first date.
26. Well, That One Backfired
I haven’t been on many dates, but the worst—and funniest—one happened because of Tinder. The plan was to start the night as a double date at my place, and then, if things went well, we’d split off and spend the rest of the evening alone.
But we never got that far, because he clogged my toilet with way too much toilet paper. He was absolutely horrified when my friend found out, and he left almost immediately. To make it even funnier, he was in such a rush that he forgot his coat, so one of his friends had to come by the next day to pick it up.
27. Dr. Yuck
During our conversation, he told me, “I’m not trying to brag about my job, but just so you know, I save lives every day.” What he meant was that he was a doctor. And no, he wasn’t being sarcastic at all. Then things somehow got worse. He started getting annoyed because he had messaged me on a dating app five years before our date, and he was still upset that I hadn’t replied right away.
When I explained that it was an old account I hadn’t used in a long time, he gave me this smug look and said, “That just shows how fickle girls are…” And then came the final surprise: he admitted he had strep throat and said, “I really shouldn’t be on a date right now.” So gross.
28. Third Time’s The Charm
When I was in tenth grade, I made plans to go see a movie with a date. At the first theater, they asked us for ID, which had never happened to me before.
I completely panicked. Since I was under 18, I couldn’t buy the tickets. At the second theater, the air conditioning had broken, and it was around 95 degrees inside, so the movie was canceled.
At the third theater, we ran into another problem—there weren’t two seats together. Even so, my date still wanted to see the movie, so we ended up sitting in separate rows. As you can imagine, there was no second date.
29. A String Of Bad Luck
Honestly, it’s hard to choose just one worst date. I’ve had plenty of dating disasters. One person seemed totally normal at first, until she turned the whole conversation toward the idea that we’re all living in some giant simulation, like The Matrix.
I also dated someone who had a serious biting problem. Showing up to work and family events with a bruised-up neck was not fun, and honestly, it made me feel unsafe. Another time, a date abandoned me at a club, leaving me stuck in a huge crowd, which was way outside my introvert comfort zone.
And to round out the disaster collection, I remember one night when I had to walk home alone and ended up having an embarrassing accident because I was way too drunk and going through a rough patch emotionally. So yeah, dating has definitely been a rocky experience for me.
30. Is That My Ride?
A friend of a few friends asked me out once. He got my number and called to set up a dinner date. At one point, he asked if I’d be okay with him picking me up in the vehicle he used for work.
I’d worked in business settings for a while, so I assumed he meant some kind of company car. No big deal, right? Looking back, I probably should have asked what he actually did for work.
Then the night of the date arrived, and he pulled up... in a garbage truck. But somehow it got even worse. I thought, “Well, I did say yes,” so I got in, and we went to dinner.
I’m guessing he was really nervous, because he drank way too much. He got so drunk that he actually asked me to drive his giant garbage truck back.
The problem was, this thing had four gear shifts, and I only know how to drive automatic cars. Somehow, this ridiculous guy still ended up driving me home—in the garbage truck. Then he actually asked if he could spend the night.
There definitely wasn’t a second date.
31. Playing With Fire
My first dating experience easily wins as the absolute worst. The girl I was with started lighting matches, putting them out with her fingertips, and then chewing on the burnt end of the matchstick.
32. Just Watch Me
My most disastrous date happened back at boarding school on a college campus. We were both rule-following nerds, so we decided to go to a party at the student center. But after about 15 minutes, he got bored, and we slipped away into the campus buildings. I thought we were sneaking off for a little romance? Nope.
Instead, he completely ruined his chances with me. We found a computer lab, and he spent the next two hours showing me how he played League of Legends while trying to explain the entire game. So if you meet a handsome, single guy, there may be a reason.
33. It Was Like Watching A Car Crash
Her profile picture online was cute, and we had four or five pretty normal conversations before deciding to see a movie for our date. I’m usually not a fan of movie dates since they don’t leave much room for real conversation or getting to know each other, but I thought, “She seems nice, what could go wrong?”
Keep in mind, she was the one who chose the movie time and when I’d pick her up, so it’s not like she didn’t know there would be a bathroom nearby. The theater was only about 15 minutes from her place.
The second she got into my car, it was obvious she was intoxicated. She even jokingly threatened to kick me if I tried anything stupid. All of that happened in less than 10 minutes.
Right at the 10-minute mark, she asked me to pull over, and what happened next completely shocked me. She got out of my car on a fairly busy highway and, right in front of me, started peeing.
It was one of those moments that’s hard to process. Once my brain caught up with what was happening, I leaned over, closed the passenger door, and drove away.
34. The Double Date Disaster
So here’s a picture of my very first date. I had just turned 16, and the guy from school was fairly cute. My expectations weren’t high, but somehow, he still managed to fall below them.
I’m not big on trusting people, so I insisted we go out with another couple. He had lots of friends I knew, so he promised it would be fine. But when I got to his house, the “other couple” turned out to be his aunt, who lived with him.
So picture this: a 21-year-old aunt, a clueless 16-year-old me, and a guy who had no idea he was supposedly on a date because he thought we were all just hanging out.
To make things even stranger, the aunt decided to cook Hawaiian haystacks for her Polynesian date, who had no idea what they were. He walked into badly burned rice, managed to save it, and the rest of the meal came straight from cans.
As if that wasn’t enough, they decided it would be fun to throw blades around in the backyard. After I did better than my date, and his aunt accidentally hit him with an airsoft BB, he got really upset.
Trying to improve the mood, his aunt suggested we go bowling. I was wearing ballet flats, which meant I had to borrow his giant nerdy socks from around 2010, complete with stains I didn’t want to think about.
Before we left for bowling, he tried to repair his bruised ego by kicking a spider on the wall, but instead he kicked a hole in the wall and got his leg stuck. His aunt had to help him out. I was not impressed.
Eventually, we made it to the bowling alley. Things started out okay, but got awkward fast when we learned the manager was the aunt’s recent ex. To top it all off, he tried to kiss me in the back seat of the car while his aunt and her date watched. She actually cheered.
You’d think that was the end of us, but somehow, that wasn’t even the worst date I went on in high school.
35. Taste Test
He dipped his fingers into my dessert, tasted it, and then did it again. I had ordered lemon meringue pie and politely asked if he wanted a bite. At first he said no, but then changed his mind and said, “Actually, it does look good.” Then he stuck his finger in it and licked it off. So gross.
36. A Night To Remember
A few years ago, I took a long trip during a really difficult time in my life. I went to Colombia to learn Spanish. One night, while I was out with some friends from my language school, I noticed an incredibly beautiful woman. Even though my Spanish was still pretty basic, I felt determined to ask her out.
So I did—I worked up the nerve and asked. To my surprise, she said yes. The next day, when our date came around, I wasn’t feeling great, but I was too excited to let that stop me. As planned, I picked her up and we went to a nice restaurant. After dinner, we took a walk along the beach—a little cliché, but true.
That’s when I started feeling much worse. I got dizzy, and then the unavoidable happened. I got sick—and not just a little. It was dramatic enough that everything after that is kind of a blur. Eventually, I woke up in a hospital.
To my amazement, my date was sitting there beside me, now wearing workout clothes because the whole incident had unfortunately made a mess. She was genuinely worried and said she was sorry we hadn’t gotten to finish our date. Years later, we’re now getting ready to get married.
37. He Got Gassed
The craziest date I ever had started out like a pretty normal high school scenario. A girl invited me over while her parents were out of town for the weekend. I was into the idea, and everything seemed to be going well.
Later that night, we ended up lying in bed together. Out of nowhere, she fell completely asleep—snoring away—while I was still wide awake at 3 a.m. Then she shifted a little and suddenly let out the loudest gas I’d ever heard.
And it just kept going. At first, I thought it was her old dog. But no. Once the smell reached me, I almost gagged. I pulled my shirt over my face like a mask and could only wonder what she’d eaten.
And somehow, the final touch was the little satisfied sound she made when it was over. That was too much for me. I couldn’t stay. I quietly got dressed, tried not to wake her, and slipped downstairs and out the front door. Luckily, she lived close by, so the walk home wasn’t too bad.
Of course, she asked me the next day why I had suddenly left. But I just couldn’t bring myself to tell her. It felt like it would have been way too embarrassing for her.
38. Three’s Company
I was planning to take a girl to the movies when she asked, “Can my best friend come too?” There went the romantic vibe, but trying to be nice, I said, “Sure!”
Then she showed up with her friend, who turned out to be a guy. That’s when I learned this “best friend” was actually her ex, but they were still really close and supposedly just friends now. At that point I figured the date was already off track, so I might as well try to make the best of it. I paid for our tickets, even though she offered to pay for her own.
Right after that, she turned around and bought her ex’s ticket. Strangely, we all got along well enough, and the mood wasn’t bad, but the whole night felt like a tug-of-war while I tried to get her attention. Unsurprisingly, I lost. They were best friends, after all.
When I got home, her guy friend added me on Facebook and messaged me, “Don’t try to make her your girlfriend—she’s bad at it.” I did get to take her to the movies alone one more time, but things kind of fell apart after that. I really liked her, but it was obvious I didn’t mean that much to her. I guess that’s how it goes.
My advice to anyone planning a date: skip the movies. They don’t always work out the way you hope.
39. Clownin’ Around
It wasn’t my worst date, but it was definitely the weirdest. I was out with a girl who seemed like my type: attractive, funny, and into a lot of the same things I liked. We were at a bar she liked, getting to know each other, and the usual first-date questions started coming up.
“So, you said you work in an office, but is that what you really want to do?” I asked. “Did you study for that?”
She answered, very seriously, “Actually… I’m in clown school right now,” and then pulled a bright red clown nose out of her bag and put it on.
If this had happened on our third date, it probably wouldn’t have been so surprising. But this was our first time hanging out one-on-one, only about a week after meeting, so I was caught completely off guard. Still, she was cute, and I was curious.
So I said, “Wow, that’s really interesting. I didn’t even know clown school was a real thing.”
“It is, and it’s very competitive.”
I said, “Really? Is it like a clown university, college, or trade school?”
Apparently, she took my joking question as an insult. Ironically, for someone in clown school, she didn’t seem to appreciate the humor.
40. Equality At Any Cost
I once went out with a guy who wasn’t really my type physically, but he seemed nice enough. The problem was, he spent our entire date bragging about how much money he made. We shared a pizza—I had one slice, while he ate about six. And that wasn’t the end of his bad manners.
When the bill came, he suggested we split it evenly “because that’s how people do it now.” Then, after he drove me home, he tried to kiss me—and honestly, his breath smelled unbelievably awful.
41. Got Milk?
A few years ago, I went on a coffee date with a guy who was studying nursing. He told me a very intense story about how he and his ex-girlfriend had helped an elderly woman use the bathroom at a party. He said it wasn’t even the first time he’d done something like that—his girlfriend just happened to be there to help.
It was a pretty uncomfortable story, and I quickly came up with an excuse to leave. The funny part came a few days later. He texted asking if I wanted to go out again. I didn’t reply. Then the next day he sent another message: “It was the bathroom story, wasn’t it?”
42. An Awkward Introduction
So there I was, sitting alone at the coffee shop. She called and said she had a sudden emergency and couldn’t make it. I’d only been waiting three or four minutes, so I didn’t mind much. I figured, “Why not see what a friend is up to?” so I gave him a call.
Long story short, he was across town at a bar. So I went to meet him. Turns out he had just met a really nice woman during a game of pool and introduced us. That’s how I ended up meeting my date for the evening.
43. An Icy Encounter
Back in university, a girl I really liked invited me to go ice skating with her and some friends. The problem was, I had no idea how to skate and couldn’t pick it up quickly.
Still, I really wanted to impress her somehow. That did not happen. Instead, I spent the whole time holding onto the sides of the rink and making a total fool of myself.
The low point came when I slipped and fell flat in front of a crowd right as someone took a photo. My most embarrassing moment ended up being perfectly captured forever.
After that disaster on the ice, she walked me back to my apartment, and whatever chance we had at a relationship pretty much ended there. But every cloud has a silver lining.
As it turns out, my now-wife was also at the rink that night. We didn’t realize it until a couple of years into our relationship, when she suddenly said, “You were that guy who couldn’t ice skate! Yeah, that girl did not seem very into you.”
44. Bragging Rights
On our second date, he proudly told me a few things about himself. First, that he had managed to collect unemployment benefits for a long time.
Second, that he could always talk his mom into letting him move back in, even after she had kicked him out. And third, that he had basically paid for a dancer’s $3,000 implants, even though he got nothing back from it.
But the worst part came next—he admitted he had spent about four months in jail for waving a weapon around while showing off to some teenagers, though he insisted he never planned to use it. He said it in more of a casual brag than a serious confession. It was surprising, because he had seemed so pleasant on our first date.
At that point, I was quietly entertained and trying to figure out how to end the evening. Luckily, I didn’t have to, because he already had plans to meet his friends at the video store after dinner.
45. Laying All Her Cards On The Table
The worst date I’ve ever been on? The woman I was with had Crohn’s disease. In the middle of dinner, she took out her medical urine bag and told me I should look at it so I’d understand what dating her might involve. Unfortunately, her catheter tube knocked over her drink. It was an awkward situation. I really felt for her.
46. Momma’s Boy
On our first date, he tried to impress me by taking me to dinner at his mom’s house. Also there: his brother and his mom’s very eccentric roommate. After dinner, we all ended up watching *Iron Chef*, and since there weren’t enough chairs, we sat on the floor. During the show, his mom somehow started talking about using vibrating appliances for household chores because it might make cleaning more entertaining.
Here’s the best part: he didn’t even live with his mom. Needless to say, that was both the start and the very quick end of our dating story.
47. The Ole Switcheroo
My worst date started out like a normal date and somehow ended as a multi-level marketing pitch. The one bright spot? I still have those Cutco scissors, and honestly, they’re pretty decent.
48. The Stench Of Success
This happened on my third date with a woman. We went to a Poison-Def Leppard concert. Since we hadn’t eaten before the show, I grabbed a chicken salad sandwich from a nearby gas station to settle my empty stomach.
Partway through the concert, I suddenly really needed the restroom. But the stalls were a complete mess. Since we had VIP tickets, I decided to wait and stop at the VIP bar on the way out.
Once I got in there, the smell from my visit caused a reaction from a few guys nearby, which I couldn’t help finding a little funny. After the concert, we pulled the car out from the front parking spot so we could sit and relax for a minute. Then the second wave hit, and this time it was much worse.
I was gripping the steering wheel, sweating, and feeling miserable. Then I had an idea: maybe letting out a little gas would ease the pressure. It did not.
My pants were ruined. I ran into the nearby woods to deal with the rest of the situation and used my undershirt as makeshift toilet paper.
In spite of that unforgettable beginning, we’ve now been happily married for 12 years and have three kids.
49. Showing Off His Creepy Side
One night, I blacked out a little at a nightclub and met a man in a suit named Willis. The next morning, I found a message from him on my phone. The funny part was that neither of us really remembered the other very clearly. Still, he seemed nice over text, so we thought it would be funny to go on a date.
At lunch, though, my first impression of him wasn’t great. He was socially awkward and came across a little intense. Still, he seemed harmless enough, so we got pizza and started talking.
At one point, I told him I was studying public policy. I was pleasantly surprised when he showed real interest in my area of focus, since most people usually don’t.
I explained that I care a lot about improving education policy because I truly believe education can change lives, especially for people growing up with fewer opportunities.
After listening to all that, he said, “That’s interesting, but I really don’t see why low-income people need education. When I’m older, I want maids and butlers in my house—someone has to do those jobs.”
I brushed past it with a polite, “Everyone’s entitled to their own opinion,” while quietly trying to figure out how to end the date. Unfortunately, it got even worse.
When we finished eating, I made up an excuse to leave about an hour earlier than planned. He looked disappointed and joked, “I should just kidnap you and keep you here.” I told him that wasn’t something to joke about. His response? “I’d hide your body right there, haha.”
I got a taxi immediately after that.
50. Just Pop A Squat
I was in France, having a lovely dinner at an outdoor cafe with a woman I’d met the day before. Then things took a very unexpected turn.
She excused herself to go to the bathroom, stood up, walked a few steps away, squatted, and peed right into the street gutter. Needless to say, there wasn’t a second date.
