There are some dates that are so disastrous, they’re unforgettable. When it comes to the dating game, these Redditors struck out big time—but at least they were left with great stories to tell.
1. A Crash Course In Romance
We met online and agreed to meet at a diner we both knew. I got there first. But the night took a horrifying turn the moment she arrived. Just after pulling in, she hit the gas instead of the brake, drove into the curb, then hit a light pole which fell over and landed on a parked van.
No one got hurt but she was pretty embarrassed. Never heard back from her.
2. Fine Dining
I matched with this guy on Tinder and he offered to take me out to dinner. I thought that sounded nice, so later that night he picked me up. We were driving and he asked me where I wanted to go. I told him I was fine with anything. BIG MISTAKE.
He said, "Okay then," and pulled into Subway. He then told me that he wasn't hungry, but that I should eat! So he stood outside of the Subway and watched while I went in and got myself food. At this point, I was already mentally done but I wanted to see how much worse it would get. Spoiler alert: it got so much worse.
So I'm sitting in the car with the stupid freaking sub on my lap, and he decided that it was a great idea to drive around, specifically through a dark, isolated ravine that was nearby. He drove for about 10 minutes into the ravine, parked the car next to an abandoned tennis court and said, "Okay, you can eat now”.
I was just thinking, "I really don't want to die here," so I choked down the soggy sub while he stared at me. The second I was done, he pulled the car out and drove me back home. I was so grateful to make it home in one piece that it took me several days to process how screwed up the entire date was.
But here’s the cherry on top: at 2 am that night, he came back to my house uninvited, carrying a bag full of stale donuts, and asked me if I wanted to sleep with him.
3. No Means No
After a first date of dinner and a movie, he asked if I’d like to “have some fun” and took off his pants. I said “No”. He apologized for overstepping himself and I told him, “Hey, I totally understand and it’s okay!”
Now here’s the confusing part...he took my word “okay” as consent for “I totally want to do it now”. So he immediately took off his pants again. It was so awkward when I explained it was still a no.
4. Just Can’t Catch A Break
Back in college, I met this girl and asked her if I could take her out to dinner. She said yes. I was ecstatic. Well, then I had to figure out where to take her to give her an idea of who I am and what I'm about. So I tried to do something that was thoughtful.
I've learned that there are two types of gifts: expensive and thoughtful. If you can't do expensive, which I couldn't, then you'd better go hard on the thoughtful. This was taking place in the southern US, but she was a freshman from Pennsylvania. I started thinking about things that be new and interesting to her. The answer came to me in a flash: Bojangles!
I would take her to Bojangles. It's cheap, it used to have fairly decent food, but most of all it's southern, and we'd be able to discuss regional differences in food and culture. Of course, it's also fast food. Really crappy fast food.
The evening of the date arrived. I drove her to the place and talked all about fried chicken and the South and tea and how it must be different from the North. We got there and ordered at the register, then moved down to pick up our tray of food. We waited. And waited.
I tried to make some small talk. You know, the small talk you make when something could interrupt your conversation at any moment...Then we waited some more. Finally, my dinner (fried chicken) was on the tray. The drinks were on the tray. Her sandwich was not.
So we stood there and stood there with the silence growing more and more awkward. Minutes rolled by that felt like ages. Finally, an employee noticed us standing there and said, "Did you need something?" I said yes, that we needed her sandwich.
The employee turned around and grabbed the sandwich from the place it had been sitting THE WHOLE TIME WE'D BEEN STANDING THERE and put it on the tray. It had been there since the beginning. Not a great start.
I picked up the tray and started walking back to a table with her. But there was an issue. Bojangles used to have the best sweet tea, so I always got a large. The cups they use for the larges are the kind that are smaller at the bottom, so they'll fit in your cup holder in your car.
That's great for a car, but NOT so great for balancing them on a tray. It fell over. Fortunately, it fell over onto the tray, but not before knocking her drink off of the tray onto the floor. She had gotten the smaller drink, which came in the waxed paper cup instead of the plastic cup that the larges are in.
That's important, because it means that when her cup hit the ground at about a 30-degree angle, the cup crushed and LAUNCHED the liquid inside out like a cannon. Onto her foot. Drenching her in Pepsi or Coke or some soft drink.
Being gentlemanly, I went and got her a new drink. I got back to the table and started trying to eat. I had ordered fried chicken, which I realized would mean that I had to eat with my fingers, which was stupid on a first date.
Not wanting to look dumb(er), I decided I'd try to avoid eating with my fingers by using the plastic cutlery provided by the store. This would have been a fine idea if not for the fact that Bojangles only provides you with a spork. Not a fork, not a spoon, not a knife. A plastic spork.
I'm trying to pry the chicken off the bone with this plastic spork and it's going nowhere. I can't get the chicken off the bone. I dug in a little deeper and really pulled, which bent the spork back a little, which served as a spring to launch my chicken across the table. I actually caught it before it could hit the floor.
I remember thinking to myself, "Well, just enjoy this chicken because this date is going NOWHERE”. I decided to just forget it and eat the dang chicken with my fingers. She was obviously not going to be going out with me anymore, so I decided not to worry about impressing her, just try to get out of the situation without looking any dumber than I already did.
I reached down and pulled off a nice piece of chicken with my fingers….and I missed my mouth. Seriously. I jammed the chicken onto my face. I don't know how I missed it, but I did. I just missed. Which of course smeared chicken grease all over my cheek. Oh, but it doesn't end there.
The girl was looking at me like she was waiting for me to tell her, "It's just a prank, bro!" I felt so dumb. We finished eating in silence. Finally, I said, "Well, let me take you back to your dorm”. I gathered up all the trash on the tray, walked over to the garbage can, and accidentally threw the whole thing into the trash. All of it, cups, the spork, napkins, THE TRAY. All of it.
I looked at the girl, she looked at me, and we both ran to the car. I've had some other bad dating experiences, but this one took the cake. I also remember being shocked when the car started when we were leaving. After the night I'd had, I was fully expecting to have to walk several miles back to campus in the dark.
5. A Brutally Honest Red Flag
Working in bars and restaurants, I've been able to witness some absolute doozies. And boy does this one take the cake.
So, it's a fairly quiet night and it's pretty early, and I have a reservation for 6 pm for two people. A young guy shows up for that reservation about 10 minutes early. He tells me he's very nervous, as he's on a first date, and hasn't been on many of them, all that kind of jazz. It was kinda sweet, really.
Anyways, I seat him, and the girl arrives, like, 30 minutes late. She then proceeds to get extremely inebriated. About halfway through the meal, though, she answers her phone, takes the call, and starts talking about her date in front of her date, saying stuff like, "He's not really my type, I don't exactly like him but I figured I had nothing else planned tonight so why not".
The young man looks super discouraged, pays his bill, and leaves. Luckily, he didn’t let that date discourage him. He's a nice lad, I've seen him a few times at the bar I work at now.
6. TMI
My worst date was my first-ever online date. We had been chatting on a dating website and agreed to meet at a cafe. I showed up about 15 minutes early. She calls me and says she is going to be a little late. I say “no big deal”. 25 minutes later, she calls me again and says she is going to be late as she locked herself out of her apartment.
I wait and wait. At this point, it's an hour after the agreed-upon time. I see a woman who matched her picture enter the cafe. Before I can go up to meet her, my phone rings. I picked it up, and she proceeds to shout at me, "Where the heck are you? Is this some sort of prank?" I tell her that I am at a table in the back of the cafe.
My first online date was informative, as I learned why some women only post pictures of their faces. She was extremely overweight. Furthermore, she was only in sweatpants and a sweatshirt. But all this is minor compared to what happens next.
After making some small talk, I ask her how her day was going. She asks if I really want to know. I mistakenly say yes. She launches into a rant about how she got fired from her last job because people were plotting against her, and a new job she signed up for was just a scam that stole her credit card information.
She also just got out of an abusive relationship, and her 25-year-old sister was abandoning the family to move to New York City. And on top of all that, she was just kicked out of school because people said she was plotting to kill someone, but she swears she wasn't. "People are always plotting to get me, it seems".
I was too frozen to leave at that moment and stayed for about another hour trying to make the most awkward small talk ever.
7. Are You Afraid Of The Dark?
Before I got engaged, I was casually dating. I started chatting with this guy from high school—he was good looking and I figured I’d give it a shot with him. We were supposed to go out on a date, but I didn’t feel like getting all dressed up so I suggested he come over to my place and we could Netflix/chill.
He comes over and everything is cool until we sit in the living room to watch Netflix. I sit on my couch, and he does too. I had a corner lamp on in the room. He said, “We should turn off all the lights”. I’m like eh, the corner light is fine! I personally didn’t want to be in the pitch-black dark.
But then he gets up, creeps over to the corner light, stands with his back completely against my wall, and begins to flicker the light slowly on and off…Next to the corner is the doorway into the kitchen. He is literally not saying a word, just flickering the light off and on.
So I say, “You’re creeping me out, lol, please sit”. And he says, in between flickers, “Why...are....you... afraid... of... the... dark”. He then shuffles behind the doorway so I can only see HALF of his face and body. He has his arm reach around the doorway so he can still control the light.
He then begins giggling like a little kid and continues to flick the light on and off. Needless to say, no more dates after that.
8. Dine And Dash
We were both broke, so we went walking around this cute, teeny tiny country town near us, and then got McDonald's to eat in the car so we could chat some more. He almost immediately starts pressuring me to go sleep with him because he bought me a cheeseburger, so I owe him, he says.
He starts getting pushy, and I say, okay, but let's go purchase some protection from this gas station that's on the other side of town. I drove for this date, so I take us to the gas station and tell him to go get the stuff while I wait. I knew exactly what I had to do.
I wait for him to get in the door and go a bit farther into the store before I drive off, leaving him stranded in this tiny gas station in the days before cell phones got popular, in a tiny country town with no bus service, no ride shares, and everything shuts down by 6 pm.
I know from mutual friends he made it home, but they already knew why he'd been ditched at the gas station, so no one cared about his whining about it.
9. Doggone It
Met a guy at a professional night out. He seemed interesting. He invited me out for Chinese food and a movie, but insisted I come by his house first to meet his four dogs, because not liking his dogs would be a deal-breaker. Cool, I love dogs.
I follow directions to his house, which is a mobile home with a small, fenced yard. So the dogs must be little, I think. NOPE. There were four large, mannerless dogs living inside this mobile home and the smell is completely encompassing.
Turns out "dinner and a movie" meant watching one of the thousands of VHS tapes and DVDs he owned while he tried to get the clothes off me, while four big dogs bounced around. I declined his kind offer of an incredible time in the bedroom and got out of there.
My clothes went directly into the washer and my car smelled like dog for days.
10. Showing Off His Creepy Side
I once browned out at a club and remember briefly meeting a guy in a suit. The next day, I woke up to a text from Willis, the guy in the suit. Turns out we both didn't really remember each other. Over text, he seemed nice enough and we both thought it'd be a funny experience if we went on a date.
We met up for lunch and upon meeting him, I didn't really have much hope for a second date. He was kind of awkward and tried a little too hard to stunt. But whatever, he seemed like a nice guy. We sat down for pizza and started getting to know each other.
I told him I was studying public policy and was delighted when he asked what kind of policy I wanted to focus on (most people don't really care). I went on a whole rant about how much I wanted to make education policy better because I thought education had the potential to dramatically change lives, especially for those not born into much.
After I finished my rant, he says, "That's cool but I don't really believe in education for low-income people because when I grow up, I want maids and butlers and, like, someone has to do that”. I responded, "Some people have that viewpoint," and started to look for ways to end the date. But the worst was yet to come.
After we finished eating, I made up an excuse to leave an hour earlier than planned. He asked if I really had to go and said, "I should just kill you and keep you with me”. Smooth. I told him he probably shouldn't joke about that. He responded, "I would bury your body right there haha”.
I hailed down a cab after that.
11. The Secret Ingredient
I went on a blind date with a lady who wouldn't stop picking at her scabs. She just made a pile out of them on the restaurant table. I excused myself to use the washroom and when I came back my soup was there, but the pile of scabs wasn't. No, I didn't eat the soup.
12. What’s My Name?
I went out with a guy from work who I didn't know much about. He turned out to be awful in many ways and was intoxicated when I showed up. The lowlight of the night was when he started heckling the small cover band that was playing in the bar.
The guy on the mic said, "I'll give you 10 dollars out of my own pocket if you can tell me this girl's name" and—you guessed it—he literally blanked on my name in front of a room full of people. But here’s the kicker: The next day he texted me saying, "You can try again,” as if I was the one who blew it.
13. The Babysitter
I'd been talking to this guy, and we finally decided to go on a date. He said he'd take me out for dinner and drinks. He offered to pick me up after work, so I said okay. He sent me a text saying "WE'RE" on the way. I immediately asked, “Who is we??”
Well, he's a single father, and his sister was supposed to be watching his four-year-old son, but something came up. Uh...Okay, I still went along with it. So he said he wanted to go home to shower first since he was in his work clothes.
We got to his house and he showered and fell asleep for like four hours while I hung out with his child who smacked me in the face TWICE. Luckily, after I told him not to do that anymore, we ended up getting along and having fun.
Turns out, he's a sweet kid. The guy finally woke up and we ordered pizza. I took an Uber home. I would have left before he woke up, but I didn't want to leave his kid alone.
14. Get My Good Side
I met someone online. I live in a mid-size city, and he lived in a small town about 40 minutes away. He asked if I would drive to him, which I wasn't wild about since there's not much to do in his little town and since we're both men and his town is very conservative, but I went with it.
He spent most of the date going on and on about conspiracy theories he believes in (all major politicians and celebrities are Illuminati satanists run by the Catholic church, etc). But the most unsettling part? He literally faced 45 degrees away from me the entire time, making sure I could only ever see him in profile.
Like, he sat sideways in his chair at dinner and always turned to the side while he was standing. At one point I stepped around into his field of view so we could look at each other, and he just immediately turned another 45 degrees.
15. Let’s Never Speak Of This Again
I'm cringing even thinking about this date and it happened about 12 years ago...So we went for food and a few drinks, it was going great, and we were getting on really well. We started walking back to the train station and I felt my stomach cramp. I must have eaten something that didn't agree with me.
I try not to panic and tell myself I'll go to the toilet on the station platform. We get to the platform and the toilets are out of order, the cramps and spasms are getting quite bad now and I'm starting to sweat a little. I'm trying to keep up the conversation with my date but all I can think is that I need to not poop myself in front of them.
The train arrives and we both get on, I can't bring myself to go in the tiny train toilet when I know it's going to be baaaad, so I make excuses to my date and say that I have to head home instead. My stop was only a few in, so I quickly say goodbye and exit the train.
The cramps, sweats, and pain are horrendous by this point, so as I exit the train I pick up my speed and do a jog/shuffle across the platform. I trip over my own feet and land on the platform concrete. The impact of hitting the deck belly-flop style meant that everything I'd been holding in came out.
I mortifyingly looked up to see my date staring out of the train window, looking at me as the train passed. We never called each other, we both knew what went down at that station.
16. It All Came Crashing Down
This happened to a close friend. Her date brought her to the local rock-climbing gym which he frequents. She said she'd climbed before and seemed pretty fit.
She fell and broke her arm within a half hour of being there.
17. Licky Licky
I met this guy at a coffee place. He was nice and we met for coffee once more and then met for dinner at a bar. We were sitting at the bar, and I had turned to get the bartender’s attention. He leaned over—and did the unthinkable. He straight up licked my face, from chin to temple. I was visibly shook.
So he tried to playfully poke me to tone my "what the heck" face down and I asked him to stop. He then leaned in and whispered, "I'll just poke your sleeping body later"…I made him leave. I walked him to his car and had a bouncer stand by the door and wait for/watch me.
I received several messages a few days later. He was concerned he hadn't heard from me and was going to "stop by my parents later to see if I was ok”. I never took him to or spoke to him about my parents’ house/address. I told him I would call the authorities if I ever heard from him or saw him again.
Thankfully, I never heard from him again.
18. Signs From Above
We went for a walk, got a bit frisky rolling down a grassy hill, and just went at it right there behind a Mormon Church. First, a Mormon spotted us and told us we can’t do that there and just creepily watched us get dressed.
So we went elsewhere, at which point we both complained about not finishing. And the next spot we chose ended with about 30 mosquito bites on my behind, two on my junk, and she rolled over onto dog poop and cried that it was only on her.
"Go get a room," God said.
19. Money Matters
He took me to an Italian restaurant. After we ordered he got a phone call. He makes a small chitchat with the person on the other line. Then he says, “Mom, I know, I ordered the cheapest thing on the menu. Mom! I'm here with my girlfriend. I'll tell you how much the bill was afterward”. Two things wrong with that.
One, it was a first date, and I was NOT his girlfriend. Secondly, he lived with his mom (fine…I can deal with that) and his mom micromanaged all of his money—to the point of calling during dinner to see what kind of money he was spending. It was super creepy and really weird.
I saw him one more time to confirm he was a strange ranger and broke it off.
20. Running Him Ragged
I was the cause of a bad first date. I grossly underestimated how long it would take him (I’m a woman) to hike seven miles. I had to call a friend to get the ranger hotline to let them know we would still be on the trail after 9 pm when the gates closed.
By the last three miles, he was giving pep talks to his legs and threatening to eat the frogs that were hopping on the trail. I had to use my phone to light his way because it was super dark and he didn’t have his. Sorry, dude. You were a really nice guy. I didn’t mean to walk you to the point of collapse.
21. Drink Up
I met a girl online and we started talking. Everything was grand. She and I texted often and seemed to be hitting it off well. So we meet and start having dinner. Everything is good except she just seems a bit off.
We order a pitcher of margaritas. We each have one and mid-sentence she just stops talking and stares at her hands. Just...looking at them. I ask if she's ok and she says, “Oh, I'm sorry, I'm just really tipsy”. I say “Really? We've only had one drink”.
She says then, “Oh, I've been drinking all day”. Now, I stop and think about past conversations. She texted me a lot saying, "Hey I'm a little tipsy walking home, keep me company”. I start thinking this might be a trend with her. She then proceeds to faceplant into the table. I think she's joking because it was so exaggerated.
I laugh and realize she isn't moving. I tap her and wake her and I call for the check, which was a looooot more than I'd figured. She then asks if I could walk her home. I said I would as she was in pretty rough shape. We start walking more and more and then I ask how much farther. She says another mile.
So we walk some more and finally get to her place. She offers me some water and then asks if I want to stay. I politely declined and she angrily kicked me out. So, that was that. I had to use a GPS to find my way back to my car.
22. Drama King
This is technically a breakup, but it happened on a date. I tried to break up with him in private in the car. He said he needed a pause on the conversation, took us into a restaurant, then proceeded to burst into tears in front of everyone.
The best bit is that a few weeks later, he came into my work pretending that we hadn’t broken up and I had to break up with him again...while he cried...in front of his sister who was my co-worker...
23. Telling Tall Tales
I got the friend call bail-out one time. The girl had to go to the bathroom right in the middle of the date so I knew it was coming. She kept talking once she got back for a few minutes. Her story was rather impressive, though.
She didn't stick me with the “my friend needs help” act. She told me that a bus crashed, and she had to get back to the hospital because there were multiple deceased kids. That was interesting.
24. Good Enough
My first date was my worst date. After an excruciatingly long car ride listening to him discuss his love of clubs and bottle service, we get to the restaurant he refers to as "enough of a hole-in-the-wall for a girl like me”. After ordering he says he needs to check his bank account, followed by him telling me to cover dinner (I'm fine with paying, just maybe ask politely).
Then he, and only him, spoke for the rest of the dinner, explaining how the earth is flat and he is going to be a senator on Mars in 10 years, so any woman who seriously dates him will need to be supportive. Afterward, since he drove, he dragged me to a club.
Upon him uttering, "This is going so well!" I explained to him that it, in fact, was not, given that I had yet to even have the chance to speak. He then asked him to list examples. After saying this was the worst date I ever experienced, he sat down next to me and asked, "So we can be friends who possibly become more?"
I promptly called an Uber. He texted me asking me on a date every day for a week straight until I finally blocked the number.
25. Shortchanged By The Universe
I arrived early at the coffee shop because I was nervous. When I parked, I realized I forgot my wallet at home. Mind you, the coffee shop was 30 minutes from home, and we were supposed to meet in 10 minutes.
So I scrounged around in my car for loose change. Found $2 in quarters, nickels, and dimes. I hurried in and bought the cheapest coffee I could. She comes in, confused that I already got something, and orders her own—very gentlemanly of me not to offer to pay with the rest of the nickels and pennies in my car, right?
We sit outside, with the setting sun in my eyes, but I'm too proud to move so the sun is blinding me the entire hour we are there. Honestly, the conversation was pleasant, but at the end, I shifted my weight on this wooden chair I was sitting on…and heard a loud CRACK.
Sure enough, the chair was broken. I know I’m a large dude, but this just had to happen now? I wasn’t surprised when I didn't get a call back from that date.
26. Well, That One Backfired
I haven't had many dates but the worst—and funniest—was from Tinder. The plan was to start at my house as a double date then, and if it went well, we'd split up and go out.
It never got to the last part because he took a dump in my toilet, blocked it with toilet roll, got embarrassed when my friend went in, and left. Oh, and he forgot his jacket in the rush so got one of his friends to come and get it the next day.
27. Dr. Yuck
I ask what he does, and he says, "I don't like to brag about my job, you know the fact that I save lives every day”. He was a doctor, and he said that with no sarcasm. Then he gets angry because he asked me out on a dating app five years before our date and I didn't respond to his message immediately.
I tell him it was an old account I never logged into he says, "Goes to show girls are so fickle…” And the icing on the cake? He admits he actually has strep throat and "I actually shouldn't be on a date right now”. Gross.
28. Third Time’s The Charm
In my sophomore year of high school, I wanted to go see a movie with my date. At the first theater, they asked for ID for the first time ever. I wasn’t 18 and couldn't get tickets. At the second theater, the movie was canceled after the AC broke and the heater reached 95 degrees.
The third theater didn't have seats next to each other. She still wanted to watch it, so we sat in DIFFERENT ROWS. Unsurprisingly, there was no second date.
29. A String Of Bad Luck
There's honestly no way for me to say which date is worse. I've had many bad dates, but these really take the cake. I went on a date with someone that seemed normal until she revealed that she was convinced we were all part of the matrix.
Another person I dated was a biter. I had to go to work and see my family with scars and bruises on my neck because she bit and yanked. I thought I was gonna die. And one date abandoned me at a club because I was out of my introverted comfort zone.
I walked home, then ended up peeing my pants because I was wasted and didn't really care as I was going through a depressive episode. So, as you can see, my dating life has never been easy.
30. Is That My Ride?
I once was asked out by the mate of some friends. He asked for my number and called to ask me to dinner. He asks if I mind if he picks me up in his work vehicle. I have been in the corporate world for a while so I'm thinking it’s a company car, zero drama. Looking back on it, I realize I should have asked what he did for a living.
The night arrives, he turns up...in a garbage truck. But wait, it gets better. I decide “Ah well, he did ask and I said yes”, so we go out for dinner. I can only assume he was insanely nervous because he proceeds to get inebriated—to the point that he asks me if I can drive the garbage truck home.
Now, this thing has four gear sticks. I can only drive an automatic. So this numpty drove me home, in a garbage truck. Then asks if he can stay the night.
There was no second date...
31. Playing With Fire
My first date was definitely my worst date. The girl started lighting matches, would put them out with her fingers, then eat the burnt matchstick head.
32. Just Watch Me
My worst date was at boarding school, on a college campus. We were both straight-edge dweebs, so we went to a party at the student center together. He got bored in about 15 minutes, so we snuck off into the building together. I thought it was gonna be for some, like, making out and stuff? No.
He found a computer lab and made me watch him play League of Legends for two hours while he tried to explain the game to me. If you meet a hot guy and he's single there is probably a reason.
33. It Was Like Watching A Car Crash
Online, her profile picture was cute. We had about four or five normal conversations before we decided to go to the movies. Now, I hate taking dates to the movies because this minimizes conversations and getting to know somebody in person, but I was like, “She’s cute, what’s the worst that can happen”?
Now, let the record show she chose the time of the movie and what time I was picking her up, so it's not like she had no idea that she had to use the bathroom. The movie theater was about 15 mins from her house. As soon as she got in my car, she seemed intoxicated, threatened to kick-fight me if I tried anything funny. This all happened within the course of 10 minutes.
On the tenth minute she said "pull over," so I did. I couldn't believe what she did next. She got out of my car on a sort of busy highway street and proceeded to take a dump within eyeshot…it was one of those times where it's hard to look away. When my brain registered what was going on I leaned over, closed the passenger door, and drove away.
34. The Double Date Disaster
So for starters, this was my first date. First date ever. I had no frame of reference for this, but I had just turned 16 and the guy had been cute at school, so the bar was really low. He somehow managed to limbo himself under it.
I didn’t want to go on a date without another couple because I have no trust in people. He had a big friend group and I knew all of them, so he assured me this wouldn’t be a problem. When I got to his house, the person he’d asked to double with us was...his aunt, who he apparently lived with.
She was 21, I was 16, already great. Her date showed up and he was not aware it was a date. He thought they were just hanging out, not chaperoning her awkward little nephew and his new love interest. He was Polynesian. She made Hawaiian haystacks.
He’d never seen those before, but he walked into the house to the scent of badly burned rice because she couldn’t cook. He saved the rice, everything else was straight out of a can, it was great. They hadn’t planned anything, so they decided to throw blades with us in the backyard.
I did better than my date, he was upset, then his aunt nailed him in the behind with an airsoft BB and he was REALLY upset. To salvage things, his aunt suggested we go bowling. I was wearing ballet flats, so I had to wear his weird too-big 2010 teenage nerd socks, which I already had too many questions about that I didn’t want answered.
So we headed out to go bowling, but not before he tried to reclaim his teenage masculinity by squashing a spider on the wall... by kicking it, and kicking his leg right through the wall along with it. His leg got stuck. His aunt had to help him. I was not impressed.
Finally, we get to the bowling alley and walk in and we’re all really good…but then it gets really awkward because the manager is his aunt’s recent ex. So eventually the date ends, and he tries to kiss me in the back seat of his aunt’s car with both the aunt and her date watching. She cheered.
I’d like to say that I didn’t go on another date with him, but this wasn’t even the worst date I had in high school.
35. Taste Test
He stuck his fingers in my dessert, licked his fingers, and did it again!! I ordered a lemon meringue pie and offered for him to try some. He said “no” only to then proceed to say, “Actually, that looks good". Then he sticks his fingers in for a taste. Yuck!
36. A Night To Remember
Back in the day, I was on extended leave and was going through some rough times. So I went to Colombia to learn Spanish. I was out with some guys from the Spanish school and spotted this absolutely stunning woman. I knew I had to ask her out, even though my Spanish was still pretty basic.
So, I went ahead, asked her out, and to my surprise she said yes. One day later, the day of the date, I didn't feel so well but I decided to go ahead, I was so excited. So I went there, picked her up and we went to a nice restaurant. Afterward, we went for a walk on the beach—yep, sounds cheesy but it's true.
Right then, I started to feel really bad, becoming dizzy and all. That’s when it happened. I had to throw up—not normally, but with all the power my body could give. I don't remember lots about it, apparently, I fell unconscious and woke up at the hospital.
To my surprise, my date was sitting right next to me, in training clothes since I puked all over her. She was really worried and just said that we hadn’t had the chance to finish our date. This year, we're getting married.
37. He Got Gassed
My worst date started as a total high school thing: a girl wants to set up a date at her place while her parents are gone for the weekend on vacation or something. So I agree to it, we're having a good time, everything's going well.
It’s starting to get late, we're in bed together, and she totally passes out. She’s out cold, snoring, it’s like 3 am and I'm still awake. Then, she starts moving around on the bed a little…and she lets this toot rip like I've never heard.
It started and it just kept going....and going. At first, I thought maybe it was her little old dog. It wasn't...then it hits me and oh my god, it’s so rank. I pull up my shirt to cover my nose like a mask and in my mind, I'm thinking what the heck did she eat?
To top it all off, she then made this little noise of relief when it was finally over. I couldn't take it. I slipped my pants and socks and shoes on real gently so as not to wake her. As quietly as possible I walked out, down the stairs, and right out the front door. Luckily, she lived in my neighborhood and it wasn't a long walk home.
Of course, the next day she asked me where the heck I went and why but I didn't have the heart to tell her, I figured it would be too embarrassing.
38. Three’s Company
I’m taking a girl to the movies and she asks, "Can my best friend come too?" There goes my chances but trying to be nice, I say, “Of course you can!” She shows up with her friend, who is indeed a guy.
This is when I find out that it’s her one and only ex, but they remained best friends and nothing is happening between them. I think, “Well, this date is ruined, but let’s try to salvage it". I go to pay for our tickets (mine and hers), even when she offered to pay for hers.
After buying, she turns around and buys her ex’s ticket…We actually got along fine and they were nice people, but it was like a tug of war for the rest of the night fighting for her attention. Of course, I lose since they are best friends.
When I get home, the guy adds me on Facebook, and he proceeds to tell me don't bother trying to date her, she's a terrible girlfriend. I finally got her alone for one more movie, but it all just sort of fell apart. I actually really liked her, but clearly, I had no effect on her. Oh well, I guess.
Take note, future daters: movie dates are a bad idea.
39. Clownin’ Around
Perhaps not my worst date, but definitely the weirdest. I was on a date with this girl who seemed great: good-looking, funny, shared similar interests. It was our first date, and we were sitting in some bar that she's a regular at, discussing ourselves when it starts getting to the basic first date questions.
"So, you said you work in an office but is that what you really want to do?" I asked, "Did you go to school for it?" "Actually…” She says, reaching into her bag, "I'm currently going to clown school”. I kid you not, this girl had pulled out a red freaking clown nose and put it on.
Now, if this was our third date, I would have been less shocked. However, we had been talking for a week and this was the first date—we were supposed to IMPRESS each other. But she was good-looking, and I wanted to hook up.
So I said, "Oh! That's so cool. I didn't know clown school was actually a thing”.
"Oh, no, it's competitive!"
"I had no idea. So, are you in clown university, clown college, clown technical school?"
And then she took my joke as an attack. For a clown, she had a terrible sense of humor.
40. Equality At Any Cost
I went on one date with a guy I wasn’t physically attracted to because he seemed nice. He spent the ENTIRE date bragging about how much money he made. We shared a pizza. I had one slice, he had six.
When the bill came, he said he’d appreciate it if we split it evenly “because that’s how things work these days”. He tried to make out with me when he dropped me off at home and my god, his breath... it was like he ate a dead raccoon.
41. Got Milk?
A few years ago, I went on a coffee date with a nursing student who described in vivid detail how he and his ex-girlfriend milked an old lady into a toilet at a party. According to him, that was not even the first time or party where he had milked her, he just happened to do it with his girlfriend that time.
I was mortified and found an excuse to promptly leave. The funniest part was a few days later when he texted me asking to go on a second date—which I ignored—followed by another text the next day that said, "It was the milk story, wasn't it?"
42. An Awkward Introduction
I got stood up at a cafe. She called and told me an emergency had come up and she wasn't going to make it. I had only been waiting for three or four minutes and wasn’t too upset about it, so I called a friend to see what he was doing.
I ended up meeting him across town at the bar he was drinking at, which is also where he introduced me to my date, who he had just met playing pool there.
43. An Icy Encounter
Back in college, I was invited to an ice rink with a girl I liked and some of her friends. I did not know how to ice skate and I did not pick it up very quickly, but I wanted to try and impress her somehow. Well, I hugged the wall the whole time and made a fool of myself.
The highlight was when I saw a flash of light as I fell in front of a group of people. Turns out I had fallen right at the moment someone took a picture, so my failure was immortalized forever. She took me back to my apartment and ended the relationship before it began. But there's a silver lining.
The woman who is now my wife was at that ice rink on that night. We didn't realize we were there at the same time until a year or two into our relationship and she exclaimed, "You were that guy who couldn't ice skate! Yeah, she didn't seem that into you”.
44. Bragging Rights
On our second date, he bragged to me: 1) how long he was able to stay on unemployment, 2) how he was always able to talk his mom into letting him come home after she kicked him out, 3) how he basically paid for the $3,000 implants of a dancer, even though he didn't get anything for it.
He also revealed that he got locked up for about four months for pulling a pistol on some teenagers, but he didn't intend to use it. This was a half-brag, not a full brag. It was so strange because he seemed like a nice guy on the first date.
On the second date, with all of that, I was just laughing inside and wondering how I was going to end the date. Turns out it wasn’t a problem because after dinner he had to go and hang with his buddies at the video store.
45. Laying All Her Cards On The Table
My worst date? She had Crohn’s disease. She takes her pee bag out in the middle of our dinner date and says I need to look at it so I understand what I’m getting myself into. The catheter tube knocked over her drink. It was awful. Poor girl.
46. Momma’s Boy
For our first date, he took me to dinner at his mother's…with his brother and the mother’s crazy housemate. After dinner, we watched Iron Chef with all of them while sitting on the floor because there weren’t enough chairs. During the show, his mother was talking to us about using vibrating toys when doing the housework to make it more enjoyable.
And here’s the best part: He didn't even live with his mother. Needless to say, it was our first and only date.
47. The Ole Switcheroo
My worst date started off as a date and ended up as an MLM pitch. On the plus side, I still have those Cutco scissors and they are decent.
48. The Stench Of Success
It was my third date with a girl, and we went to a Poison-Def Leppard concert. We weren't eating before the concert and I was starving, so I grabbed a chicken salad sandwich from a gas station before I picked her up.
Halfway through the show, I have to poop. Bad. I run to the can and every toilet is knee-deep in filth. We had VIP seats, so I figured I would wait and hit the VIP bar on the way out. I took a massive dump and made five guys scream about the stench, which made me giggle.
Well, we parked in front, pulled the car out, and sat and waited. All of a sudden, round two hits—and this time it is wet. I was getting stomach contractions every 2-3 minutes, I was death-clinching the steering wheel and sweating like a fat lady in Golden Corral.
I then had an epiphany that if I just tooted a little, I would feel better. Oh, how wrong I was. The soft serve ice cream machine in my shorts exploded and got everywhere. I ran into the woods, finished pooping, and wiped my butt with my wifebeater.
We have been married 12 years now and have three kids.
49. Didn’t See That One Coming
I was 19 or so, sitting at a bus stop bench waiting for the bus to go to work. This stunning woman sits next to me. Not long after, she starts talking to me. We have a pretty good conversation and I build up the courage to ask if she'd like to meet up sometime at a nearby coffee shop.
She says YES! We agree on a day and time then the last thing she says to me before I get on my bus is "It's a date”. I go to the coffee shop at the agreed time and see she is already there. But that's not all. She also has a male friend sitting right next to her.
No big deal, I figure he must be there in case I'm a creep or something. I sit across from her and we order a drink. Then right away she says, "So, what do you think about Jesus,” and pulls out a pamphlet. I reply, "I thought this was a date," and she says something along the lines of "I didn't think you'd show up if it wasn't”.
I ended up leaving right away before she saw me tear up. That was definitely my worst date ever.
50. Just Pop A Squat
I was in France and having a lovely dinner at a sidewalk cafe with a young lady I met the day prior. But in the middle of our dinner, she did something utterly deranged. She excused herself to use the restroom, got up, walked about ten feet, squatted, and peed in the gutter. Yup, no second date after that.
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