27 Unbelievably Bad First-Date Experiences

One guy brought his mom
27 Unbelievably Bad First-Date Experiences

A lot of first dates result in incredibly haunting memories that people would rather forget. For instance, there’s someone out there whose group chat keeps reminding them about the time a guy brought his mom along on their first date. You know for a fact that every time that person went on another first date after that, their friends asked, “Was his mom there?” and laughed uncontrollably at them. That’s the kind of sick world we’re living in. 

To that end, Redditors have shared some of the weird, funny and downright unbelievable first dates that have continued to haunt them over the years. A word of warning: If you’re single, these stories won’t instill even a shred of hope for your dating future. 

cecikierk 2y We were in a fairly empty lounge. There was a TV on with either Jay Leno or Conan O'Brien monologue on. Instead of either chuckle along or ignore it like normal people do, he decided to dissect each joke and why they are not funny and people shouldn't be laughing at them. Не then proudly said he does it at parties and comedy shows too. People often sarcastically say someone must be fun at parties. I have never met anyone actually admitting to it. ... 158
BBVIP21 2y Не insisted to take me out on a date, and so for dinner he suggested a sushi place about 30 mins away from our area (we both live on the same side of the city). When it was time to pay, he forgot his card. Alright sure, no problem, l'll pay. I don't mind. But for the first time ever, I did not have my card either. LOL. We then told the servers that we'll be back to pay (I left my license with them). So he drove alllll the way back to our area, drove pass HIS
MidnightFireHuntress . . 2y Met a guy on OkCupid (I was 24 he was 25) Не brought his fucking MOM to the date, she dropped him off and then sat with us for lunch, it was so awkward, she was nice and everything but he would text me things DURING THE DATE like She's my best friend, please don't be mad It was so freaking awkward the first thing I did when I got home was laugh so hard I could barely stand. ... 98
SleepFlower80 . 2y OF I got set up on a blind date. We were texting for a bit before the date but this was before camera phones (I'm so old!) so we weren't able to swap photos or anything, so I literally went in to this date blind. He'd told me he was 6' 2 so I was expecting a giant given that I'm 5'. The man that rocked up was shorter than me but he accused me of lying about my height. It was the most surreal conversation I've ever had on a date, and we didn't even see out
zerolinks2014 . 7y My name is Andrea, his name was Sam. I though he was a girl, he thought I was a girl as well. Realised we were 2 dudes and said goodbye to each other.
rift_in_the_warp . 7y She talked about her extensive machete collection and how she's threatened some of her ex's with them just for fun. She also talked about how she got the massive scar on her arm for punching out a window. Her friend just sat awkwardly the whole night and got hammered. I felt bad for her since she didn't like being the third wheel. Here's the fun part though, since I was bad about ignoring red flags at the time, I tried to organize a second date. However she acted like she didn't know who I was and that
Flowersinhercurls 7y I go out to dinner with a guy I had only met quickly once before. First we go to dinner which is ok, nothing special. It was a little awkward. At the end of dinner he ask me if I like dance dance revolution. I was like uh sure why not. Не then proceeds to tell me he is really good at it and wants to show me. So after dinner he takes me to an arcade where he spends the next thirty minutes playing/dancing to dance dance revolution while I watch. Не never asks if I want
ConstableGrey 7y Back when I was extremely oblivious this girl said we should watch a movie together and I said okay. So she came over and we watched a movie and she left and I thought nothing of it. Then a few hours later I got a text from her saying Did you think that was a date? And then I realized, oh god, she thought that was a date, and in a panic I said yes and long story short we ended up going out for a year. ... 103
AbbyVanBuren . 7y Online dating: We met for coffee and walked the beach. It immediately started to not go well. We disagreed about almost everything. Не even mocked my religious beliefs. After walking a ways he asked if I wanted to sit on the beach. I couldn't believe he wanted this nightmare to last longer. I obliged. Не set his coffee cup down and it blew away but not far. I said oh no your cup blew away. Не looked, shrugged and ignored it. I litter all the time. Yeah, like if I have a bag of McDonald's trash, I'll
NineFeetUnderground, 7y So I went to a wedding once, and the groom set me up with this super hot Scandinavian bridesmaid. All going well & we move outside on a beach under the stars. Lovely stuff We start kissing, then she stops all of a sudden & says 'what's your lifetime ambition?' Out of nowhere. I don't have one. Certainly not one I can think of on demand with a raging hard-on, on a Norweigian beach. I told her it was a pretty deep question & hadn't thought about it. 'OK Mine is to touch a whale' she said, excitedly.
CowtheHankDog 7y I've posted this before, but it's a good one: I went out for coffee with a classmate. Не showed up half an hour late wearing baggy sweatpants with suspicious stains all over them. I had been amusing myself by doing the crossword while waiting on this guy, and when he arrived, he sat down and pulled my crossword over to him. Не looked at it for a moment and then said, Women who read are fine and all, but it isn't very attractive to show off. We did not have a second date. ... 159
glitterphobia . 7y This guy invited me ice skating. I'd never been ice skating before and wasn't very coordinated, but of course I didn't want to tell him that. We were skating for about 20 minutes and I was feeling pretty proud of myself for doing so well. Then, ВАМ! I totally wiped out and pulled him down with me, which caused him to elbow me in the face as he landed on top of me. My glasses broke, and I had a concussion and a black eye. I was too embarrassed for a second date. ... 17
skinnymatters . . 7y We went to see Human Centipede in the theater - at her request. The following three months were...brutal. 34
co-stan-za 7y First date with this guy, simple dinner and a movie. On the way home, driving down the highway, he decides to start driving 110 in a 65 mph zone. Не got pulled over and subsequently arrested. His mom has to come and drive me home. Needless to say, I never went out with him again. ... 14
Konebred . . 7y She was a bit younger than me and kind of lived out in the boonies. We went to a mexican place for dinner and somehow started talking about how spicy the salsa was. I guess she wanted to impress me by drinking the vial of salsa. ... 5
LittleBeauCreep. . 8y Showed up for internet based date. She shows up with a dude. Expected me to pay for them both to eat and drink for the evening. WTF? ... 1.4k
mkramer4. 6y I offered to pay for the bill.. she insisted to pay half. Didnt fight it, but only had a large bill so I pocketed her money and put my bill in. Anyway long story short I did the math wrong and stole 20 bucks from her. She sarcastically said thank you and I thought she was being sincere.. ... 3.7k
bacon_butter. 6y We order a small snack for our coffee and as it's arriving at the table he pulls out his Nokia phone. Trying to make a lighthearted joke I say MAN that has got to be the oldest phone I've seen in a while. really dug it in, trying to break that friendly wall. Well. Turns out it's not a Nokia. It was his insulin pump. ... 1.7k
Fridgecrisis 6y This was in high school. She invited me to her house to have dinner with her family, and I didn't know them very well yet. The conversation turned to names we thought were old-fashioned and ugly- sounding. We all threw out a few like Gertrude, Bertha, and Eugene, and then I said something like, At least that one's not as bad as Deborah! I used my ugly voice and everything. Her mom's name is Deborah. Her grandmother was also at the table with us. We've been married for almost 7 years! ... 2k
Oi_Kimchi . 6y I went on a date with a girl I met in an online chatroom to see King Kong at the cinema. I was in my young teens and the ending absolutely shattered me, even though I knew it was coming. I cried. Not a lot, but a couple tears. She noticed and asked incredulously if I was crying. I just nodded and without saying anything further she got up and left. Never returned any of my messages after that. ... 2.7k
Marrvveee . 6y Brought a girl out for sushi and unknowingly ordered baby octopus. Turns out octopus are her favorite living thing. ... 3.5k
steeltornado. 6y I didn't know it was a date and bought my little sister to hang out with her too. ... 934
Bluegunder . 2y At a restaurant i worked at, there was a white guy and a black guy on a first date. They were sitting in a booth and having a good time. White guy gets up to go to the bathroom. When he came back he sat in the wrong booth with a different black guy. Took him a minute to realize it was a different person. The person he was on a date with was not happy at all. They tried to salvage the date, but it didn't work. ... 2.3k
NotGreatAtSocializin 2y I told this guy I played the piano, and like half an hour later 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 to say, I left the restaurant fairly quickly. ... 13.6k
baconkiller1 . 2y I just really like mustard as she continues suck mustard packets worst part, we were at a somewhat nice restaurant. SHE BROUGHT MUSTARD TO EAT. ... 5.9k
irememberthepotatoho . 2y Mid date he placed his hand on my stomach and said My son will grow here. .. 17.5k jasmin_booklover . 2y Did you date Henry VIII? ... 4.8k
zDemon1c . 2y Went out with a girl one night and after dinner she drove me up into the mountains (I was new to the area) and 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 ... 7.1k
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