As you might have noticed from our recent posts, we know that life can sometimes feel extra heavy right now. Sometimes, the best antidote to when it hasn’t been your day, month, or year (s/o to Friends) is just a good, solid laugh at something that didn’t happen to you – so that’s what we’re here for.
We’ve all had our fair share of dating fails, and it got us thinking…What’s the weirdest thing to happen on a date? So, we asked our members, our co-workers, our friends, and our friends of friends to think back into the depths of their dating history and dig up those funny, strange, outrageous, or just downright weird stories and share them with us. Some will make you gasp, some will make you giggle, and some will just leave you scratching your head thinking “what did I just read?” Whichever way it goes, we hope you enjoy them.
Chapter 1: A Little Weird, With a Sprinkle of Awkward
“Guess You Don’t Get by With a Little Help From Your Friends” – By BCGal45
“In high school, I went on a date with a guy who I’d been friends with for a long time, but it had recently turned into something more and it was our first official date together. It was a small town, so as we were headed to our table, we ran into a group of people we know. One of the guys said, “Hey! You guys should join us! Unless you’re on a date…” Without asking me, my date goes “oh no, we’ll join you,” and we had dinner with them. Ummm excuse me, we *were* on a date and I didn’t want to sit with them! Safe to say it was not the night I had imagined.”
“Aphrodisi-what?” – By GW
“I was out on a dinner date and after we sat down, the owner of the restaurant came over to our table to explain that everything we were about to consume was an aphrodisiac. Super awkward for a first date, but even more awkward when the owner continued to tell us in between each course. They even yelled at us for not eating the chicken bones… needless to say the “aphrodisiac” effects of the food did not hold up”
“Are You Pho Real?” – By RJ2000
“I went on a date with a girl to a pho place and she got mad at me because she was eating the bean sprouts before the pho arrived and after suggesting I do the same, I said “nah I’ll just wait for the soup.” She gave me the cold shoulder the rest of the date for not eating the sprouts with her. I was just trying to eat some bean sprouts with my soup!”
“You’ve Got to Be Kid-ing” – By Alx9034
“I went on a date with a guy for drinks and about an hour or so into it, he dropped the bomb that he had a son…who was 10 years old! He went on to say the son lived in Mexico with his mom, and the story kept getting more convoluted and he started getting very emotional about it. I guess it was obvious on my face because when he went to the bathroom, the bartender started talking to me about how strange the date was.”
Chapter 2: Ex Marks the Spot
“Uninvited Guest” – By DJ56
“I brought a guy I had just started seeing to my hometown to meet my parents. We went out to dinner (just the two of us) and as we sat down I noticed my ex was at the table beside us, he came and sat down with us for 20 minutes…. Then after he finally left the guy I was with said “he seemed super nice, was he a friend from school?” No comment…”
“Fancy Meeting You Here” – By TJ1980
“I showed up to a date with a girl and I kid you not all four of my exes were at the same restaurant at the same time… I wish I was making this up. I spent the whole night sweating and couldn’t even come close to focusing on the date I was on – what are the chances?”
Chapter 3: Swing and a Miss
“Young Love” – By JML
“I had my first kiss when I was 17. I was pretty nervous but he seemed confident so I just let him take the lead. He tilted my head back to kiss me, and instead of the romantic first kiss I had imagined in my head, he kissed the side of my mouth and said ” I always miss.” Not the line I was expecting…”
“Do You Mind Stepping Out of the Car Maam?” – By BigR20
“I was driving a girl home from a date and as we pulled up to her place, she refused to get out of my car because she wanted to hook up. I tried to nicely tell her I wasn’t interested in going that far, but she kept trying to kiss me so I told her more firmly that I wouldn’t be going inside her place. Eventually, I had to get out of the car to remove her from it.”
“Three’s a Crowd” – By 91Gal
“A guy I was seeing invited me over, and when I arrived I realized he had invited another girl at the same time… he clearly wanted a threesome but had not talked to either of us about it. Awkward.”
“A Bold Ask” – By Anon98
“A guy invited me to his friend’s birthday orgy a few days after our first date. I think that’s all that needs to be said. I didn’t go… just to be clear.”
Chapter 4: Full-on Cringe-Worthy
“What Was That Bump?” – By Greg5896
“I was on a date driving us in my car to downtown Portland when I came around a corner and hit a dog. I slowed down a little but it was very dark out and it was a very busy road with nowhere to pull over so I just kept going… She didn’t talk to me for the rest of the car ride, though surprisingly, we still dated for another 6 months or so. I still feel pretty bad about it… What a way to start a date.”
“Bad Doggy” – By Eron78
“I was going to cook dinner with a date but we were missing an ingredient, so we went to the store to grab it. As we were leaving, I noticed his roommates’ dog come out of his room, so I asked if we should put any of the food that was on the counter away. He assured me the dog was “super chill” and wouldn’t go near it. When we came back, the dog had not only eaten every single ingredient we’d left out, including the comically large wheel of gouda cheese, he’d also thrown it up all over the kitchen floor. My date asked me to clean it up because vomit grossed him out …. talk about a spoiled appetite.”
“Why I Can Never Go Back to Anytime Fitness” – By ABgurl45
“I once went on a date with this guy who was really into working out, I didn’t go to the gym much myself but thought I would humor him when he asked me to come to a workout. We got into the gym and he asked me to help him with his bench. He lay down and as I was getting ready to spot him he very insistently shook his head and said “no, hop on” and I suddenly realized he wanted to bench me instead of the bar in front of the whole gym…. I’m ashamed to say I let him do three sets”
Chapter 4: Talk About a Red Flag…
“Dr. McCreepy” – By BG234
“I was chatting with this guy over text and when I asked what he did for work he said he was a dentist. A great job is always a good start, but then he asked me if I would send him pics of my teeth. When I didn’t respond right away, he followed up by asking if I had any fillings, and what color they were… I was so creeped out I never responded.”
“But It’s Organic!” – By ItsMe789
“So I went on this date with a woman who was super into fitness and all-natural products. We went to her favorite smoothie bar for our date and mid convo she just starts applying her green smoothie to her face. I didn’t know whether to ask, avoid, or just pretend like nothing was happening.”
“Why Do I Feel Like We’re Being Watched?” – By ItsmeNJ
“I went back to a guy’s place and as we walked through the door, I noticed he had a table FULL of miniature figurines that he painted. It seemed a little weird, but I decided to give him a chance. We sat down to watch a movie, and he turned all the figurines around to watch too! That was officially too much… I quickly made up an excuse to leave before he could tell me all of their names.”
“Hamtar-no” – By Anonymous90
“This guy and I had gone on a great first date and I was so excited for the next. I showed up at his place as we were going for a coffee and walk and when I got there, he had his pet guinea pig suited up for the walk…leash, harness the full works. We walked his guinea pig for the block that it could make it with its tiny legs and obvious horror that it was outside. The date ended there and it was our last.”
