21 Awkward And Funny Dating Stories That, I Kid You Not, Actually Happened To People
"He told me I looked different than what he expected, and offered me gas money to leave."
So here are some of funniest and most awkward dating stories from the 2010s:
1. This shocking party treat:
"I met up with this guy on Tinder and we seemed to click. Fast forward into the date and he disappeared and came back holding a sandwich-sized bag half full of what looked like broken glass. Crack, my Tinder date had crack. I politely declined his offer and then when I had the opportunity, made an exit."
2. The butter knife bandit:
"Things were pretty normal during the first half of the night, but then things got weird. He sat next to me in the restaurant booth and proceeded to slide a butter knife up and down my thigh. He then went on to ask what my response would be if he told me he had five dicks. Yeah, never saw that guy again."
3. This absolutely awful first date:
"Instead of rescheduling, one guy took me to a funeral on a first date. Then afterwards, while eating dinner, the conversation was so awkward due to nothing in common, I couldn't even look him in the eye."
4. This very cool mom:
"An older woman I used to work with decided to set me up with her son. He asked if I'd like to come over for dinner. This is not normally something I would agree to, but I did since I knew his mom. Turned out he still lived at home with her. While I was planning my exit strategy, she got up and asked, 'Would you two like some privacy for coitus?' I thanked them for a lovely meal and made up a lie about how I had to leave. I never felt comfortable around her at work again."
5. This unexpected ~kinky~ date:
"I agreed to meet up with a guy I knew through mutual friends. We decided to drive around for about an hour, just talking and getting to know one another. It was going well so we started making out. He then whispered to me, 'Would you pee in my mouth...with a funnel?' Luckily my cousin texted me and I said I had to leave. As he got out of the car he asked me how much I usually pee so he could go buy me a funnel at the store. I blocked him as soon as he got out of my car."
6. This shitty date:
"We went to sushi and he just had to go back to his place before drinks. Turned out we had to go back to his place because he was afraid of public restrooms. I sat alone in his living room listening to him straining while trying to poop. He then realized he was out of toilet paper and texted me to grab him a roll from upstairs. Let's not even get into the smell. Literally the shittiest date ever."
7. This...unusual break up:
"I had been dating this guy and was really falling for him. He said he wanted to plan everything for our Valentine's Day date. He loved astronomy, so he picked a spot and brought a small telescope and showed me all the constellations. I was on cloud nine. I changed into something sexy and invited him in. He got undressed, got in bed, and then told me he couldn't do this anymore. He basically got undressed to break up with me. He said I deserved a really nice Valentine's date before he did it."
8. This date that ended in the ER.
"This guy I met at a bar took me to a Chinese place for dinner. We ordered a bunch of different things and shared it all. My face started to get really red and I broke out in hives. By the time we got to the car, I was struggling to breathe and I asked him to take me home. Well, I went into full blown anaphylactic shock and stopped breathing in the car. Apparently I was allergic to almonds and didn't know it, and we ordered almond chicken. He had enough sense to take me to the ER. I woke up a few hours later to him sitting in the corner of the room looking horrified and apologizing profusely because during all the commotion they ripped off my shirt and bra and he saw my boobs. Once my roommates got there he bolted never to be heard from again."
9. This cemetery excursion:
"I went on a double date with a friend, and the guy who was my date thought it'd be cool to go to a cemetery. So, we walked around and talked, but when we went back to the car, he realized he dropped his keys. We all had to walk over and around graves to find them."
10. This over-sharer:
"The guy who asked me out worked at a garage but he didn't bother to shower before our date, so he showed up covered in grease. The whole night was awful, but I eventually gave up after he said, 'You ever hang out in hospitals? I like to. Maybe just because I'm turned on by blood.' I cannot make this shit up."
11. This Tinder mishap:
"Not only was the guy I met up with not the person in his pictures, he told me I looked different than what he expected, and offered me gas money to leave."
12. The clumsy Superman:
"He showed up dressed like Superman — white button-up over a blue Superman T-shirt, Clark Kent hair, glasses — and took me out to sushi...thought I told him several times that I was a vegetarian. At dinner, he spilled sake all over me. He also pulled out his digital camera to show me photos of the trip to Europe he had taken with his mother five years ago. And then, while he was driving me home, he told me his goal was to have a relationship like Leo and Kate in Titanic."
13. The forgetful date:
"I was on a date with a guy from Tinder, and towards the end he asks me if I want to see his neighbor's new puppy. So he calls them and says "yeah me and Stacey will be over soon."
We just spent three hours together and he didn't know my name was Perry."
14. This educational date:
"My date picked me up and drove us to a restaurant. When we got there he grabbed his backpack, which I thought was strange. He then specifically requested a table next to an outlet. I soon found out what he needed his backpack and outlet for. I kid you not, he pulled out his laptop to show me a PowerPoint presentation on a pyramid scheme he wanted to recruit me for. He spent the entire date trying to recruit me."
15. This first date that moved suuuper fast:
"I had had my eye on this guy for a while. After a few weeks of flirting he finally asked me to go to a gig with him on a date. We went to the gig and were having a good time, when suddenly HIS PARENTS SHOW UP! Turned out he had invited them because he wanted me to meet them....ON OUR FIRST DATE!
Afterwards he called me continuously and I asked him to back off but he didn't, so I called it off completely. This ended with him begging me to change my mind by screaming 'I'M A COOL PERSON!'"
16. This nasty date at the lake:
"I allowed my friend from college to set me up on a date, which ended up being a group date out on a lake. My date, Austin, was plastered by the afternoon and we all decided to go for a swim. At one point during the swim he got very quiet. The group looked in his direction, and we noticed his face looked like that of a constipated child. His friend yelled: 'Get in the boat, now!' Moments later, we saw a very large turd float to the surface next to Austin. Austin laughingly got back in the boat and acted as if nothing happened."
17. This uncomfortable dinner convo:
"I coincidentally went on a date with a woman who worked in the same field as me. She knew of my boss and went on and on about how hot she was. I didn't have the heart to tell her that I worked for my mom's company, meaning my date was actually talking about how hot my MOM was for the entire date."
18. This Valentine's vomit:
"Once in high school, I was asked out on Valentine’s Day with a big teddy bear and roses...the whole shebang! However, I had nausea that morning and threw up all over the guy and the gifts. Oops!"
19. This buck naked BBQ:
"I met a guy on Tinder and went to his house for a barbecue. He proceeded to get high and then streaked around his backyard. I went home and never spoke to him again."
20. This catfisher's logic:
"I got catfished by a girl pretending to be a guy at the very start of high school, and she tried to tell me that if I could like the guy I could like her bc all of his traits were actually hers. We didn't talk much after that."
21. And lastly, this series of unfortunate events:
"We went to the beach with a few friends. I drank a little too much and was giving him a blowjob while driving, and he crashed into a tree. Later that night I threw up all over him. My friends don’t let me live this down ever."
Submissions have been edited for length and/or clarity.