People Describe The Most Embarrassing Date They've Ever Been On
Image by Oliana Gruzdeva from Pixabay

I'm so over dating. I'm gonna die alone and I'm fine with it. I can't, I just can't even deal with the search for love anymore.

And I felt this way long before COVID. It is like having another career. There are so many nutjobs running amok.

And truthfully once and awhile, we are the nutjobs. How could you not be after living through date disaster after disaster.

As if just putting oneself out there isn't bad enough, most of the time dating itself all falls apart.

Redditor u/ExtremeSeason3708 wanted everyone to pour a glass of wine and dish about dates nights gone awry by asking:

What's the most embarrassing date you've been on?

After a really lovely beginning, the last date I went on, the gentleman across from me told me he had a small secret. No big deal, but he wanted to be honest. He was an ex-convict. I won't get into why, but needless to say, it was a bit much. It didn't go well from there. But we were both too embarrassed to leave.


Wake Up Reaction GIF by Originals Giphy

"It was one of those setups where my mom and his mom were friends and they were like, "our two nerdy, intensely introverted loner kids should date!" Unfortunately that was the literal entirety of what we had in common, so."

"Bonus detail: we went to a theater that was showing "The Big Sleep." He fell asleep".

- RosiePugmire

Chest Pump

"Organised a date with this gorgeous girl while I was at the surf club. Call for a rescue goes off and I'm running off to do my thing. Pull this older guy from the water, he is not in great shape and has stopped breathing. CPR and the whole works. 10 minutes later and the ambos take him away."

"At the date she wanted to know if I was gay or bi, had to explain what CPR was, that I wasn't attracted to the person and that it's to try and save a life. Nope, she wasn't buying it, I was was clearly gay for drowned men."

- CompletelyFlammable

Butt First

"My freshman year of college, I went on a first date with a guy from my Italian class. We had pizza and after dinner, we were walking around and it started to drizzle. I was wearing ballerina flats with no treads."

"I took a step on the wet cobblestones and my foot shot out from under me. I landed on my butt, hard. I was mortified, of course, so I stood up quickly. My date asked if I was okay. I remember saying that I felt queasy... and the next thing I knew I was regaining consciousness in the gutter."

"A woman stopped to help. I eventually got up and finished my date at the student health center. It turned out I'd broken my tailbone. I had to sit on a donut cushion in class for the next two weeks. It didn't work out. It's too bad because breaking my butt on our first date would have made a great " how we met" story."

- therapy_works

V-Day Mishaps

"This was embarrassing in the moment, but it worked out. It was a 2nd date, but it was also Valentine's day, so I decided to get her flowers, a card that plays music, and some chocolates. It was freezing cold, but I didn't have anywhere to keep them besides my car. I took the chance the flowers might die."

"We had a nice date, and when we get back to my car I got them out. Oh those flowers were DEAD. "Ah well...". She opened the card, and the sound chip just went bbbzzzzzzzz. I sighed and said "Well... I hope the chocolates are okay". She started laughing and gave me our first kiss."

- gh0stmanX

Best Excuses For Late Assignments That Were Actually True | George Takei’s Oh Myyy

Perfect Start

Season 1 Dancing GIF by FlirtyDanceFOX Giphy

"First date with my now wife, I got food poisoning and had violent diarrhea on the side of the road and had to clean myself with an old shirt I had in the back of my car."

- shirtlessin1stclass

See now, any gastric issues, I'd have to excuse myself and run into the shadows. So some of these people are stronger (or just maybe more adult) than I am. Also movies aren't a good idea until you're already a solid item.

All by Myself

Lonely Bucks Bango GIF by Milwaukee Bucks Giphy

"Girl and I made plans to meet at an outdoor mall and see a movie, this was back in middle school so my mom had to drive me in about an hour's worth of traffic, and she cancels 15 minutes out."

"I felt so bad for my mom driving me all the way there already so I simply pretended like she hadn't canceled, my mom dropped me off, and I watched a movie by myself. Almost cried but I kept it together. But I mean the movie was good at least."

- Lil_Sousa

In the Library...

"Valentine's Day at college. My boyfriend walks into the library and finds me studying. He presents me with a bundle of flowers and the most horrible gift I've ever seen… here's a pic."

"Well I had apparently joked about it while we were at target one day and so he bought it for me as a joke. It didn't fit in my backpack and so I had to carry it around my college classes for the rest of the day. Several teachers asked me about it and I was mortified."

"Well I still married him a little later and we've been together 6 years since getting married. Honestly it grew on me enough that I still have it to this day. It's supposed to be a toddler body pillow but it's just the right size for hugging while you sleep. He's asked if he can throw it away a few times but I won't let him. I've actually tried to find the damn thing a few times online but haven't been successful. Even after using its barcode and factory info. I figure it's getting pretty gross and soon I should let it go."

- Zetta216


"First date with my now husband. We are both very anxious people who had little experience with dating and we were both so nervous. I threw up right before the date. He came to pick me up and we drove to the library where we were planning to use their wifi to watch Netflix in the back of the car (despite being almost 20 years old, my mom would not let us hang out in my bedroom at home)."

"As soon as we got to the library he got out of the car and threw up in the parking lot. I then admitted to him that I had also thrown up right before the date. He tried to play it off as us having the flu or food poisoning but we both knew it was really just the nerves."

- cittegirl

Hey Dad!

"I went with a girl to see a really late night theater show. It ended at like 2am, well past when public transit stopped running. We didn't have a car or money for a taxi so we walked back to her family's house since I lived much further away. We collapsed fully clothed on her bed and instantly fell asleep."

"Three hours later her dad shook me awake and demanded to know who I was, then when he found out I was studying chemistry in college he started questioning me about thermodynamics, which was... really not my strongest subject."

- ThadisJones

Yo Eli!

hot guy GIF Giphy

"He took off his shirt at outback until the waitress asked him to put it back on then stood in the parking lot loudly (and badly) rapping to his own music. Shoutout to Eli."

- randomredittor21


"A woman asked me on a date to a dog park bar. I told her my dogs don't travel well so it would just be me, which she said was fine. I got there and she also didn't bring her dog. Then she tells me she's a recovering alcoholic and doesn't drink. So we're at a dog park bar with no dogs and no drinking. The date lasted another twenty minutes or so before she began crying about how she'd ruined everything and ran to her car. Suddenly I was a guy at a dog bar with no dogs or drinks that just made a woman cry and run away."

- SaddestClown

George Costanza

george costanza work GIF Giphy

"My George Costanza moment. Went out on a date with a girl going to college at a neighboring town. Went to dinner and what have you. When I went to take her back to her college apartment, we sat and chatted in my truck for a few minutes. Then she said "my roommates gone, do you want to come up for coffee?" My response was "no, I don't like coffee."

"She gave me a strange look, we said our goodbyes and I left. I was half way home when it hit me. I wish I could say I'm just going off the Seinfeld episode, but nope. tmobley87 is a big idiot when it comes to women. But met my now wife of 8 years the next month so I say it worked out."

- tmobley87


"I was 13 and it was my first date. She wanted to meet at some place and then go somewhere else, but I was pretty bad at knowing places so I had to ask my mom where it was. She gave me a lift and I thought she'd go away but she apparently went out to see what's happening. Not knowing I was being watched I met her and we started walking when suddenly my mom yelled out from behind us that we were going in the wrong direction. I was so embarrassed I wasn't able to talk to the girl normally after and just went home very quickly because I thought the whole thing was already screwed."

- _Norman_Bates


"When I was in high school I dated a guy with IBS and my parents insisted multipe times on having him over for dinners where he would just sit there because he couldn't eat any of our food. It would've been fine if my parents ever let him and I cook (food he could eat, which we always offered) or if people in my family freaking talked! We're a VERY introverted family and that's fine when it's just us, but when you're 17 and your boyfriend is bored and hungry and your family is just chewing in silence... ugh, the cringe."

- Waste_Barnacle4324

Excuse me?

Parks And Recreation Nbc GIF by HULU Giphy

"We went to Burger King, she asked me to take her virginity in the bathroom and I said no. This was followed by very silent chicken burger eating."

- -IIll

Fun and Games

"I invited my bf at the time over to watch movies in my basement. Instead my grandmother sat in between us and we watched the game show channel. For 3 hours. And it wasn't even like she was trying to prevent us from doing stuff. She just wanted to hang out with us."

- serious_rbf

When at Starbucks

"When I was a teenager, there was this girl that I really liked. We started to hang out a lot more after we ended up in a class together. Around two months after the class started, she asks if I want to go get coffee sometime. I of course say yes, ecstatic that she asked me out. However, while we were on the "date," she started saying stuff about how people always mistook her for a lesbian, saying how there is no way in hell she would ever go out with a girl."

"I was thrown off by this, because I thought that she, a girl, asked me, a girl, out on a date. I said that I thought that she asked me out, and she got really embarrassed, so now both of us are sitting in the middle of Starbucks on a sort-of date that only one of us wanted to be on."

- Catnip_cryptidd

Hold Please...

"We had a mediocre date, then walked to her apartment. On the way, she took a phone call about a couch she was buying. This call continues for the next few hours (!!!) of the date. To entertain me she put on a show on Netflix- You. This show is about a stalker, and is not really good first date material. At the end she said, resigned, "There isn't going to be a second date, is there?" And I agreed there would not be."

- Love-that-dog


Mel Brooks Poop GIF Giphy

"Was just a meet and greet coffee date with somebody I met online. We went for a walk down a tree lined street and a bird shat on my head."

- Jogaila2

Somebody find Eli. Now that had to be fun, at the very least. I just drag dates to karaoke. But, a parking lot works. And just so y'all know... I'm even MORE over dating now. LOLOLOL

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