People Share Most Embarrassing Date Stories

Reddit user u/ConneryFTW:

During my second year of college, I pulled an all-nighter while talking with a cute girl I knew. Talking with her felt good. I had been single for two months, recovering from a breakup. When morning came and our papers were done, she asked me out for breakfast to celebrate.

I looked like I just finished an all-nighter. She looked radiant; she clearly worked harder on this meeting. While we ate and talked, I felt great. I told her that. She smiled, looked shy, and asked if I was over my ex. I smiled back, said I was, and told her I was already thinking of the next person I wanted to ask out. She smiled wider and asked if I knew who it was, touching my hand...

I smiled and said, "I don't think so; her name is Rebecca, and she was in one of my history classes." Clearly, this was not the girl I was having breakfast with.

The girl I was with looked completely broken. I had no idea why. I think I said something like, "I'm sad the semester is ending soon, but I'll see you in the spring!" That ended what I later learned was the first date with the woman who became my wife.

Reddit user u/The_sad_zebrareplied:

Bro fumbled the ball. Then, he recovered it for a touchdown.

From Reddit user u/SaddestClown:

A woman asked me out for a date at a dog park bar. I told her my dogs don't travel well, so it would just be me, which she accepted. I arrived, and she didn't bring her dog either. Then she told me she doesn't drink. So we were at a dog park bar with no dogs and no alcohol. The date lasted about twenty minutes before she started crying, claiming she ruined everything, and ran to her car. Suddenly, I was a guy at a dog bar with no dogs or drinks that made a woman cry and flee.

Reddit user u/MZlurkerreplied:

That sounds awful, but I keep laughing at this.

From Reddit user u/Alarmed_Ste:

At a house party, the girl whose house it was pulled me into her parents' bedroom. We kissed and fumbled on her parents' bed. For some reason, I said something like, "Do you think your dad does this with your mom here?"

The mood died fast after that. I still cringe thinking about it.

If you read this, I'm sorry Kathryn. It was, and still is, the most embarrassing moment of my life.

Reddit user u/ChaseTheAce33replied:

I know for a fact you replay that moment in your head at 3 a.m.

From Reddit user u/serious_rbf:

I invited my boyfriend to watch movies in my basement. Instead, my grandmother sat between us. We watched the game show channel for three hours.

She did not try to stop us from doing anything. She just wanted to spend time with us.

Reddit user u/swordmalicereplied:

Your grandmother knewexactlyShe did not need to sit directly between you if she just wanted to hang out.directlyshe just wanted to hang out between you.

Reddit user u/Winterhe4rtreplied:

Lol... she knew.

From Reddit user u/cittegirl:

This was my first date with my now husband. We both felt very anxious about dating and had little dating experience. I threw up right before the date. He picked me up, and we drove to the library. We planned to use the WiFi to watch Netflix in the back of the car (even though I was almost 20, my mom would not let us stay in my bedroom at home). As soon as we reached the library, he got out of the car and threw up in the parking lot. I told him I had also thrown up before the date. He tried to claim we had the flu or food poisoning, but we both knew it was just nerves.

Reddit user u/Quokkamolereplied:

This is the cutest story involving vomit I have ever heard.

From Reddit user u/randomredittor21:

He took off his shirt at Outback until the waitress told him to put it back on. Then he stood in the parking lot, loudly and badly rapping his own music. Shout-out to Eli.

Reddit user u/Notthesharkfromjawsreplied:

For my last wish genie, I want to unread this comment.

Reddit user u/Express-Marionberryreplied:

For my last wish, I want Eli’s mixtape.

From Reddit user u/_Norman_Bates:

I was 13 and it was my first date. She wanted to meet somewhere and then go somewhere else, but I was bad at knowing places, so I asked my mom where it was. She gave me a ride, and I thought she would go home, but she followed us to see what happened. Not knowing I was being watched, I met her. We started walking, but suddenly my mom yelled from behind us that we were going the wrong way. I felt so embarrassed I could not talk to the girl normally afterward and just went home fast.

Reddit user u/KieDaPiereplied:

Sometimes adults forget how much every small thing means to a kid. I can picture how hard it must have been to shake off that embarrassment in the moment.

From Reddit user u/stephenstephen7:

I had a first date with a girl, and it was going well. We met the day before, we were connecting, and I felt confident and optimistic. We sat near the front of the bar, in sight of most of the people at a small round table. Then she asked if I could pass the water. Feeling tipsy and cocky, I decided to make it funny by holding the jug over her head, pretending to drop it on her. My hand slipped, and I actually poured the whole jug of water on her head in front of the whole bar. I think she knew it was an accident, but the damage was done, and several tables laughed at us.

That was the last time I saw her.

Reddit user u/Purple_Kreplied:

I do not know what went through your head that made you think it was a good idea.

From Reddit user u/Lil_Sousa:

A girl and I planned an outdoor mall movie. Middle school plans meant my mom drove me an hour through traffic. She canceled fifteen minutes before. I felt bad for my mom driving all that way. So, I acted like she hadn't canceled. My mom dropped me off. I watched the movie alone. I almost cried, but I held it in.

The movie was good, though.

Reddit user u/oPozzireplied:

I had a similar time. Instead of a movie, we went to a huge library. We both said we liked reading. We read a random book the whole time until mom picked me up.

From Reddit user u/Jogaila2:

It was just a coffee date with someone I met online. We walked down a tree-lined street. A bird dropped something on my head.

Reddit user u/hobbitdude13replied:

Life is a sitcom about you and us. We are all just living in it.

Reddit user u/FluffySloth27replied:

She bowed to Karl, the Chosen One, King of Ducks, Prince of Pigeons.

From Reddit user u/tmobley87:

My George Costanza moment. I dated a girl going to college nearby. We had dinner. Then, driving her to her apartment, we talked in my truck. She said, “My roommate left; want coffee?” I replied, “No, I don't like coffee.” She gave me a weird look. We said goodbye, and I left. I realized it was a mistake halfway home. But I met my wife of eight years the next month; it worked out.

Reddit user u/yersinia_pretzelsreplied:

Mine was this: Her: "Want a drink?" Me: "Sorry, I'm too cheap for a bar right now." Her: "It'll be my treat." Me: "No, really, that's fine."

It took me a whole week to figure out what happened there.

From Reddit user u/RosiePugmire:

It was one of those setups where my mom and his mom were friends. They said, "Our two nerdy, introverted loner kids should date!" Unfortunately, that was all we had in common.

Bonus detail: we went to a theater showingThe Big Sleep. He fell asleep.

Reddit user u/sil3ntsir3nreplied:

I had the same experience. Her mom, my mom. Two introverted, lonely kids. We went to the theater to watchKnives Out. I had to pee eight times while watching. She told me the whole plot.

From Reddit user u/critical_fail1:

I thought ice skating would be cute for a first date, even though I couldn't skate. I did not know she was a competitive figure skater. She literally skated circles around me. I knew it was over when she asked if she could do a few laps without me; my slow pace was too much.

Reddit user u/wunderbarneyreplied:

She was trolling you. She was silently giggling the whole way there. I guarantee it.

Reddit user u/callofslothreplied:

I took a girl out for a first date on an ice skating rink before Christmas. I had no experience; I had no business being there. I left in an ambulance with a broken tibia and unemployment.

Reddit user u/therapy_works:

During my freshman year of college, I went on a first date with a guy from my Italian class. We ate pizza. After dinner, we walked, and it started to drizzle. I wore ballerina flats with no treads.

I stepped on wet cobblestones. My foot shot out from under me. I landed hard on my butt. I felt mortified. I stood up fast. My date asked if I was okay. I said I felt queasy. Then I woke up in the gutter.

A woman stopped to help me. I got up and finished my date at the student health center. I broke my tailbone. I had to sit on a donut cushion in class for two weeks.

It did not work out. It is too bad. Breaking my butt on our first date would have made a great "how we met" story.

Reddit user u/PeacefulCouchreplied:

I expected a scene where he catches you.

From Reddit user u/gh0stmanX:

This was embarrassing at the time, but it worked out.

It was a second date, and it was Valentine's Day. I got her flowers, a card with music, and chocolates. It was freezing. I had nowhere to keep them except my car. I hoped the flowers might die.

We had a nice date. I got the flowers out when we got back to my car. Those flowers were DEAD. She said, "Ah well...". She opened the card, and the sound chip played, "bbbzzzzzzzz." I sighed and said, "Well... I hope the chocolates are okay." She laughed and gave me our first kiss.

Reddit user u/DekeKneePullsreplied:

Your heart was in the right place, bro.

From Reddit user u/ThadisJones:

I went with a girl to a late-night theater show. It ended around 2 a.m., long after public transit stopped. We had no car or money for a taxi, so we walked back to her family's house since I lived farther away. We fell clothed on her bed and instantly fell asleep. Three hours later, her dad woke me up. He asked who I was. When he learned I studied chemistry in college, he started asking me about thermodynamics, which was... not my strongest subject.

Reddit user u/Boston_Bruins37replied:

Her dad? Albert Einstein.