10 Guys Confess the Cringiest Ways They’ve Screwed up a Date

1. “I hit her brother with my car. It wasn’t hard. He was fine. I want to get that part out of the way. I was dropping her off after a date that, up until that point, had gone pretty well. I pulled into her driveway and while I was still coming to a stop, I turned to look at her. I thought I was being all smooth and started to say, ‘so…’ and was setting things up for a goodnight kiss. I didn’t realize her brother was crossing the driveway. She yelled at me to look. He assumed I saw him and was stopping in the driveway and I just sort of tapped him. He rolled up onto the hood, more out of instinct that anything else, he said. But for a second I thought I was going to jail. I don’t know why. Like I said, he was fine and miraculously we actually dated for a while after that and it was just something to laugh about.” — Rich, 29

2. “I was almost 12 hours late to a first date once. We were discussing meeting up on a Saturday on Tinder; she suggested dinner, but I said I couldn’t. I had a whole bunch of stuff to do so [I had to go into work that day]. I said, ‘I can’t do that, but I can do 11 instead.’ I know that was late, but I was thinking of it as more of a casual drink thing. I didn’t want to tell her 9 and be late if I had to work longer. So I propose that assuming it’s 11 PM, and that if that’s too late we can just reschedule. She agrees to it, but she thought I meant 11 AM. Which, I guess since I had said I had to ‘swing by the office to take care of some paperwork’ is understandable. Anyway, I’m busy at work, blissfully not paying attention to my phone. Around 3 PM I see all these messages from her like, “where are you” and “???”. I apologize profusely, manage to get out at a semi-reasonable time and basically beg her to let me buy her a dinner to make up for it. She was pissed at this point, but for some reason still decides to meet up with me and was giving me the cold shoulder the whole time. It didn’t go well, but it was really just a misunderstanding.” — Michael, 28

3. “I was once late for a date because I got stuck at work, and then spent most of the date ranting about my job. My date didn’t even order anything. I got a beer and a burger because I was starving and she just politely listened to me vent. She was nice about it, but there was no way I left a good first impression.” — Brett, 28

4. “I got… and I don’t know how this happened… but I got wasted. I wasn’t trying to. I didn’t really eat much that day and it just hit me hard before I realized what was going on. Her friend had to pick her up and drive her home.” — Steve, 27

5. “Not that this makes me a horrible person, but I took her to a seafood restaurant and she was allergic to seafood. It was a nice enough place and she laughed it off, but it slowly dawned on her that there really wasn’t much on the menu she could order. We wound up going somewhere else.” — Ethan, 27

6. “We went for a hike in the woods. It was my idea and I got us lost. It wasn’t like, ‘the park rangers deployed a search team’ lost. But we wound up in the woods for 2 hours longer than we had planned. She also wasn’t a very experienced hiker (not that I was either, obviously), but she wasn’t looking to do any extra hiking. Needless to say, she never answered any of my calls or messages after that.” — Derrick, 27

7. “I guess ‘date’ is sort of a stretch here, but I made plans with a girl on Tinder and we were just going to hang out, really. She was really excited because she had just gotten this new bong that was really high-end and custom made by this small shop… I won’t bore you with details but it was pretty expensive. Anyway, we’re smoking and she breaks it out and we’re talking and she’s showing me everything. And I fucking drop it, and it shatters. It really killed the vibe. I paid for a new one and everything, I’m not an asshole. But you know, the rest of the date she was really upset obviously.” — Jon, 28

8. “I took a girl to a restaurant I really liked and…. my parents were there, also. So she met my parents on the first date.” — Seth, 30

9. “I definitely inadvertently ruined this one date I went on. It was a blind date, and it was right after Mother’s Day. And I was telling her what my siblings and I had done for my mom on Mother’s Day. We had surprised her and gone for a weekend away to this little inn she had always wanted to go to. And there were a few funny stories that happened, and plus I figured it’d give me some good brownie points and impress my date, right? So I talked about it for a while and she starts crying. It turned out her mom had just passed away and I wound up taking her home. The silver lining here is that we’re actually still dating now and it’s going on two years, but at the time I felt awful. But I really blame my friend that set us up for not at least mentioning that to me.” — Matt, 29

10. “While deciding what to order, I went on a whole rant about how stupid and pointless I thought being vegetarian was. Guess who didn’t eat meat?— Jay, 27

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