20 Dates That Quickly Went From Bad to an Absolute Catastrophe

When you’re on a date, the goal is usually to make a great impression and keep things smooth. But every now and then, things take an awkward turn, and what could have been a perfect night becomes a disaster. We gathered 20 stories where people revealed their most cringe-worthy dating moments.

• He insisted on picking the movie for our first date as a surprise. I told him, “No horror movies—I can’t handle them!” So imagine my frustration when the lights dimmed, and it was a horror flick. Five minutes in, I couldn’t take it anymore. I excused myself to the bathroom, fully planning to leave. I changed my mind when I got a message from an unknown number saying, “Are you on a date with Ethan? I’m his girlfriend.” I stormed back into the theater and confronted him right there. He froze, then muttered, “I was going to break up with her… eventually.” I immediately left.
• On our first date, we went to a classy restaurant. As soon as we sat down, she smiled at the waiter and asked, “What’s the most expensive dish on your menu?” My heart sank. I was ready to pay for dinner, but I hadn’t planned for a meal that would leave me broke.
  The waiter froze, glanced at me, and said, “I’m sorry, but that’s unavailable tonight.” She looked annoyed and tried asking about another expensive item, but again, it was “out of stock.” I gave him a very generous tip.
• I went on a first date with a guy who claimed he was a foodie. He insisted on picking the restaurant and ordering for both of us, saying, “Trust me, you’re going to love this place.” I was a bit skeptical, but I decided to go along with it. When the food arrived, I took one bite and felt my throat tighten.
  Panicked, I told him I was allergic to shellfish. He just stared at me and said, “Oh, I didn’t think you were serious about that.” I had to leave immediately to get treatment, and instead of being concerned, he stayed behind to finish his meal.

• My wife went on a blind date a few years before we met. On the phone, the guy said he would be wearing blue jeans and a T-shirt. My wife arrived at the venue and started waiting, but he wasn't there.
  After 40 minutes, when she was about to leave, a guy in sweatpants and a t-shirt came up to her smiling and asked, "Are you waiting for me?" She said, "Why aren't you wearing the clothes you described on the phone? I saw you, but I didn't know it was you." And he shrugged and replied, "My mum hasn't washed them yet." © kor_hookmaster / Reddit
• 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 Wi-Fi to watch Netflix in the back of the car.
  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 just the nerves. © cittegirl / Reddit
• My brother was downtown on a date with a girl when he learned he was lactose intolerant. They shared ice cream, a beautiful time. They were walking down the main street when the urge came. He freaked out and ran in the opposite direction. Went behind some bush, and exercised the demons.
  Turns out it was in front of an apt building with balconies. Some lads saw him while partying on the said balcony and screamed, "Hey, look! That guy's taking a poop!" Needless to say, he didn't get a second date. © neobuildsdashboards / Reddit

• I thought it’d be cute to try ice skating as a first date, despite not knowing how to skate. I was unaware she was a competitive figure skater and skated circles around me. I knew it wasn’t going anywhere when she asked if she could do a couple of laps without me, my beginner's pace was too slow. © critical_fail1 / Reddit
• 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 went out to see what was 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 / Reddit
• It was a second 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 got 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 / Reddit

• I went with a girl to see a late-night theater show. It ended at like 2 a.m., 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.
  3 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... not my strongest subject. © ThadisJones / Reddit
• 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 / Reddit
• I had never met this guy in person before, but we had developed a good rapport over the previous weeks over the phone and email, so I agreed to go out with him. We ended up meeting at a chain restaurant later, and I knew as soon as I saw him that I was in for an awkward time. He was dressed head to toe in Scooby-Doo gear, hat included.
  We greeted each other, and everything seemed okay, but the minute we sat at our table, he started talking about Scooby-Doo. Asked me what my favorite episode was, my favorite character, with whom I identify the most, have I ever thought about dressing like one of them, and so on. He did not talk about anything else, even when I changed the subject.
  We got our food, and I immediately asked for a box, telling him I needed to get home. He went quiet, and I could tell he knew that that was that. We split the bill and as I walked out to my vehicle, he said, "We're not going out again, are we?" © Wifevealant / Reddit

• Went out on a date with a girl going to college in 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 roommate's 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 halfway home when it hit me. © tmobley87 / Reddit
• I invited my boyfriend 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 / Reddit
• On my first date with this girl, we went to a restaurant called "Duck Duck Goose" which promised duck and goose dishes. We ordered duck meatballs and duck poutine. The duck meatballs had a sauce with it which just ended up being duck grease. The poutine curds were also made of duck grease and disgusting. After eating just one of the three meatballs, she confided in me that she hates ducks. And I realized that I hated ducks too. Anyway, then we got married. Every time we talk about going somewhere new, I'm always reminded that I make terrible decisions. © garlicroastedpotato / Reddit

• When I first started dating my boyfriend, I was very shy and inexperienced. I had extreme anxiety and aversion to the possibility of intimacy, to the point I would be physically sick to my stomach when I was around him.
  On one date we went to Texas Roadhouse. I ate a full meal, even though I was feeling the sensation of nausea and anxiety creep up on me. I could barely keep my food down when we left the restaurant. As we walked to his car, I puked all over the ground and on his sweater in the parking lot. © magic_is_might / Reddit
• My best friend was set to meet up with a guy from Tinder. He was running late, so she texted him, “Can I order us a pizza so it’ll be ready?” And he said yes. She ordered and paid for it, and when he got there they ate.
  The date wasn’t perfect, but fine. After the meal, he went to pay, but she told him she already had and he lost his mind! He went off on her on how she should have told him because he wouldn’t have eaten the food if he knew a woman had paid for it. © Waste_Barnacle4324 / Reddit
• I was 12 years old when I had my first date, it was late 1980, long before cell phones were a thing. The girl had shown interest in me and I thought she had cool taste in music so I was up for it. I took the bus to the military base she lived in (this was an air force base in Germany). I was walking to her house with plenty of time when I realized that I did not remember her exact apartment number. All of the buildings look the same. I said hello to a lot of strange people that night after knocking on their door. By the time I found her, I was late. We went to a dance where the boys I knew made terrible fun of me for having a date, something I did not react to well back then. Her friends were also being completely terrible. The night ended with her crying and me wanting to crawl into a hole and cover myself in the dirt forever. © imk / Reddit

• There was a girl that I had met through mutual friends, and we had a lovely dinner at an outdoor cafe. Then we went to my place for the first time and started kissing on my bed, which is when I felt something warm start to drip from my nose. It started bleeding and was dripping on her upper lip before I could catch it.
  I was horrified, and tried to wipe it off (which just smeared it), then ran to the bathroom to stuff a tissue in my nostril and get her a washcloth. She was as polite as she could be but promptly informed me that she was leaving and wouldn’t let me walk her to her car. © T412E / Reddit
• I was on a first date with a girl, and it was going well. We'd only met the day before, but we were vibing, and I was pretty confident and optimistic. We were sitting near the front of the bar and in an eyeshot of basically everyone there at a small circular table.
  Then she asked if I could pass the water. I, feeling kind of tipsy and cocky, decided it would be funny to hold it over her head, trying to be funny pretending to drop it on her head. And then my hand slipped, and I did pour the whole jug of water on her head. In front of the whole bar.
  Pretty sure she understood it was an accident, but by that point the damage was done, and there were several tables of people laughing at us. Needless to say, that was the last time I saw her. © Stephenstephen7/ Reddit

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