15 People Whose Dates Didn’t Go Quite as Planned

Dating can be unpredictable, and sometimes, even the best intentions lead to awkward, unexpected, or downright bizarre moments. Whether it’s miscommunication, bad timing, or a twist of fate, many of us experienced those dates that didn’t quite go as planned. In this article, we share 15 stories of people whose dates took surprising turns, from awkward missteps to uncomfortable revelations.

• I was on a second date with a girl. I missed my last ride home, so she said I could stay the night. We stayed up talking until we passed out. Half asleep, I felt a hand on my shoulder.
  At first, I thought it was a nightmare, but when I opened my eyes, I saw her standing there, staring at me. She just said, “I can’t sleep. You’re snoring really loud.”
  Then, without another word, she grabbed a pillow and blanket and made up the couch. “I’m sleeping out here,” she said, smiling awkwardly. That was the last time we hung out.

• I met an attractive girl on Tinder for a late dinner. She seemed nice in her profile pic, but when we met, things got strange. She showed up with a couple of friends, and they all seemed really close.
  Turns out, they all go on each other’s first dates and decide collectively if it’s a good match or not. I was a bit taken aback when they explained this tradition, but I stayed out of curiosity. The night quickly turned into a group interview. I felt more like a contestant than a date.
  After a while, I noticed them evaluating me with subtle glances and gestures, which felt pretty unsettling. So, I decided it was time to bow out. I finished my meal, politely excused myself, and left. I blocked her after that night.

• [edited] So this is embarrassing in retrospect. In my second year of college, I pulled an all-nighter with a cute girl I was friends with. We were messaging throughout the night, and when we finished our papers at dawn, she asked me out for a celebratory breakfast. I showed up looking like a zombie, while she looked radiant and put more effort into this than I did.
  The sun was filling the restaurant with warm light as she coyly asked if I was over my ex. I nodded, feeling good about the moment, and mentioned that I was already thinking about the next person I’d like to ask out. Her smile widened, and she touched my hand, asking if she knew who it was.
  Without thinking, I replied, “Rebecca, from my history class.” Her face dropped, and I had no idea why—until much later, when I realized that was the first date with the woman who would later become my wife. © ConneryFTW / Reddit

• I’d liked her for months, so when she finally agreed to go out with me, I was excited. But every date felt off. She was always on her phone, constantly taking pictures for social media, insisting we post them together. I wasn’t ready for that, but I went along with it, thinking it was no big deal.
  But something didn’t sit right. Then I found out the truth—she was still seeing her ex, using me to make him jealous. I was young and heartbroken, but ultimately relieved to move on.
  Four months later, I met the love of my life. I married her last month, and I’ve never been happier.

• There was a girl whom I had met through mutual friends, and we drifted in and out of each other’s lives for a few years. I finally asked her out, and after a few dates, we had a lovely one at an outdoor café on a beautiful late summer evening.
  We went back 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. As she walked out the front door, she turned and told me, “It’s really too bad, because I was in a REALLY good mood tonight.” And she was gone.
  Somehow, we’ve been together almost 10 years and married for six. Love you, sweetheart. © T412E / 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 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 ruined. © _Norman_Bates / Reddit

• [edited] I met her in an adult soccer league and invited her to breakfast. She agreed, so I took her to a small diner. During the meal, she shared some very personal interests. That was more than I expected.
  Afterward, I realized I’d forgotten my wallet, so she kindly paid for both of us. She invited me back to her place, and I went, feeling like I owed her. Things escalated quickly, and about an hour later, she got a text and panicked, “You need to leave, my boyfriend’s coming home early!”
  This was the first I’d heard about a boyfriend, and I suddenly realized I’d just spent time in her boyfriend’s bed after she’d paid for our meal with money he gave her. In a rush to leave, I jumped in my car, knocked over a mailbox, and cracked my bumper. Now, she won’t stop texting me. © BEST_NARCISSIST / 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 literally 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 beginners pace was too slow. © critical_fail1 / Reddit

• [edited] 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 keep me entertained, she put on a show about a stalker, which 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 / Reddit

• 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 told me she didn’t want to get served. So, we’re at a dog park bar with no dogs, just sitting. 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 park bar with no dogs, no distractions, who had just made a woman cry and run away. © SaddestClown / Reddit

• Back in college, I was invited to an ice rink with a girl I liked and some of her friends. I did not know how to ice skate, and I did not pick it up very quickly, but I wanted to try and impress her somehow. Well, I hugged the wall the whole time and made a fool of myself.
  The highlight was when I saw a flash of light as I fell in front of a group of people. Turns out I had fallen right at the moment someone took a picture, so my failure was immortalized forever. She took me back to my apartment and ended the relationship before it began.
  On a lighter note, the woman who is now my wife was at that ice rink on that night. We didn’t realize we were there at the same time until a year or two into our relationship, and she exclaimed, “You were that guy who couldn’t ice skate! Yeah, she didn’t seem that into you.” © Krell47 / Reddit

• I’m not gonna say date, but this coworker and I eventually dated. We would go walking after work at this big park, and afterwards we’d go to a Stop N Go for bottled water.
  Well, it was a lottery night and the lot was full, so I had to park at least 10 or so parking spaces from the front doors. It’s a chilly fall evening, so I get out with the car windows closed. I get the water and come out of the store, and notice that she has both of the windows about halfway down.
  So I get in, and it smells really bad, like she had passed gas. She apologizes, but I just laugh really hard, and then she starts to laugh too. We hung out a lot as coworkers, but that incident made me have a talk with her to start dating, and we did. © r***31264 / Reddit

• Finally asked out a really gorgeous coworker, she said yes. Take her to a party and we rode with friends there. Once we’re there, she proceeds to get on her face, then spends the evening talking and flirting with another guy there that I didn’t know.
  Evening ends, and we ride with friends back to our vehicles, dude comes along too and they both make out with each other next to me in the back seat. My only revenge is that I told everyone at work how the date went. © polyesterbrown / Reddit

• [edited] I went on a first date with a girl I met through community theater. We went to see Cloudy With a Chance of Meatballs, but quickly realized we had too many conflicting interests, leading to uncomfortable discussions about some tense topics. I texted a friend to vent about how poorly the date was going.
  Just after I hit “send,” my date’s phone chimed. She pulled it out, read the message, and asked, “Did you MEAN to send that to me?” I realized I’d accidentally texted her instead of my friend. She was upset, but we finished the date as friends, awkwardly.
  Later that night, I texted my friend again about the disaster, and my phone chimed: “You sent it to me again.” © Rocktopus_PhD / Reddit

• [edited] I went on a first date with a girl who seemed great—good-looking, funny, shared similar interests. We were chatting at a bar when the conversation turned to the usual first-date questions. I asked, “So, you work in an office, but is that what you really want to do?”
  She reaches into her bag and pulls out a red clown nose, putting it on. “I’m actually going to clown school,” she says. I was shocked—it was our first date!
  Trying to recover, I joked, “So, are you in clown university or clown college?” She took offense, and for a clown, she had a terrible sense of humor. © AlfieTorp*** / Reddit

Not every date is destined to be a fairytale. But these stories remind us that sometimes, the most memorable experiences are the ones that don’t go according to plan. Whether you’re laughing at the mishaps or cringing at the awkwardness, there’s always something to learn from these unforgettable moments. For more dating tales that didn’t go as expected, check this article.