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.