12 Dating App Moments Men Still Can’t Believe Actually Happened

Dating apps were supposed to make finding love easier, but for many people, they’ve become a chaotic world full of surprises, secrets, and plot twists no one sees coming. Here, men share the most unexpected, bizarre, and mind-bending dating app experiences they’ve ever had — stories that prove meeting someone online is never as straightforward as it seems.

• I got catfished. She was heavily editing her photos using Facetune or something similar.
  During the date, we were talking, and she just pulled out her phone and started mindlessly scrolling through social media. At that point, I just stopped talking, and she said, “Yeah, yeah, you keep talking. I can hear you.”
  The worst part is that I went to another city to meet her. © momsdirtysecret / Reddit

• I matched with a girl who seemed genuinely sweet. Great chats, lots of laughing, everything felt easy. But the moment we met, she kept checking her reflection in every shiny surface — windows, spoons, even her phone’s black screen. Halfway through the date, she excused herself to “powder her nose.” She never came back. I texted, thinking maybe something happened. She replied an hour later: “Sorry, I saw someone I used to know and didn’t want things to get weird.” But then she admitted she didn’t actually see anyone. She just panicked because I “looked too confident in person.”

• We went to the biggest coffee place in Munich, Marienplatz. It was crowded as hell. She looked hot and all, but we talked for like 3 hours—it was all great—up until she went down on her knees, proposing to me... creepy? Everyone was staring at us.
  At first, they looked disappointed and angry at me for obviously saying no. She rushed out in tears. I had to explain to the 100+ people around me that IT WAS OUR FIRST DATE. © Cengiz96 / Reddit

• I am widowed and dating again. It’s difficult to use a dating app as I came from a time before when I did very well, and there were no apps. I met a woman, and we decided to meet at Starbucks in the Barnes & Noble bookstore, which is attached to a mall.
  The conversation was going well. We walked into the mall, and she bumped into her ex. They started arguing and started fist fighting. A crowd gathered, and security showed up. I ducked into the crowd and made a beeline to my car.
  She texted me later to apologize but commented on why I didn’t step in to defend her. I just said I wasn’t interested and blocked her. © nomaxxallowed / Reddit

• Every picture, every call, every date — same hoodie. I assumed it was her comfort clothing. She said it was “just her style.” One day, I accidentally spilled coffee on it. She panicked like I’d ruined her passport. When she came back from the bathroom, she finally told me the truth. Turned out she didn’t own just one hoodie. She owned twenty-three identical ones. She hated making outfit decisions, so she spent her first paycheck buying duplicates to wear every day. I’ve never met someone so committed to reducing stress — and so stylishly minimalist.

• I matched with a woman who was fairly local. Somehow, during one of our conversations, I mentioned my neighbors by name (I had recently bought my house and was in the process of moving in). We hadn’t met face to face yet, but it was becoming a possibility.
  One day, I was outside changing the lock on my front door when I noticed a car slowly driving by. It seemed odd, but I didn’t think much of it at the time.
  Later, I got a text from her. It was a picture of me with my back turned to the road while I was working on my front door. I didn’t date for a few years after that interaction. © Sh***yCommentor / Reddit

• I had a great first date with a girl from Tinder. She was super happy to set up a second date for later that week and was sending me memes and chatting until the night before. On the day of, she decided to stand me up in below-freezing weather without any warning. I was texting her, asking where she was, and I could see her come online just to ignore me. © Rambo7112 / Reddit

• I went on a date with a girl, but when I got there, her friend was also there. She told me it was because she wanted me to date her friend, but I told her no—that I had talked to her, and I came to have a date with her. I told her I was going to leave, so she asked me to stay. After a while of us actually talking, she decided she wanted me to date her and not her friend.
  I stayed and talked to both, then left and never talked to them again... so weird. © solar-jutsu / Reddit

• I matched with a girl who looked oddly familiar, but I couldn’t place her. She joked that I probably saw her “in my dreams.” Cute. We clicked instantly — banter, flirting, everything. Then during a call, she said something only one person on earth would know: the nickname my ex used to call me, one I never told anyone because it was embarrassing. My stomach dropped. Turns out, she was my ex’s cousin. My ex had told her “to talk to me and see if I was still an idiot.” Apparently, I passed the test — because she said I was “way more fun” than she expected.

• I matched with someone and agreed to go out after I got off work. She was an hour late, texting me updates like “running late... doing my hair... be there soon,” etc. Stuff happens, I can wait. Then she sent me a picture from outside the bar with my back turned, saying she was outside. I went to where the picture was taken, and she wasn’t there.
  I decided I was tired of being messed with and told her I was leaving. She seemed disappointed. I told her I’d be down to try again, but nothing ever happened. © ercdude / Reddit

• Agreed on a bowling date, and she asked if we could include friends. I said sure, but it would probably just be me on my end.
  I showed up at the bowling alley and waited for her out front. She arrived with four or so girlfriends. Okay, no problem—this should be fun.
  We all walked in, got our shoes, and ordered some drinks and a food package. The cashier said, “It’ll be three hundred and some change.” They all looked at me and said, “Thank you.”
  I said, “No.” (I would have covered her cost, but not after that.) I put my shoes back on the counter and left. © O**seBMI33 / Reddit

• I matched with a woman who only wanted to call late at night — never morning, never afternoon.
  She’d text all day, but video calls only happened after 9 PM, lights off, face half-hidden. Mysterious, but I liked it.After a month of this, I insisted on meeting. She panicked, then calmly said she’d explain in person. We met at a café, and she walked in looking exactly like her pictures. Except she wasn’t single.
  She confessed she downloaded the app because her boyfriend had installed strict parental controls on her phone, blocking social media. Dating apps were the only things not restricted. She’d been using me as her “escape window.”

These experiences remind us that in the world of online dating, nothing is ever exactly what it looks like. Whether these encounters left them wiser, wary, or weirdly grateful, one thing is certain: every swipe has the potential to become a plot twist of its own.