10+ Real Date Stories That Prove Love at First Sight Isn’t Always Beautiful

From painfully awkward silences to jaw-dropping twists, these awful first dates are packed with cringe and unexpected drama. If you’re into real-life dating disasters, messy relationship moments, and laugh-out-loud date stories, get ready to explore some of the worst first-date experiences that truly earn a drama award.

1.

• A few years ago, I went out on a date with a guy I met online. We went to a nice restaurant, and he ordered the drinks while I chose the appetizers. My drink tasted a bit off, and shortly after that I started feeling really dizzy. I went to the bathroom to get some air and ended up collapsing in the hallway. He didn’t even realize I was gone. The staff called an ambulance, and I was taken to the hospital with food poisoning. He only found out what happened when he texted me days later to accuse me of ghosting him.

2.

• I matched with a guy who wouldn’t stop talking about how “special” our first date would be. We met at a cozy restaurant, and halfway through the meal, he asked the waiter to bring out a cake. I assumed it was just a cute gesture, until I saw “Happy Birthday, Mom!” written on it and watched his mother walk in with two aunts behind her. He cheerfully introduced me as “the girl I might marry one day,” on our very first date, while his family grilled me about kids, religion, and my cooking skills. I blew out the candles, excused myself to “take a call,” and never went back inside.

3.

• I went on one date with a girl via the dating apps. We got dinner, and it was going well until she asked to see my work email. She said that she loved to see her friends and families work emails as it provides valuable insight on their lives. I was working for a judge at the time and everything was strictly confidential so I told her “no”. She got in a big tiff about it saying that it was no big deal, and everyone she’s asked has done it, and kept asserting that I show her my emails. I quickly paid for dinner and we left shortly thereafter. © mende2032 / Reddit

4.

• Went out on a date with a girl. Went pretty OK. A few days later, she texts me saying she is planning on taking a high paying job in New York.
  Having only gone on a single date, I said she should definitely take it and I wish her luck. She responds by politely asking me to never text again. Found out from a friend that she didn’t actually move. Apparently, she does this all the time. © BW_Bird / Reddit

5.

• A few years ago, this guy had a massive crush on me. He was nice enough, but I was dealing with a very early fall out of a long-term relationship. I wasn’t trying to date at all. One day, he showed up to the apartment I was staying at I didn’t want to see him because I was dealing with a lot, trying to sleep.
  But my roommate answered the door Let him in and let him come into my room, sit on my bed, kiss my cheek, and stare at me for like 5 minutes. Obviously, I wasn’t asleep, I felt paralyzed and couldn’t believe my roommate just let some guy into my room while I wasn’t responsive. After he left my room, I got up to chew out my roommate and there was a bouquet of roses in the kitchen. The whole thing felt creepy. I later found out he obsessively posted about me in group chats, saying some horrible things. © thatsruffpup / Reddit

6.

• First Date with a woman about 7-8 years older than me. Convo was going fine at Applebee’s but then she asked me if wanted to go half on a baby. Then she told me her clock is ticking and she wants a kid with me. Needless to say that was the only date. © DatboyTeedy / Reddit

7.

• “I was talking to a girl I met at a convention. We decided to meet up for a date. Showed up and it wasn’t the girl I’d given my number to. That girl gave my number to her friend and I’d been talking to this other girl. I don’t know if you’d call it ‘catfishing’ but it certainly freaked me out. I stayed and ate dinner with her then left and blocked her number.” © StoleUrGf / Reddit

8.

• Talked about her brother being her soulmate. And if he wasn’t her brother, her life would be great. Then showed me a picture. Looked enough like me to get me to say I needed to use the restroom and block her number. © Fonixx / Reddit

9.

• I was 31 years old at the time when I met a 28 year old guy online. He asked me out for lunch. During the date, he tells me that he lives in a 55+ senior living center. I asked him how he was able to live there and he said that it’s illegal for them to discriminate by age. It was so weird.
  © runnergal78 / Reddit

10.

• She cancelled before our first date, said there’s no connection, but we talked some more and agreed to go out again and hang out at her place to do a pizza and chill. I show up at her place after driving for 45 minutes, we talk for 10 minutes about her dog and she says “I’m tired” then went into her room and closed the door. Ghosted me the next day.
  © No_Bodybuilder9539 / Reddit

11.

• I travel often to Boston (about a 2 hour drive), so while I was in the area I matched with this girl and we hit it off. Unfortunately our schedules didn’t match up and I didn’t have a chance to meet her, but we made plans to go to a concert together in Boston the following week.
  We spent the week texting, calling, Face Timing, I had a hotel booked and a place to meet up, and I texted her as I was leaving my place to go up to Boston. She says “Okay! I can’t wait to see you!” And then I’m on my way.
  After about 3 hours of driving (due to traffic) I get to the venue a little early and text her that I’m there and wait to go in. No response for 30 minutes, I assume she’s on her way. I get inside, grab a drink and just relax, and that’s when I text her again. She responds, telling me she’s been inside and actually had a good spot on the floor and asked me to head over. I get there and she’s with a guy, and starts apologizing immediately.
  Apparently within the 3 hours it took to drive to Boston, she matched with another guy on Tinder who was also going to the concert, and decided that they were going to go together instead, but “I could hang out with them during the concert if I wanted to”.
  I politely declined, she tried reaching back out later the next day asking if I still wanted to meet up, but I just didn’t have it in me. The concert was fantastic though!" © *****-Engineer / Reddit

12.

• I went out with a girl who insisted we meet at her apartment before heading to a movie. When I got there, she introduced me to her roommate, who immediately sat us down and pulled out a notebook. She explained that she liked to “evaluate” all of my date’s potential partners with a list of questions about income, emotional availability, and long-term goals. Every time I answered, she scribbled something and whispered in my date’s ear like a talent show judge. After twenty minutes of this bizarre interrogation, the roommate said, “Yeah, I don’t think he’s the one,” and my date just shrugged and said, “Sorry, she’s usually right,” then showed me the door.

13.

• He picked a coffee shop for our first date and showed up in a full suit, even though it was 34°C outside. Before I could finish my latte, he pulled out a tiny portable microphone, clipped it to his lapel, and announced that he was “practicing for his future as a world-famous motivational speaker.” For the next 40 minutes, he paced around our table giving a loud speech about “crushing your goals” and “dating like a CEO,” occasionally pointing at me as his “live example.” People stared, one guy filmed us, and when the barista asked him to quiet down, he handed her a business card and said, “You’ll want this when I’m famous.” I quietly gathered my things, left him mid-speech, and later saw myself in the background of his “inspirational” TikTok.

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