15 Dating Stories That Begin Innocently but Turn Into Chaos

Dating can be exciting, romantic... or a gateway to pure chaos. Everything starts well: an interesting conversation, a coffee that doesn’t spill (yet), a feeling that this time it might work. But suddenly something changes.

Maybe the person you’re having dinner with decides to tell you all about their parking tickets. Or you realize that the “surprise dinner” is actually a family reunion where you’ll be introduced as their future spouse. Or worse, the date ends in a police chase (yes, there are stories like that).

In this article, we have compiled the strangest, most disastrous and downright bizarre experiences that internet users have shared about their worst dates. Get ready to laugh, be surprised, and most of all, be thankful that it wasn’t you who went through this.

• Last year, I decided to text a cute girl I had class with last semester to ask her out, and she said something like, “Sure! I was hoping to hear from you again!” She said she was a good bowler, so we arranged to go bowling, and the date came up the next week.
  She was sitting on the railing outside the bowling alley waiting, and when I got out of the car and smiled at her, the girl said, “Oh, hey! I didn’t expect to see you here!” That confused me. I thought something might be up, but I couldn’t think of a good answer, so I pretended I wasn’t expecting to see her either.
  I asked her if I should go inside and get a lane set up for us and she said, she frowned and added “Yeah sure, just wait a minute... I asked another friend to meet me here.” When I asked who it was, she told me it was her friend who happened to have the same first name as me. I went in and handed over some free game passes, put on my shoes, and then put our 3 names in the machine.
  I didn’t want to just start without her, so after about 10 minutes of waiting, I got a text from her saying, “Where are you? I really don’t want to be stuck here with this guy I used to have class with!” So I found out that my instincts were right, but as a bowler with free bowling passes that were about to expire, I wasn’t about to just leave. I replied, “Sorry, family emergency, I can’t make it,” and a minute later she came back in and found me at the lane I was on.
  When I asked her about her boyfriend, she told me he wasn’t coming. When I asked her if she was ready to start, she told me, “I’ll just watch, I don’t really like bowling, I just came to watch my other friend, he’s supposed to be a really good bowler.” So I said to her, “Well, if you’re not going to bowl, there’s no point in staying, I was just going to practice for a match anyway.” We said goodbye and I never heard from her again. © Jollies / Reddit
• Back when Tinder first came out, I matched and started talking to a girl who was in my same town. She and I agreed to meet at a restaurant I had been to a few times. We had talked about it being just the two of us, but when she arrived, she was dragging a kid with her that she had never mentioned having, let alone bringing.
  She sits down and almost immediately gets on her phone, largely ignoring me and her child. I tried to strike up a conversation, but it was clear that she was not there for me at all. So her kid and I started coloring on placemats, drawing cartoon characters and stuff like that. The food comes, we all eat, and then she asks if she can order another entrée.
  I had no intention of paying for her food at that point, so I said, “Sure.” I get up to “use the bathroom” and go to the waiter for the check. I pay for my food and the kids’ food because he and I were having a pretty good time drawing Minecraft characters. I stuck her with both her entrées and her drinks and then left, blocking her from everything. © Crude_n_tattooed / Reddit

• The date started well, decently. We were both a little nervous, but after a few minutes we became more confident. It was my first real date since my divorce, and she told me it was for her, too.
  So while we were swapping stories, I asked her about her ex. She smiled, said, “Oh, he’s right over there,” and pointed to a guy who returned our greeting.
  To my shock, it turned out they were still living together, and he was driving her around. He didn’t seem happy either. I got the hell out of there. © TheP***Shiver / Reddit
• On the fifth date, the woman admitted that she had two children. The shock was strong, but I let it go and told her I was still interested. However, she then admitted that she was still married. This shocked and disgusted me.
  I told her what she was doing was wrong, but her response was the final straw, “Can I leave him for you?” I felt sick and told her that she would probably do the same to me. Then I just walked away. © Unknown author / Reddit
• The summer after I graduated from high school, I went on a date with a girl I had been friends with for a while. We decided to go to a carnival a few towns over. We would walk around, eat some fried food, go on a ride or two. Things went great and a lot of laughs were had.
  Then we went on a ride similar to a Zipper/Salt and Pepper Shaker. Lots of spinning upside down and so on. About halfway through the ride, the funnel cake I had earlier decided it did not want to stay in my stomach. With her sitting next to me, I start throwing up... and then we flip upside down... and my vomit comes right back in my face.
  I had enough sense to keep most of it away from her as she came off the ride vomit free. I did not. We have been together for over 6 years now, are currently engaged, and will be married next summer. © Crashmaster007 / Reddit

• On one of my first dates, I took a girl I really liked from school to the movies. During the commercials I went to the bathroom and when I came back the movie had started. Since it was really dark, I sat back in what I thought was my seat.
  Turns out I was sitting two rows behind her next to another girl and a guy. I only realized it when the lights came on at the end. I guess I was too nervous to realize. © soundguy_2603 / Reddit
• My FIRST date, actually. With a friend of a friend, the summer after my junior year of high school. She suggested we go to a cute coffeehouse, I thought it would be perfect since we both love coffee. Plus, being brand new to dating, I JUMPED at the chance to plan a whole day together doing “mini-dates” since we really hit it off and had a ton of chemistry, it seemed, before I even asked her out.
  The coffeehouse she suggested was one where a former fling of hers worked. She acted all embarrassed, like she hadn’t picked the place on purpose. Being gullible, I thought it was an honest mistake and wanted to continue with our planned day. She was on her phone for a good part of the day, but I chose to ignore it. I guess I realized it was a red flag, but I was so excited to be on my first date that I didn’t know to expect more.
  Next thing I remember, she asks me if I want anything else, I said no, I was just finishing my coffee, figured she was using that as an excuse to make a phone call or whatever, she’s on her phone a lot and all. Then I look up, and she’s talking to her ex-boyfriend, and they walk out together. I thought they were arguing(?) or something, so I give her a few minutes.
  I texted her something like “Got lost on the way?”.... no reply. Then a few minutes later I texted her “Are you ok?”... no reply. I paid for our coffees and left. Never heard from her again. © cocoabuttersamurai / Reddit

• I met a girl on an online dating site. She seemed pretty normal, so I took her out to dinner for our second date. After a good conversation about various topics, she casually said, “I don’t usually show this to people this early,” and then pulled out a book with all the pages torn out.
  I looked at her very quizzically and asked her what kind of book it was. I don’t remember exactly, but her answer sent shivers down my spine, “I eat paper and I eat this book.”
  I tried to interpret it as normally as possible and asked her questions about it. I even ended the date with a hug. Come to think of it, that wasn’t really the dealbreaker, but still... © Unknown author / Reddit
• A few months ago, I went on a coffee date with a girl and got there a little before her. When she arrived and saw me, I couldn’t help but notice a surprised/confused look on her face. I thought maybe she thought I looked different, but I don’t lie about my height and my pictures are pretty accurate/new, so I was unsure.
  The date ended up going pretty well, but I got a message pretty quickly after that she enjoyed the time but didn’t see it going anywhere. This almost had me overhauling my hinge pics because I thought it must have been me that looked different, but I ended up seeing a TikTok of hers later (TikTok occasionally shows you videos from people in your contacts.)
  The video had the caption “Dating fail” and was posted right after our date, so I had to check it out to see if it was about me. In fact, it was about me, and it turns out she got my number mixed up with someone else’s and thought she was going on a date with someone else. In the video she said I was nice/cute but not her type. The whole ordeal was funny to me, glad I wasn’t catfished. © jonrah** / Reddit
• The guy showed up half an hour late with a cast on his arm. He ordered a steak and asked me to cut it for him. The whole meal, he talked about himself and complained about his job. Afterwards, he asked me to walk him to his car, which was only a few blocks away.
  At the end of the date, he tried to kiss me and when I gave him the cheek, he called me selfish. The next day, he asked me out on a second date. I blocked him. © nguyenmh2 / Reddit

• He lied about knowing ASL and then acted offended when I pulled out my phone and asked him why he lied because there was no need. I was fine communicating by text. He said he lied because he didn’t think I would be able to tell.
  He stayed angry the rest of the date, wouldn’t make eye contact, and when I left he wanted me to apologize for humiliating him. He was the one who lied, so I just left. Before we even met in person, I told him I didn’t expect him to know ASL and that texting was fine, but he made a big deal about being able to sign. © wrappedinplastic315 / Reddit
• A few years ago, I dated a girl. From the beginning, talking to her was like talking to a brick wall. I would ask her a question and she would respond with a single word or a short phrase. She would never answer me or try to keep the conversation going.
  At one point, she went to the bathroom and an older woman sitting at the next table leaned over and whispered, “I have to say, I admire your patience. She is a nightmare.” Plow twist: that older woman became my wife. She did make an effort and interacted with the conversation. © Realistic-Whereas865 / Reddit

• At 24, I was working in a fast food restaurant and a guy came in with his mother. Later, he came in and asked me out for ice cream.
  I got all dressed up and looked cute. He showed up in sweatpants. He told me he didn’t want to ask me out because I didn’t look like I was going anywhere in life, but his mom told him to (he was 24 too). He then goes on about this board game he created in the style of League of Legends. He did not ask me any questions, did not engage with me, just talked about his board game.
  Then out of the blue he tells me that he has a girlfriend (excuse me?) but that she is so ugly. He explained that she was a 3 on a scale of 0-10, but I was a 5, so I was an upgrade! I had no idea I was that low on the rating scale at that point, and didn’t realize people even rated people out loud at our age. He then goes on about how his girlfriend didn’t have a job. Apparently, her parents gave her money because they were rich.
  I was way too nice to walk out on this date, so I literally gave him dating advice... on our date. Then at the end he said he had to go because he said he’d play video games with friends. He paid for the ice cream on the date, and he literally said, “Don’t worry about paying me back, I make a lot of money.” Then he left. © thriftybabygurl / Reddit
• A guy I met on a website asked me to go shopping with him. He seemed nice, and besides, he loved shopping just like me! But the first thing he said when we met was, “I’m obsessed with shopping.” I thought, “Great!” But no, it wasn’t.
  He and I spent over 2 hours at the mall, asking to go into every store and buying the most expensive item in EVERY store. At one point, he was humming about a pair of ski goggles that were full price, and we were in the middle of summer. He spent over half an hour looking at them, and I was bored out of my mind, and I NEVER get bored shopping.
  By the end of the day, he had about 20 bags that he had bought for himself, and I had maybe one or two items. I walked away from our second date. © Unknown author / Reddit
• I have a speech impediment where I cannot pronounce my "r“s clearly. 99% of the time, this is of very little consequence. But one time I was on a date with this girl in college, and she showed me some drawings she had done.
  I said to her, “Wow, you sure are artistic.” Well, apparently she thought I said, “Wow, you sure are autistic.” She got really mad and stormed out. I did not get a second date. © *****-Pit / Reddit

Dating can be a rollercoaster of emotions: sometimes it ends in eternal love, and sometimes it ends in an anecdote that your friends make you tell every time you get together. And if you liked these stories (or want to feel better about your own experiences), you can read this article where we explore more awkward, unforgettable and, in some cases, almost cinematic moments.