14 People Whose First Dates Turned Into a Catastrophe

3 months ago

We’ve all had our fair share of bad dates, but some people have experiences that are just next-level bizarre. Luckily, the internet gives them a safe space to talk about these unforgettable encounters, which range from awkward to downright creepy.

  • Great chats online, decided to meet in person.
    He’s got a Bluetooth headset with a little LED light that shows it’s on. He keeps it on during drinks. I work up the nerve to ask if he can take off the headset while we’re eating dinner.
    With pride and complete confidence, he says, «Don’t worry! You totally have my full attention. This isn’t a phone headset, it’s a camera© anarchypretzel / Reddit
  • We were at a restaurant and the waitress came over and gave the standard greeting, «Welcome to...can I start you off with some drinks?» I ordered a water and a drink and then looked at my date and said, «And whatever she is getting.» My date then looked at me, looked at the waitress, and looked back at me with a confused look on her face. So I asked if she was okay or if she needed more time to look.
    My date then cleared her throat and asked me if I knew the waitress. I said no and asked why. The date then went on a rant about why the waitress was talking to me and looking in my direction when she should only be talking to and looking at her. I was shocked and was like, «What?» She then goes on about how if the waitress and I have something going on, to just let her know now.
    At this point I looked at the waitress and told her to cancel my drink order, apologized to her, then I got up and left. When I got to my car, I blocked the date’s number and everything. © Capitolkid / Reddit
  • First date, we’re meeting at a new pizza place in town. She tells me to get out of my car first. She then sees me and laughs, going, «That’s your tiny car?»
    We’re in line to create our own pizza, we’re talking, mid-conversation she pulls out her phone and blocks me on Tinder and Snap visibly in front of me. I walked out in the middle of our dinner as she was asking me where I was going. © mattjwx / Reddit
  • I had a woman call me and insisted I give her my number one night when I was bartending at a small music venue during a concert. The name and description didn’t sound familiar, but we chatted for a few nights and decided to meet. I will call her Bonnie.
    We met up at a bar in her part of town. Bonnie looked a little familiar, but not someone I would have given my number to. She was not my type. But I decided to not be rude and gave the one date a chance. Somewhere in the course of the evening, we started sharing pics from our phones. «Here is my dog», «Here is my son», «Here is me in Vegas,» etc.
    Then Bonnie showed me a pic, «This is me and my best friend Sarah.» I looked and Sarah looked very familiar. Sarah WAS my type and I remember chatting it up with her and giving her my number. Then it occurred to me that Bonnie was the woman standing behind Sarah the whole time, just minding her own business the night I gave my number out at my place of work. Her best friend Sarah catfished me in person on behalf of her friend. I left. © t480 / Reddit
  • We agreed to have the first date at a restaurant. After 10 minutes, she tells me she wants me to pay for her food and also two separate take-out orders for her two best friends, because «that’s what a real man would do». I pretended like I was cool with it, then said that I needed to get my card from my car and left her there. © Unknown author / Reddit
  • Had a first date with a girl who insisted we go to a really expensive place, where she ordered a 25-dollar appetizer, a $45 steak, and a $15 drink. She wouldn’t put down her phone and kept taking calls and answering texts. The waitress noticed and motioned for me from behind her.
    I excused myself, and the waitress had separate bills all made up and asked if I wanted to pay my share and leave her at the table. I said, «That would be wonderful!» So I did. © ELPwork / Reddit
  • I had known this girl for like 2 years from college and had a huge crush on her, but we were best friends. I man out and asked her if she wanted to grab a coffee with me, as a date.
    We were talking, and she started telling me about all the guys she’s been with intimately, which I don’t care about since I also dated during that period, but I wouldn’t brag about it to her. Anyway, she started saying that if she started dating me I would probably be the ugliest guy she was ever with, and she would be embarrassed when sometimes people get the wrong idea about us.
    I almost started to cry. I loved this girl so much and that really hurt my pride, we were best friends, and she usually wasn’t like that. I told her my feelings and just left. © iamnotalways*** / Reddit
  • This happened to a friend. Context: he has a beard. So, my friend picks up this girl, and they’re on their way to dinner, and she says, «You do realize that if this is gonna work you have to shave that off right?» He didn’t say anything, just turned around and dropped her back off at her house. © Jeborisboi / Reddit
  • Went to meet a guy for the first time at his house. There was a pile of toenail clippings on his coffee table. And it wasn’t one recent clipping. It was like, many clippings. Out the door, I went. © Amos_Moses83 / Reddit
  • In college, I went on a date with a girl who rolled down her car window and threw an empty soda can out. I told her to drop me off at the next stoplight and walked home. © HerrowPries / Reddit
  • He invited me and a friend to play dodgeball with a group of folks I’d never met. We’re having an ok time, he’s paying more attention to his friends, but that’s fine because I’ve got my friend to keep me occupied. We’re hanging out in the parking lot before the first game is about to start when, out of nowhere, he grabs a ball and throws it at my crotch. This guy then screams, «Wham, bam, right in the clam!»
    I immediately turn to my friend and ask her if she’s ready to leave. I say goodbye to him and his friends. Immediately came home to a grip of texts about how «immature» I was behaving. © Monpetitvulcan616 / Reddit
  • We met outside of one of my favorite restaurants. She was texting on her phone, shook my hand, and barely looked up. We get seated, all the while still on her phone texting. So I asked her normal date things to only get «yes» and eventually a «hold on a second» after my third attempt at striking up any sort of conversation.
    I asked if everything was OK because I figured after the «hold on a second» comment, something bad might’ve happened. She responded by saying her friends are a priority. I was kind of taken aback. Our waitress walks up right after that, and she cuts her off as she’s greeting us with a huffy, «Finally!» Then barks her drink order at her as rudely as possible and goes right back to her phone.
    I asked for water, said «Excuse me» and got up after about a minute of silence. I found the waitress, gave her a 20, and said I was leaving, and apologized. Quickest date of my life. All in 10–15 minutes max. I’ve never met anyone close to that rude on a date in my life. I always tell myself I got all my bad dates in one. Here’s to hoping that’s true! © Unknown author / Reddit
  • Went to pick up my blind date. She opened the door, looked at me, and said, «Ew.» I looked at her and said, «Yeah, I agree,» and turned on my heel and left. The total date time was less than 5 minutes. © Outlander56 / Reddit
  • I don’t do anything expensive for first dates. My go-to is walking around a public lilly pad garden, then playing mini golf around the corner. Sometimes, based on the interests in her profile, I’ll do something different, like going to a museum or the planetarium.
    I met this great girl, and we hit it off. Based on her profile, I thought she would love the South American exhibit at the local museum, so we went there for our first date. We got banana splits afterward, and I thought it was a pretty good date. I was looking forward to seeing her again.
    She had some work stuff then I had some work stuff, but after like 3 weeks we made it happen. We were going to see a movie and go eat at a little restaurant, but she was 30 minutes late, so we just went to eat. She spent the first 10 minutes talking badly about the «last guy» she dated who took her to a stupid museum, and then out for a banana split. She complained that her last date was too cheap to buy her dinner «like a real man». She kept talking and talking and talking.
    I excused myself from the table, paid for my drink and half the appetizer, and left. Blocked her on the app and phone.
    And if you’re wondering how she didn’t realize the «last guy» was me, she spent most of the time staring at her phone and I had shaved my 10-day beard off due to an interview© Nevermind04 / Reddit

Navigating the world of dating is always a rollercoaster ride, whether you’re single or in a committed relationship. Even if you’ve been with your partner for ages, they can still catch you off guard with something completely unexpected, whether it’s a delightful surprise or a not-so-pleasant shock.

Preview photo credit Capitolkid / Reddit


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