CheezCake

Worst First Dates People Have Ever Been On

  • 1
    Font - Posted by u/Frekkes 1 year ago What is the worst first date you have ever been on or seen? At lunch today I was sitting next to a couple and a friend of there's that they were setting up a blind double date with. Dude was wearing "black rifles matter" shirt and when the girl arrived she was in a "march for our lives" shirt. It was the most quiet, awkward, fast lunch date I have ever seen. So what are the worst you have seen and/or been on?

    We got the OP kicking the post off with a cringe first date story of their own. They could have discussed their difference in opinion at the very least? Try to make it work through an intense debate where they end up passionately making out? No? Okay. 

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  • 2
    Hair - [deleted] · 1y My friend was asked by a date (very early into said date) 'Are you on your period? I have this strange talent where I can always smell when a girl is on her period' She picked up her bag and left immediately.

    So many red flags here! This strange superpower can be perceived as both a blessing and a curse, but why must he bring it up on a first date?! Relieved out girl got outta there STAT. 

  • 3
    Font - roachezmo Had a girl try to convince me to cut off my long hair for the date. The first date. She knew I had long hair, it wasn't a blind date. She also brought her dog unannounced, insisted it go into the bar with her, then only talked about money for the next hour or two, constantly pestering me about how much I made. The second I caved in the date was over. Ms. Moneybags still let my apparently broke ass pay the tab. One girl started crying when a certain song came on and demanded to b
  • 4
    Font - Platemails · 1y 2 Matched with someone on tinder, we chatted a couple days on and off, we eventually decided to meet at the bar, she spent a lot of time on her phone, seemed extremely eager/anxious, looking at the front door of the bar, people kept walking by us and saying hi to her so this was obviously her watering hole, we got one drink in before whoever she was messaging/eagerly awaiting arrived, she excuses herself for "just a second" 10 minutes later she still isn't back, the barten
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  • 5
    Font - airmaildolphin · ly I asked a college girl out for dinner and to see a play and she invited her mother along. It was so awkward.
  • 6
    Font - BigShoots · 1y S 2 I was walking past a rickshaw one night with a dude and a lady in it, and the lady says, "I always feel bad for these guys, I feel like I'm too heavy." %3D And instead of reassuring her the guy says, "Oh don't even worry about it, these guys could carry a moose!" I think he knew as soon as it left his mouth that he wasn't getting anywhere on that date.
  • 7
    Font - cornbadger · 1y I have a female relative who's started dating a guy. He's driving her home and is talking on his phone. He's having a terrible fight with his ex. Apparently at some point he loses his mind and tries to kill himself by ramming the car, with my relative still in it mind you, into a telephone pole. He missed and put the car into a ditch. They both lived. She married him four months later. Big surprise: he was an abusive psychopath. It lasted less than a year.
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  • 8
    Font - Brak23· 1y Male I was in Maui for vacation and walked over to eat at a restaurant near my hotel. I sat next to this couple who were just sitting down as well and they had some light small talk and ordered drinks and food and stuff. He pulls out his phone and records a snapchat video of her and saying "This is my friend from Utah" and it all seemed like they were hitting it off, then it got weird. He appeared to lose his ability to strike up any conversation, he kept re-watching the video
  • 9
    Font - PM_Me_Your_Nacho · 1y 3 She was really superficial and vapid. Gave a list of what a "real man" has to have in order to be with her. List was like have a Mercedes or bmw, wear a Rolex, have a suit, own their own home, have a condo in the city for weekend fun, own a boat, has to have an inheritance, can't be more than 2 years older than her. I was pissing myself laughing in her face because she was an 18 year old freshman in college and believed this was a pre requisite to date her. She's h
  • 10
    Font - [deleted] · 1y First date back into the dating scene after being out of it for 14 years. It had changed, a lot. So I go out with a girl from one of the apps. Have a great time, we part ways for the night. I get a slew of angry messages why I didn't make any moves or invite her over after. Like crazy texts. Nothing about anything physical was discussed prior and the last time I went on a first date was just before I had turned 17. So at 31, i was not in the know about the hookup scene. Her
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  • 11
    Font - mophilda · 1y Good date. Having fun. Good conversation. Enjoying the nice spring weather on the porch of a Mexican restaurant. We have just asked for the check and then a woman shows up and threw her keys at his face. He pretended it didn't happen. It comes out (pretty quickly) that this was his girlfriend. They get into a right proper fight in the parking lot and the cops show up. I can't leave because my card is inside with the server and it's taking 1000 years.
  • 12
    Font - MysticYounger · 1y Male Blind date The girl was really hot but 1. She has anger issues 2. She was currently on probation for assault 3. Her ex bf is in prison 4. She lives 2 and half hours from me
  • 13
    Font - PeejWal · 1y · edited 1y Oh I got one. Met a girl on Tinder, chatted for a couple weeks. She comes over to my house to hang out and watch a movie. We smoke a little bit and decide to find a horror movie neither of us had seen. We chose "Maniac" with Elijah Wood in it. So we get all settled in, turn it on, and the first scene of the movie is Elijah meeting a girl online, her going to his place, and him murdering her. there was not a second date
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  • 14
    Font - colojason · 1y Back when I was single my friends wife hooked me up with a woman she worked with. Said she was cute. She wasn't. She spent the whole date talking about how she hadn't had sex for 17 years and she had only had sex with her college boyfriend. There was zero interest on my part so I chose not to pick up on the hints. It was our only date.
  • 15
    Font - harrison1454· ly Male Story from my friend. She went on a tinder date. He kept vaping into her face at a restaurant asking if she was impressed by the large clouds.

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Abby is a wandering soul who is incapable of staying in one place for too long. Her passions include travel, dance, karaoke, meditation, and cheesy fries. When she's not clacking away at her laptop and talking shit on the internet, you can find her tearing up the dance floor on a night out on the town.

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About the Author

Abby is a wandering soul who is incapable of staying in one place for too long. Her passions include travel, dance, karaoke, meditation, and cheesy fries. When she's not clacking away at her laptop and talking shit on the internet, you can find her tearing up the dance floor on a night out on the town.