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Dating Nightmares: Weird Things Men Have Done On First Dates

Weirdest Things guys Have Done On First Dates - thumbnail pop art image of man and woman in car would you mind blowing my... breathalyzer | My date had a breathalyzer installed in his car because he had several DUIs. He assured me he would be able to drive, but when he wasn't he asked me to blow into it so his car would start
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If 2020 has taught us anything, it's that no matter how bad things seem, they can always get worse. This sentiment can also be applied to the sh*t show that is modern dating. You may think you have been on some bad dates, but they can only be worse! We teamed up with The Single Society to show you exactly how awful this sh*t show can be. Here are some examples of the weirdest things guys have done on a first date!

  • The Fingernail Clipper

    Fashion - #YOUNGERTV THAT'S DISGUSTING
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    Went on a date with a guy. I walked up to the table and he was clipping his fingernails. When he saw I had arrived he swept them off the table and stood up to give me a hug.


  • The Lotto Loser

    Floristry - Where's my money?
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    Met up with a guy for a first date and we were going to walk around downtown and pick a spot to eat. He said he was thirsty and wanted to buy a Gatorade. He asked me if I had any cash. I gave him $20. He came out with a Gatorade, chewing tobacco, two lottery tickets, and a few small bills. He stuck the bills in his pocket. He kept the f*cking change. You can read about this nightmare of a date here!


  • The guy who totally BLEW it!

    Photo caption - Mic .. If you drive drunk, you, simply put, are a short-sighted, utterly useless, oxygen-wasting, human form of pollution.
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    My date had a breathalyzer installed in his car because he had several DUIs. He assured me he would be able to drive, but when he wasn't he asked me to blow into it so his car would start. Read about this disaster date here.


  • The guy with a heavy cash flow

    Hairstyle - THANK YOU?
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    After an all-around awkward date with a guy I met online I was about to head to the subway and he said 'Oh, I should probably be chivalrous and get you a cab." I told him it wasn't necessary but he insisted. Then he said, "I forgot my Uber app on my phone is messed up. Here is money for a cab, I guess," as he walked away. He put a $100 dollar bill in my hand then left me on the sidewalk to grab a cab myself. Not exactly what I'd call 'chivalry'…but, thanks??


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  • The flashy show off

    Hair - - GRVE UM...
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    A guy picked me up for a date. He said he had an 'errand' to run. He pulled into a strip mall and took me inside a jewelry store to take a look at a $10,000 watch he was looking at. He didn't buy it, he just wanted me to see it. 


  • The Pokémon Catcher

    Chin - Are you fucking kidding me?
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    A guy I was on a first date with excused himself from the table because he needed to go catch a rare Pokemon. He was playing Pokemon Go the entire fucking time.


  • The drunk who fell asleep on the date

    Photograph - WASTED
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    A guy I went on a date with was clearly drinking all day before meeting me. He excused himself to go to the bathroom and fell asleep on the toilet. 


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  • The guy who brought out pictures of his ex

    Neck - Tucone Isn't that so, cute. #InTheCut T
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    This asshole pulled out his phone while on a date and showed me a picture of his ex-girlfriend who is apparently an Instagram model.


  • The Topless Showoff

    Hair - Foim TAXOIT DOCRSG N
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    A guy I met pulled into my apartment complex to pick me up in his convertible. When I exited the building he opened his car door and stood up. He was shirtless. He had an extremely (and obnoxiously) muscular physique and apparently he wanted me to see it.


  • The Mommy's Boy

    Hair - ABEAL
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    His mom Facetimed him in the middle of our date. He had a several minute conversation about how his day was then turned the phone around and introduced us


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  • The Cappuccino Cheapskate

    Hair - You're kidding. Please tell me you're kidding.
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    Met a guy for the first time at Starbucks. When I showed up he already had a hot cup of coffee from McDonald's. He said he grabbed it on his way because Starbucks' coffee is way too expensive. More on this cheapskate here.


  • The Delusional Musician

    Hair
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    I went to a park/picnic date with a guy after the quarantine ended. He brought a guitar and just kept playing it and singing to me. He had no talent whatsoever. It was really f*cking awkward.


  • The Public Pisser

    Singing
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    After getting a few drinks with a guy I met on Hinge he offered to walk me to my car. He said he had to go to the bathroom. He walked toward an alley, unzipped his pants, and took a piss right in front of me.


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  • The Toilet paper Thief

    Hair - WHAT KINDA BULLSHIT ISTHAT?
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    On a date with a guy and he excused himself to go to the bathroom. When he returned he asked me if I would shove several rolls of toilet paper in my purse and smuggle them out for him because he was running low. Read about this trainwreck of a date here.


  • About the Author

    TheSingleSociety
    Nikki is currently living in NYC with her husband (who she met on Bumble after experiencing the absurdity of online dating) and working in digital marketing. She clearly enjoys recording the ridiculous debauchery that is the modern dating scene. Nikki is also partial to a tall glass of Prosecco, her black/calico kitties, 90s music and playoff hockey. Drop her a line if you have a good story for her to write about.
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About the Author

TheSingleSociety
Nikki is currently living in NYC with her husband (who she met on Bumble after experiencing the absurdity of online dating) and working in digital marketing. She clearly enjoys recording the ridiculous debauchery that is the modern dating scene. Nikki is also partial to a tall glass of Prosecco, her black/calico kitties, 90s music and playoff hockey. Drop her a line if you have a good story for her to write about.