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Dating Nightmares: Women Reveal Worst First Dates With Cheapskate Douchebags

stories of first dates with cheapskate douchebags - cover pic pop art pic of man look at empty wallet | l had a date at Starbucks, but when I arrived, the guy was already holding a cup of coffee from McDonald's. He told me Starbucks coffee was too expensive for him, so I had to wait in line to buy myself a coffee.
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Ah, that awkward, age-old debate of who should pay on a first date. Some argue that splitting the bill is best, because hi, welcome to equality. Others believe that chivalry and feminism can peacefully coexist. They maintain that although a woman should always offer to pay her half, men are expected to decline the offer politely and insist on paying. But no one talks about secret option C, where the guy flat-out refuses to pay at all.

Together with The Single Society, we bring you stories from real women who went on dates with total cheap-ass douchebags. From those who refuse to leave a tip to those who try sneaking their own alcohol into bars, these stories reveal the worst type of men to go on a date with. Guys, frugality is not a cute look on a first date. Ladies, have you experienced cheap ass first dates?

  • The Stingy Tipper

    Hair - TEPIG YOU'RE CHEAP.
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    "One time I went on a date with a guy, and he asked me to split the bill at dinner. No problem! We went to another place after and had a bottle of wine and dessert, but when the check came, he conveniently went to the bathroom. For some reason, I just paid it myself. When he got back, he told me he would leave the tip and threw a few coins and a ball of lint on the table. I threw down some cash because I felt bad for the bartender, and my date told me that he thinks tipping is ridiculous because it isn't his fault bartenders don't make a salary."


  • The Man With A Van

    Facial hair - CHECKMA I lived in a van with a blow-up mattress
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    "I went on a Tinder date with a guy who ended up living in a van. At the end of the date, he asked me to smuggle toilet paper out of the bar in my purse. THEN, he walked me home and asked me if he could use my shower."


  • The Lotto Loser

    Hair - WHAT KINDA BULLSHIT ISTHAT?
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    "On my first (and last) date with a guy, he asked me if I had any cash so he could run in a convenience store and buy something to drink. All I had was a $20 bill, which I handed to him. He came out and handed me two one-dollar bills and a few dimes/nickels. Not only did he use my money to buy himself a drink, but he also bought a can of chewing tobacco and some lottery tickets."


  • The Cheapest Ass Out There

    Face - I detest cheap sentiment
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    "A guy showed up 45 minutes late for a date and admitted he was driving around trying to find a free parking spot because he didn't want to pay $5.00 to park in the lot across the street. He then got in a fight with the manager because he wouldn't let him drink the wine he brought as the establishment was no longer B.Y.O.B. When the check came, he didn't even acknowledge it, and I ended up paying for it just to get the f*ck out of there."


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  • The Dumpster Diver

    Countertop
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    "I went on a movie date with this guy. He went up to the garbage can and grabbed a discarded extra-large popcorn tub out of it. He then took it up to the snack bar and got it filled. Apparently, if you bought a big tub, it came with free refills, but instead of buying one himself, he just took one from the trash. He also smuggled a bottle of Pepsi in his jacket."


  • The Cappuccino Cheapskate

    Blond - OVER THIS SHIT
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    "I met a guy at Starbucks for a date. When I arrived, he was already holding a cup of hot coffee from McDonald's. He told me he wanted to get his coffee there because Starbucks coffee was too expensive. I then waited in line to buy myself a coffee."


  • The Work Benefits Exploiter

    Fun - FIFTY BUCKS? I COULD TAKE... TWENTY-FIVE WOMEN OUT TO DINNER!
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    "Met a guy on Tinder. He told me to meet him for a date at this place that turned out to be a meetup for his industry, which had an open bar. After we left, he took me to the hotel where he worked. I offered to split the check. He said he would take care of it and left for 15 minutes. When the guy came back, he told me that he actually DID want to split it because he thought the manager that he was close with would be there to comp the entire bill, but he wasn't. While signing the check, he said, "Well, I thought I was going to get through the night without spending any money at all, but I guess $25 isn't so bad, right?"


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  • The Movie Moocher

    Suit - The Prea herin very convenient.
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    "I went to dinner and a movie (or so I thought) with a guy my mom set me up with. When we got to the theater, he suggested I pay for the movie tickets and he would pick up dinner. Seemed fair. He also conveniently ran to the bathroom as I stood in line and bought the snacks. After the movie, he told me he wasn't hungry."


  • 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.