12 Dating Horror Stories That Will Make You Happy To Be Single For The Holidays

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Being single around the holidays can be tough, but even with a zillion dating apps, the holidays make dating even tougher. But don’t despair — the following dating nightmare stories, as collected by The Huffington Post, will make you feel juuuuuust fine about masturbating underneath the Mistletoe!*

*Please don’t actually masturbate under the Mistletoe. Unless you’ve attached the Mistletoe above your bed. In that case, you may proceed.

She’ll Have to Get Back to You

“Had a guy who referred to himself in the 3rd person the entire date. He ordered drinks and appetizers etc. (I don’t drink, at all). At the end of dinner he said we’ll split the check down the middle. Then he asked me if ‘Autumn wanted to go back to Eric’s place now’ to which I replied, ‘I’ll have to ask her and get back to you.'” (source)


Who’s His Mommy?

“We were having coffee talking about the area we live in and where we grew up when he changed direction with the conversation and asked if I liked diaper play. I was dumbfounded. He went on to say he liked to wear them. I came down with a headache real quick and left my coffee sitting… running to the nearest exit.” (source)


In and Out

“Met a guy I’d been talking to on a dating site for our first date at a bar. We ordered our drinks and he immediately paid, chugged his beer, looked me up and down and said ‘yeah… I can’t do this,’ and left me there.”


The Big Surprise

“Went out with a guy I had been talking to for a while… He told me to come to his house for a ‘big surprise’… I get over there and there’s about 50 people I’ve never seen before on his lawn. One guy was standing in the middle giving a casual presentation… It was a pyramid scheme. The guy had invited me over for a pyramid scheme.”


Happy Birthday

“It was his birthday, so I offered to take him out to a nice rooftop restaurant. The drinks came and one of them spilled on the table, he stopped the waitress from wiping it up and proceeded to slurp it off of the table and said ‘these drinks ain’t cheap’ (as though he was paying). Then he spent the rest of the night on his phone.”


Mo Money Mo Problems

“This guy asked me out to dinner, and we had great conversation, great beer, great food. The waitress drops the check, and it sits at the table for probably 10 minutes and he hasn’t offered to pay, so I figure we’re going dutch, which is fine. So I put down my half and hand the check to him. That’s when says he doesn’t have any money (in our conversation, he’d mentioned he has two jobs). I say, “You’re seriously doing this? That’s a pretty ballsy move.” He tells me, “credit cards are evil.” I ask if he has any cash then. He says no, and to prove this, he takes his wallet out of his pocket, counts out $23 in cash, says “See? I don’t have any money,” and PUTS THE CASH BACK in his wallet.”



“I had dinner and great conversation with a man I met online. In front of my apartment, I thanked him again for treating me to dinner, and he asked if he could kiss me goodnight. I said yes and we had a hot first kiss. Then he paused to ask if I would be willing to urinate in a glass so he could drink it. I guess I’ll have to think about that — from the other side of my locked apartment door!”



“I met this guy online and agreed to meet up for dinner that night. A few hours later, he texts to tells me he is in the hospital and asks me to come visit him, but won’t explain why he’s there. I agree, thinking maybe he broke his leg or had a car accident on the way to dinner? When I arrive, I discover he’s there because he tried to kill himself when he found out his wife wanted a divorce! I’m feeling terribly awkward I trying to come up with an excuse to leave when his family arrives… and he tells them I’m his girlfriend. I left, and for months afterward he continued to text and call me while I ignored him.”


Two Thumbs Way Down

“We made plans to go to a movie and then get coffee afterward. I offered to pay for the movie if he sprung for the coffee. We were supposed to meet at the movie theater, but he was 20 minutes late, so we missed the movie. I was pretty annoyed but tried to let it go as we walked to the coffee shop. As soon as I order my mocha, he pipes up, ‘Since you got out of paying for the movie, why don’t you get the coffee?'”


Fair Warnings

“So, I met this guy at a club, he was cute, and we exchanged numbers. He started texting me a lot and asked me out for coffee. We made pleasant small talk: stories about our childhood, sports, favorite TV shows, etc. Then he adds that he always has to fart — when he’s in the car, at the club, in restaurants, and every time he sits down. I don’t say anything, so he follows it up, ‘Actually, I need to fart right now,’ and lets one loose in the coffee shop, which I could hear. I said I had a family dinner and and left.”


Dancing With the Stars

“I knew the guy was health-conscious, but when I ordered a chicken salad, he proceeded to inform me that I should not eat the cranberries or vinaigrette dressing due to their ‘overly high sugar content’. After the dietary lecture, he started talking about the contestants on that season’s Dancing with The Stars. The conversation turned to people who overcome physical disabilities to rise to stardom, and he looked at me square in the face and said, ‘Oh, you mean like Helen Keller… wasn’t she on Dancing With the Stars?”



“I met up with this guy I had been chatting with online, and after a beer it was clear there was no chemistry. He offered to pay, which I thought was nice, said he needed to get cash, and walked down the hallway to the ATM. I could see the corner of him standing there for a few minutes, then and he came back, paid, and we said goodbye. A few nights later I end up back at the same bar, out of cash, so figured I’d use the ATM. I walked over to where my date had stood and saw there was nothing there, so I asked the waiter about where they’d moved the ATM. He told me they’d never had one. I’ve heard of people who fake other things, but never getting cash out of an imaginary ATM, and I now have no idea what my date was doing.”


Do you have a dating disaster story?

12 Dating Horror Stories That Will Make You Happy To Be Single For The Holidays


One reply on “12 Dating Horror Stories That Will Make You Happy To Be Single For The Holidays”

I got an ordinary massage the other night and we start talking about philosophy and it turns to sexual philosophy. Before I know it she has my dick in her hands and we get it on. At the end I ask her “How much extra?” and she yells at me “I’m not a whore! Get the fuck out.” So I scramble to get my clothes on and leave reeking of sandlewood oil. I barely get back to my car and she calls to tell she’s sorry and I’ll get a a free make-up massage if I come back within a week. Same shit happens. I’m no stud with washboard abs and a big dick; I just think she’s a crazy woman with an itch that needs scratching and TBH, I’m afraid to go back. There is nothing more expensive than pussy that is given for free.

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