11 First Date Horror Stories That Will Make You Cringe

11 First Date Horror Stories That Will Make You Cringe

Think you’ve been unlucky in love? Check out these hilariously terrible first dates.


By: Nicole Fabian-Weber

Bad dates – we've all had 'em. At the time, they're pretty excruciating, but when we've healed from the trauma and they’re nothing but a distant memory, they make for one heckuva story. We asked women for their worst date stories, and goodness, did they ever deliver. Fortunately, these ladies have all recovered from the following events, but no doubt, it took some time.

Here, 11 hilarious first date horror stories. Thank goodness we can laugh about them now!

1. "No joke – I once went on a date with a guy who brought his mother along. She was a lovely woman, but seriously?!?!" -- Annie G., Denver, Colorado

2. "When I was in college, I brought my date back to my place. However, I had forgotten my key. Because it was super late, no one was home to let me in, and I didn’t know how to break into a window, we wound up hunkering down in his car on an absolutely freezing night. He would run the heat on and off occasionally for reasons I can’t remember. We slept in the car until someone returned to the house in the morning." -- Kiri B., New York City

3. "I met a guy from a dating site at a bar. He seemed perfectly nice, but he resembled my brother. Everyone says you’re attracted to men who resemble the men in your family. But you know what? There’s a limit to that theory. I pulled away when he tried to kiss me, because it was that bad, and I cut the date short. Oddly enough, a couple months later he texted to wish me a 'Happy Halloween!' Why? Was he wearing a costume that made him look less like my brother?" -- Adriana V., New York City

4. "One guy I went out with keyed the car next to him in the parking lot for parking too close. We never went out again." -- Laura L., Los Angeles, California

5. "I once went on a date where we met up with a bunch of his friends at a bar. The guy I was supposed to be out with had his friend drive me home because he wanted to stay out! Nice, huh?" -- Erin M., Los Angeles, California

6. "I went on a blind date with a guy I'd met through a website. We met at a restaurant that he picked out, and after an hour of (awkwardly) talking I asked him if he wanted to order food -- to which he acted completely, totally surprised. How silly of me to think I was going to eat at a restaurant!" -- Ilene P., Manalapan, New Jersey

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7. “I knew this guy for a little while and we decided to go on a date. Thirty minutes before our date, I started throwing up -- turned out to be food poisoning! He actually stayed a little while and we chatted between my barf sessions. So awful but yet kind of nice of him to stick around.” -- Sheri R., Sacramento, California

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8. "I went out on my first date since splitting with my husband. Local single dad -- very handsome. Turns out, he's my soon-to-be-ex-husband's ex-wife's stepbrother! He was at my ex's FIRST wedding! My first date in 11 years and that is what I get?!" -- Julia H., Pittsburgh, Pennsylvania

9. "Years ago, I went out with a guy and both of us ran into our exes at the restaurant we were at! I guess that's more just strange than bad. I mean, what are the odds?!" -- Lisa W., New York

10. "My friend set me up on a date with a guy she worked with. She swore he was 'super cool.' Um, not so much. The entire time, he bragged about how much money he made -- and then when the bill came, he asked me for money! Normally, I wouldn't mind going dutch, but it was a little ironic after talking about his money all night long." -- Erin S., Westfield, New Jersey

11. "I'm lactose intolerant and the guy I was out with (who I had a major crush on) ordered nachos for us to split. I didn't want to be the 'girl-who-doesn't-eat,' so I had a few. I won't get into details, but sadly I had to make up an excuse and cut the date short. We never went out again." – Shannon S., Brockport, New York

What's the worst date you ever had?


Nicole Fabian-Weber is the mama to a sweet toddler girl and an equally sweet baby boy. She lives outside of NYC and writes for The Stir and numerous other online publications.

Image ©iStock.com/Maica


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