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Craziest Things That Have Ever Happened On First Dates

First dates can be so nerve-wracking that they can lead to some hilarious moments that you can’t help but laugh at years down the road.

In this article, you’ll find a few hilarious dates that went horribly wrong. Maybe you’ve had a similar experience as well?

© lakeshoreentertainment

My friend looked for a boyfriend after her divorce, hoping to prove to herself that she was still likable. She met a man. And it was winter, they had a lengthy walk. He then stated that he was hungry. She smiled and assumed they’d head to a restaurant. Another lengthy walk, and they arrived at an apartment complex, where he remarked at one of the doorways, “Please wait for me here. I’ll go home, have a fast snack, and then return.”

© paramount

My boyfriend wanted to purchase some ice cream for me. I went with the chocolate flavor. He drove me home four hours later, after a great walk together, and at the most important moment, I felt shy. He unexpectedly inquired about the prominent aspects of my face. I had no idea what he meant. He clarified by saying that even if I had more birthmarks there, it wouldn’t matter because he still thought I was handsome, and that there was always medical therapy available to remove them. I waved goodbye, then returned to my apartment and noticed in the mirror that I had a big brown chocolate ice cream stain on my cheek.

© dreamworkspictures

On my very first date, I took my girlfriend to a karaoke night and she chose to perform Whitney Houston’s “I Will Always Love You,” and she did an excellent job. It would have been OK if she hadn’t announced to the entire audience before the song began that she was dedicating it to her ex-boyfriend.

© sonypictures

I proposed to my boyfriend that we go see an art house film. We arrived at the movie theater and the film which was about to be shown was Shortbus. There was no information or reviews about it online so we just purchased our tickets and took our seats. My boyfriend didn’t speak English as his first language and reading subtitles was essential for him to understand the movie. But the worse thing was that he was even short sighted. When I apologized, he reassured me that it didn’t matter as long as the movie was good. The film began, and the first scene was something that was insanely shocking. The camera gently panned backward, revealing that it was a specific section of a man’s anatomy. At this point, the man exited the bathtub and began masturbating. The film turned out to be about a nymphomaniac with an older lover, and it was full of intense scenes. I recommended we go, blushing profusely, and we were both really uncomfortable. This has to be one of the worst times of my life, I reasoned. But, as it turned out, this was not the end of my problems. We were walking to the subway after the movie when I became quite ill. It appears that I had gotten a stomach illness that had been going about. “Would you mind if I throw up now?” I almost exclaimed. He was green and sweaty as he took me to the metro. We never went on another date after that. But looking back on it now, it’s amusing.

© mgm

A pigeon pooped on me ten minutes before our date began. That day, I discovered that bird poop stinks. I opted not to tell my date what had happened, but there was a very terrible odor in the air surrounding me the entire time. Not a nice first impression.

I took a girl to Starbucks because I was too anxious to remember her name. 

© cbsfilms

I went on a double blind date once. To set me up, my pals urged me to bring a red wine bottle. So when I arrived at their house, I instantly tripped and fell, breaking the bottle against a sofa corner. Our relationship ended right there, before it even began.

Preview photo credit depositphotosdepositphotos, Brightside | Based on materials from marieclaire


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