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Strange First Date Stories, As Told By The People That Suffered Through Them


Despite what romantic comedy meet cutes have led us to believe, first dates tend to always be plagued by awkwardness. Going out with a complete stranger can lead to some seriously strange situations. While some first dates are followed by many more, there are others that end right then and there.

Anyone who has dipped their toes in the dating pool will have at least one date that took a turn for the bizarre, which is why one Redditor asked the community to share stories of the weirdest first dates they’ve ever been on.

If you thought you’ve had some peculiar dating experiences, wait until you read these 25 unbearably cringeworthy first date stories.

1. Introductions: “An acquaintance from school asked me to go to the movies with him and to be honest, I didn’t even know it was intended to be a date. We had a pretty good time and he asked me if I wanted to go play some games at his house after so I said yes. As soon as I walked into his front room I was met with about 8 of his family members. He had invited over most of his family to meet me. They all believed I was his girlfriend and that we had just come back from a date. It was very uncomfortable but I did not have the heart to say that we weren’t a couple.” (Reddit user: Sammie_SU)

2. Litter Bug: “I met a guy from online for coffee and walked the beach. Immediately, things did not go well. We disagreed about pretty much everything and he even had the nerve to mock my religious beliefs. After our walk he asked if I wanted to sit on the beach. I couldn’t believe he wanted this nightmare to last longer, but I obliged awkwardly. He set his coffee cup down in the sand and it blew away but not very far. I said, ‘Oh no your cup.’ He looked at it, shrugged and said, ‘I litter all the time. Yeah, like if I have an empty McDonald’s bag, I’ll just throw it out the window. That’s what prisoners are for.’” (Reddit user: AbbyVanBuren)

3. Somber Setting: “I met a guy at the skate park when I was around 14 years old and he asked me if I wanted to go out with him the next day. I thought he was gorgeous so I happily obliged. He told me specifically that I should dress up so I was expecting something really special. He took me to his little sister’s funeral.” (Reddit user: [deleted])

4. Table Manners: “I went to a Japanese steakhouse with the most embarrassing date I’ve ever had. She started by heckling the chef and then threw pieces of food at the next table. I’m pretty sure she had drank a bit before our date and she clearly did not handle alcohol well. She managed to piss off the chef to the point that he doused her plate, set it on fire and then just walked away. Plate was completely engulfed in flames.” (Reddit user: [deleted])

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