41 Men And Women Share The Most Insane Dates They’ve Ever Had To Suffer Through

19. One Date=One Relationship

A guy I’d met a few times contacted me asked me on a date. I had never been asked on a date before and accepted despite thinking him a little strange and having heard some odd things about his family.

He picked me up and everything seemed good, we decided to grab a pizza and eat it in a park. When we went to purchase the pizza, it turned out he worked there and had all his co-workers come out to gawk at me. (This guy wasn’t very popular with the ladies and seemed to be proving he had a date). I’m bad in social situations and got super uncomfortable, but didn’t know how to bail and we went to the park.

It was very awkward and I wanted to go home by the end of it. We mostly just sat in awkward silence and tried not to hear each other chewing. I thought I was going home, but he decided he wanted to stop at his house. I agree because I honestly did not know how to disagree. (First dating experience). His home turned out to be with his parents. (We were both 18-20). This wouldn’t have been so bad had they not had all ten of his siblings (I don’t remember exactly how many siblings he had) and his parents were home and wanted to meet me.

They weren’t just a big, nice family, they were very religious and looked like they belonged to a cult. They all had long hair, homemade clothing, they were home-schooled. The mom said hello, then the dad came in and nobody was allowed to say a word while he questioned me on what me and his son had done on our date and when the family would be seeing me again. It was terrifying. My date showed me his pet turtles, which were really cute, and finally drove me home.

He tried to kiss me after making it clear he thought we were in a relationship after one date. At this point, I almost ran from the car. I messaged him later on explaining that I was only looking for friends at this point in time.


20. Possibly A Mob Front

Well, this one time I took my date to dinner at (what seemed to be) a front for some type of illicit activity.

We had just moved to a new area, and we wanted to check out the local shops and restaurants. While we were wandering, we stumbled into a tiny Italian place. Back home, the small hole-in-the-wall restaurants always have the best food, so we were excited to give it a shot. Big curtains were covering the entry windows, so we had no idea what was inside until we trudged through the door.

Inside, we were met with emptiness and silence. We both immediately thought the store was closed, and I spun around and searched for the store hours posted somewhere on the door. While I was looking, we heard a heavy THUD as a young woman barked “I’ll be right with you!”

She appeared, greeted us confusingly, and asked us ‘what she could do for us’. Which, looking back, is probably a red flag. But we were naive and hungry, so we said we were there for dinner. She looked puzzled but motioned us to follow her to a booth right by the entrance.

She then disappeared into the back, and we heard a muffled conversation between our hostess and a man. The consensus was basically they were not prepared for us or didn’t know how to proceed. I asked my date if she wanted to split, but she insisted we stay for the story.

The square shaped balding man burst through the kitchen door with two glasses of water for us, and in a very loud and deep voice, he explained that it was his birthday, and we would eat what he felt like making us. We whole-heartedly agreed.

We waited around thirty minutes, and he again returned with three large bowls of spaghetti and meat sauce. He placed two bowls in front of us, and one next to me for himself. He sat with us and ate. We had light and awkward conversation with him during, and he kept asking us jokingly if we were cops or with the health board. He was incredibly nervous about us, so my date kept cracking corny puns or awful jokes because he would forcibly laugh at anything designed with humor. We talked about our lives, the cities we’ve lived in, our pets (he had a teacup Chihuahua named Princess) and his wife.

He decided we were good people and didn’t charge us for the meal. We wished him a happy birthday, he hugged us, and we went on our way. Easily the best spaghetti I’ve ever had in my life. The restaurant, unfortunately, no longer exists.



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