Embarrassing Dating Stories That Will Make You Laugh Or Cringe!
Have you ever been on an embarrassing date you just want to forget? If you’re still in the dating scene in today’s modern world, chances are you have experienced how dating can be a daunting affair! With nerves on the rise, expectations, and well, the pressure to put your best foot forward while getting to know a brand new human can create some embarrassing situations.
5 people share their own embarrassing dating stories that will make you laugh or cringe!
Embarrassing Dating Story #1
The Ego
A man I had a first date with was so into himself as he talked about himself all night at the dinner table. He asked me if I liked his watch, which at that point, he revealed to me it was a $20,000 birthday present to himself.
He likewise revealed to me that he could pleasure himself better than any lady. At a certain point, he even asked the older ladies sitting beside us if we made an attractive couple. They said yes. His response? ‘That is correct ladies, you can also buy a date with me online!’ I was so humiliated, apologized to them, and said he was correct-you can purchase any sort of crap online.
Embarrassing Dating Story #2
I Love You
I had been dating this guy for about a month, and we decided to meet at a popular club one night. I was running late but eventually got to the club where I found him on the dance floor bumping and grinding up on some girl. He notices me, and comes over and tries to get me to dance with him. I really wasn’t in the mood, and instead of me leaving the club, he said he needed to tell me something. It seemed pretty serious, so I obliged and he brought me a drink at the bar.
I noticed he was a lot more talkative than normal, as I thought he was the shy and reserved type, but I just thought it was the alcohol talking. Then he proceeds to tell me he’s in love with me! I didn’t know what to say, but luckily the long awkward pause was interrupted by him falling off his bar stool. At that point, I just freaked out and bolted!
Eventually I found out he had taken some ‘Molly’ in the male’s toilets while waiting for me, but still, I couldn’t face hearing another “I love you” from him again.
Embarrassing Dating Story #3
The Coughing Fit
I was at dinner with a man I met online when he had one of those horrible coughing fits that wouldn’t stop. I gave him some water, offered him napkins, and kept asking if he was OK, as I needed to be assured he didn’t require the Heimlich!
Now, if I were him, I would have just gone to the bathroom. But he just sat there choking, while spitting food up onto both of our plates! He finally stopped and drank some water, and after that, he just began to eat once more! He clarified the choking by saying he’d eaten a portion of his napkin. How does that occur? I was horrified. I powered through my dinner, and when we left the place, he attempted to kiss me. I dry-heaved all the way home and ignored his following messages.
Embarrassing Dating Story #4
BOO-WHO?
A girl I had been seeing was heading to a children’s museum with her younger sister and requested that I follow along. I didn’t feel like it, yet I could tell that she truly wanted me to go, so I did. But, when I began looking at the exhibits, it ended up being really fun.
There was an exhibit about the pyramids, and it had a giant maze attached. I wanted to play a joke on her, so I ran in front of her and her sister and hid behind a wall so I could jump out and scare them when they walked by.
When I heard them coming, I jumped out and shouted, ‘BOO!’ without warning, an old lady shouted and the little boy she was with began crying! Turns out, I jumped out too early. I felt so bad, yet my girlfriend and her sister couldn’t stop laughing at my embarrassing situation.
Embarrassing Dating Story #5
The Cheap Date
A few years ago I met a guy on Tinder and after a few weeks of talking online, he decided to invite me out to a fancy restaurant. I was cool with meeting him somewhere else, but he insisted it would be fun, so I was delighted to accept.
We got along well over a three-course meal and some nice champagne. It wasn’t until dessert however, he started complaining heavily to the waiters about how disgusting his lemon meringue pie was. He demanded they take it back or give him a refund.
They came back with another dessert and he still wasn’t happy. This was causing quite the scene and immediately I turned sober to his obnoxious ways. I asked the waiter for the bill and expecting to halve it, this guy pulled the “I forgot my wallet” act on me! I then had to pay $250 dollars without causing more of a scene.
The waiters and staff were clearly appalled at my date as they gave me a slight discount. This was one Tinder hook-up I don’t want to remember.
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Emmy is the founder and content writer at woopdedo. With a background in the performing arts, she then had a career working on cruise ships, until she decided to return to NZ where she spends most of her time storytelling and freelance writing. You can contact her on the social media links below or visit the work with us page.
