10 People Share Dating Stories That Went Embarrassingly Wrong

Dating can be a thrilling adventure, but sometimes things can take a hilariously awkward turn. In this article, 10 people share their most embarrassing dating stories that can make you laugh and cry at the same time.

1.

He ran into Walgreens and asked to put his bag in my purse. I assumed he bought candy. At the movies, right after the opening previews started, he pulls out a brand-new hairbrush, rips the packaging off, does the fake yawn to put his arm around me while holding the brush and starts brushing my hair.

I was shocked that it was happening and didn’t know what to do. He then leans his head on my shoulder while still brushing my hair and starts smelling my hair.

Unknown author / Reddit

2.

We were at a coffee shop attached to a bookstore. He asks me if I like Lord of the Rings. I say, “Yeah, like it. My favorite movie is the first one. The other two got a bit repetitive with the battles.” He’s silent for a moment. “Lord of the Rings are my favorite movies ever. And the books as well.”

“I read the books too,” I reply conversationally. “They weren’t bad, but not my favorites.” He’s silent again. “Lord of the Rings is very important to me.” I’m a little confused now, “I like them, they’re just not my all-time favorite thing, you know?”

Another long pause. His stare is oddly intense, “Lord of the Rings is very important to me, and it’s very important to me that you like it too.” “Well, you know,” I say slowly, a bit cautious, “We don’t have to have exactly matching interests to be compatible. And I do like Lord of the Rings, I’m just not super passionate about it.”

That strangely cutting stare intensifies, “... It’s REALLY important to me that you like Lord of the Rings.” I simply shrugged and resumed browsing, but I wrapped that date up fast and lost his number. Luckily, my lack of intense passion for LotR was enough of a turnoff that he didn’t try for a second date.

in_the_aether / Reddit

3.

Talking to this beautiful girl, we just connected, then we made a plan to meet at a local pub. Show up and turns out it was my younger sister.

Iranisforlovers / Reddit

4.

I had a blind date with Julie. She gave me horrible directions to where she lived, and I almost bailed after driving around for 45 minutes. Eventually I did find her dorm. The date itself was okay, but I knew it wasn’t going to go further than that. At the end, I went in for a hug, and ended up with a handshake.

As I was driving home, my front tire had a major blow up, and I ended up skidding all over the road on what is usually a very busy highway. I didn’t hit anyone, but my tire was shredded all over the road and I had rim damage.

I ended up having to wait until 3 in the morning at a strip mall for a tow to pick me up. I told her about that the next day, and she said she had a jealous ex that punctured people’s tires.

Unknown author / Reddit

5.

My friend’s sister was mid-20’s and getting serious with a guy. He told her there was something important he needed to share. She’s thinking he wants to move in or pop the question. She goes over to his place, and he shows her his secret room.

It was a walk-in closet, and he had it set up with a huge replica of smurf village and liked to play there in his free time more than hanging out with friends. Acting out story lines with his smurfs and pretending he was one too. It was a big part of his life and he hoped she was as into it as he was. She was not.

horsecalledwar / Reddit

6.

Met this guy on Tinder, he was actually really interesting for once, and we chatted for weeks. We arranged a date and met up, conversations flowing, fantastic banter, everything is going great, he walks me home, we make out for a while, and he says he’s looking forward to another date and so am I.

When I get home, he’s added me on Facebook and I see he’s been in a committed relationship for 4 years. I still see him and his girlfriend around Uni. They look super happy.

PonsonbyTaniwha / Reddit

7.

We went out to a nice restaurant, had a nice dinner and everything was good. The check came, I paid with my debit card. It was declined. The credit card was sitting on a desk at home. Checkbook? At home too. Cash? Who carries cash?

After sheepishly explaining the situation and promising to pay her back ASAP, she paid. Walked out to the car and found no car. I discovered it was towed. Took a cab to the towing yard. No money, she had to pay for a cab.

Got into an argument with ignorant tow truck guys who refused to release my car even though it was parked properly, and we had restaurant receipts to prove it, etc. $125. She had to pay. Worst date ever for me.

beyerch / Reddit

8.

My friend took this girl out to The Cheesecake Factory as an 8th grader. They sat down, and when the waiter came over, he just asked for water, nothing else, and wouldn’t let his date order anything. She was pissed, and confused to say the least.

The waiter brought their water, and my friend sent him on his way. My friend takes the water, dumps it on his date, and says, “I just watered a beautiful flower.” The girl walked out right there. He really thought it was romantic. He was crying about it at a party I had later that night.

FantasticCynic / Reddit

9.

He stuck his fingers in my dessert, licked his fingers and did it again! I ordered a lemon meringue pie and offered him to some, he said “no” only to then proceed to say “actually that looks good” and stick his fingers in for a taste. Yuck.

lilbebele / Reddit

10.

I matched with a guy on Tinder, and he offered to take me out to dinner. We were driving, and he asked me where I wanted to go. I told him I was fine with anything. He said, “Okay,” and pulled into Subway. He told me that he wasn’t hungry, but that I should eat! So he stood outside of the Subway and watched while I went in and got myself food.

I was already mentally done, but I wanted to see how much worse it would get. I’m sitting in the car with the sub on my lap, and he decided that it was a great idea to drive around through a dark, isolated ravine that was nearby. He drove for about 10 minutes into the ravine, parked the car next to an abandoned tennis court and said, “Okay, you can eat now.”

I choked down the soggy sub while he stared at me. The second I was done, he pulled the car out and drove me back home. I was grateful to make it home, and it took me several days to process the entire date.

bi_ochemist / Reddit

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