10 Stories Where Dating Took an Unexpectedly Embarrassing Turn

Dating is full of surprises, but not all of them are the good kind. Sometimes, the most romantic plans go hilariously wrong, leaving us with stories we can’t believe happened. These 10 stories of dating gone wrong will have you cringing, laughing, and maybe even feeling a little better about your awkward moments.

1.

I was using a dating website to find a match. I connected with a girl who had no picture, she said she was slightly older than me. I responded I was into mature women. My picture was in a dimly lit room which didn’t reveal much. Turns out that was my mother. This is not a situation we look back and laugh at.

Unknown author / Reddit

2.

Met a lovely girl over Tinder, we hit it off and had a great conversation, decided to meet in person for coffee the next day. She showed up on time, looked just like her pictures, and brought her boyfriend.

Unknown author / Reddit

3.

I went on a date with an older coworker from my first job at a supermarket, I was 20 he was 27. He took me to lunch and didn’t let me order for myself; when the waitress came to ask what I wanted to drink he cut me off and placed both my drink and food order.

He said I needed to meet his mom and brother soon and how we should get married and eventually have kids. He didn’t know a single thing about me. I quit shortly after that and he’d message me on social media now and then saying things like my then-boyfriend didn’t deserve me until I blocked him everywhere.

BeeRivers / Reddit

4.

She wanted to have a picnic. I spent an hour getting this table nicely set up with food, dessert, candles, a tablecloth, and cushions for us to sit on comfortably. I’d never done this, but was trying hard to impress.

She arrived late, there was no connection hardly at all, she wasn’t talkative, she said she loved Latin/Caribbean food, so I got take out from one of the best places, she didn’t touch any of it.

I asked her a couple of times if she was ok and she’d just smile and say no. I sat through this for almost an hour. Finally, I asked her what was wrong. She responds, “Nothing really, I just think this is all a bit overboard for a first date, it’s kind of cringe like you’re desperate.”

I just bit my tongue and said, “If you’re not going to eat, I sure am!” There was a couple sitting on a swing near us and I went, “Hey guys! You hungry?” They were on a date but were broke, so I invited them over to enjoy the table full of food with me.

She left a few minutes after they came over. I had the best time with these two strangers, eating and laughing and telling them what happened and both of them telling me I deserved better. I’m still good friends with them some 10 years later now.

MonkeyManJohannon / Reddit

5.

I went with a girl to see a late-night show. The public transit stopped running, and we didn’t have money for a taxi, so we walked to her house since I lived much further. We collapsed fully clothed on her bed and fell asleep. 3 hours later her dad shook me awake and demanded to know who I was, then when he found out I was studying chemistry in college he started questioning me about thermodynamics, which was not my strongest subject.

ThadisJones / Reddit

6.

He got mad at someone and ripped off his shirt. Not like he took it off abruptly. He freaking grabs the middle of his shirt with two claw hands and tears it off his body screaming. I was stunned. Never in my life could I have even imagined I would see that and be on a date with that.

Unknown author / Reddit

7.

Went out with a girl I met on a dating site. We met for coffee, got our drinks, sat down, and she forgot how to talk. For almost an hour, I’d try to start a conversation and bring up any topics I could think of. I tried talking about our jobs, hobbies, families, anything. Her responses were just “Uh huh”, Oh yeah“, “That’s cool” and “Nice.”

She wasn’t looking at her cell phone, looking out the window, or being distracted. Completely forgot how to have a conversation while staring at me for the hour we were at the coffee shop. It was the shortest and longest date I’ve ever experienced. After leaving, I hit the McDonalds drive-thru and had a consolation meal to put that bad date behind me.

Unknown author / Reddit

8.

I once had a first (and last) date with this guy who tried to get me to dictate his every move. Like he wouldn’t turn left or right unless I told him to. I just said, “Yeah I’m not doing that” and sat down on a bench while he continuously walked into a wall.

my_name_is_not_theo / Reddit

9.

I had a guy I was just starting to see over to my “place” (dorm room) to watch a movie. He started telling me about how he works for his dad in the summers, and his family owns the company. He decided to show me his family’s company website, and when he started typing the address in, it popped up automatically.

I’d been googling him and knew all about it (the whole time he was telling me his story, I was pretending I knew nothing). He just said, “Uh...that’s...weird”. I said, “Uh..yeah...”. Awkward silence for a couple of minutes. It didn’t work out, and I haven’t seen that guy in years, but it’s one of those stories where I still cringe every time I think about it.

Unknown author / Reddit

10.

She showed up with 4 girlfriends who all began to order the most expensive stuff they could. She told them I was paying. I slipped out after saying I was going to the restroom. Silenced the phone, but very much enjoyed reading the 70+ angry texts over the next few hours.

ImprovementFar5054 / Reddit

Sometimes, life delivers twists so unexpected they feel straight out of a sitcom. In this article, we found 10 stories that prove that the funniest, most surprising moments aren’t planned, they just happen. They show how real life can outshine fiction, reminding us to laugh at the unexpected and find humor in the everyday chaos.