Dating Disasters

23 Real-Life Dating Disasters That Will Make You Cringe

Dating disasters, found on AskReddit.

1. She bought me chocolate, then broke up with me, then ate my chocolate.

My girlfriend of 8 months bought me chocolate, then broke up with me, then proceeded to cry on my shoulder about family problems, then ate my chocolate.

2. She asked if my parents were disappointed in me.

It lasted an hour, but was done forty minutes in when she asked if my parents were disappointed in me.

3. She brought her ex-boyfriend with her.

Met a girl at a bar for drinks, she brought her ex-boyfriend. I noped out pretty quick.

4. It took him 15 minutes before we were “in a relationship.”

One guy took pics with his phone, us, me, of us sitting in the coffee shop, and posted on Facebook “in a relationship” and posts of “my woman” with hearts and “found the one.” We’d met for the first time 15 minutes prior. 15. Minutes….

5. She let me buy her dinner and drinks before making me drive her home so she could fuck some other guy.

Went on a date once with a girl who ordered enough food at the restaurant I took her to load up a nice size take-home box, then got some nice drinks on my dime at the bar. About midnight she informs me that she needs me to get her home because she’s got a date with the guy she’s fucking that night.

6. She had a machete in her purse.

About 20 minutes into the date she pulled a 15-inch machete out of her handbag, declaring with a friendly smile that she had brought it along in case I was a psycho, but she was really happy I wasn’t.

7. But did you make out during the movie?

It was 1993, and a first date with this girl I had liked for about 4 years. We go to see Schindler’s List. Turned out to also be the last date.

8. Her husband…had…died…two days ago.

I went on a date with a gal who was so beautiful that I felt she was out of my league. She was also very friendly and warm and funny. Except, through dinner she wouldn’t let me ask her any questions. She just wanted to talk about me. It was sweet at first but then it just got strange. Finally I refused to answer another until she told me something about herself. She stared at me for a long time and finally said, “OK. My husband…Died…Two days ago.” I was so surprised that I had an anxiety attack. The date was over for a number of reasons.

9. Worst Halloween ever.

It was Halloween about two years ago. Halloween is my favorite day of the year and everyone around me knows that. My boyfriend at the time said he wanted to “do something special” for me for Halloween. Turns out it was going around his neighborhood to go trick-or-treating, which I was okay with, until the girl he was cheating on me with showed up to join us. He invited her. The rest of the night consisted of me crying and her telling me all of the things he said behind my back. Needless to say, I wound up walking home alone (a good hour walk) on Halloween, makeup running down my face from crying, and a new single relationship status.

10. He told me I was walking “like a dog that someone had put socks on.”

I had recently gone through a pretty horrible breakup and was filling my time with lectures and gallery openings. I ended up going to what I thought was a networking conversation but ended up being some kind of date thing.

I had a presentation at work that day so was fairly dressed up but my usual look was toned down. The first thing this guy said was, “You’re wearing less eyeliner than last time I saw you. Good.” I was too awkward to leave right then and there, so we started walking to dinner. He then informed me that “I shouldn’t have worn heels” for him because I was walking “like a dog that someone had put socks on.”

11. He lived with his mom while he was “gathering his thoughts.”

I agreed to go out on a date with a somewhat older guy (I was 18 he was 24). I thought, older guy, what could go wrong? Well, I should have known from the moment he asked me to meet him at his house. I get there, and he introduces me to his mother, and says he lives with her while he is “gathering his thoughts.” He casually mentions that he is broke, out of gas, and lost his job a year ago. So his idea of a date was borrowing his mother’s car, stealing her Krispy Kreme coupons for free donuts, and then walking around a sketchy park. Kept hinting I should pay for the gas for the trip to Krispy Kreme. And then he invited me to his basement to watch TV. I faked that I had to go home to study for an exam and sped out of his neighborhood. He kept bugging me for weeks afterwards, calling me a selfish bitch, and messaging my friends telling them that they were as well. Like, what the fuck?

12. It’s hard (and sometimes scary) to be a woman in the dating world.

Our date was normal…but I wasn’t sure if we going to see each other again.

At the end of the date, he’s dropping me off. He locks the doors (still in the car) and screams at me at the top of his lungs: “I WANNA EAT THAT FUCKING PUSSY! LET ME EAT THAT FUCKING PUSSY!” …

It’s hard (and sometimes scary) to be a woman in the dating world.

13. He was a former Elvis impersonator who draws cartoons of cats puking.

This was my first date after ending a 9-year relationship. Met the guy at a farmer’s market and he asks me to dinner later that week. He seemed a little nervous, kind of weird, but I had no idea. He starts telling me how he is a failed Elvis impersonator and how I should look him up, that he abandoned his 4 kids back in Utah with their mom, he just found out his girlfriend cheated on him the previous month, and that he draws comics of cats puking—would I like to see over our appetizers? I ordered another drink, barely touched my salad, and gave him an awkward hug at the end…..

14. He ordered two double cheeseburgers, two fries, and two shakes—then ate it all in front of me.

This one was so—so bad that I went into denial afterwards and refused to say it was a date.

Guy who is a friend asks me out. I’m newly single and fine with it. He’s sort of a giant fat slob, but he’s funny, so okay. He picks me up on his motorcycle. I’m okay with that. I have to bring my own helmet. He tells me he needs to sit really far back, so I get about 3 inches of seat to try to hang onto, and he says I have to hang on tight. Well, he hasn’t showered, and I can see his dirty underwear and the crack of his butt…I wasn’t about to hang onto anything within reach, but I managed to stay on.

He drives up and down the main street downtown, sort of hot rodding, trying to scare me. Asshole.

Then he takes me to a little burger joint. We go in, he walks up and orders “Two double meat double cheeseburgers, two fries, and two shakes”—I didn’t really want that much food, but okay. I’ve never had a guy order for me before. We go and sit down to wait for the food, and when he brings it back he proceeds to sit and EAT IT ALL. He looks at me and says, “Why didn’t you order anything?”. Um.

Here is the real kicker though: Weeks later I found out from friends that he had been bragging to his buddies (including mutual friends) that he decided not to date me because he used the downtown windows to check out how I looked on the back of his motorcycle, and he decided I was too fat.

What a relief. Yeah. GIANT asshole.

15. He expected a blowjob because he bought me dinner and took me to a movie.

I went out for dinner and a movie with a guy. At both places, I offered to pay multiple times and he insisted that he get it. At the end of the night we’re sitting in the parking lot in his car, he pulls his dick out and asks for a BJ, saying “I mean, I bought you dinner and took you to a movie, it’s the least you can do.”

16. He was a bear-killing bowler who had a restraining order filed against him.

I went on my first date with a guy on my high school bowling team. I wasn’t really interested, but he asked, and I was too awkward to tactfully say no.

After I told him that I was a vegetarian, he proudly showed me a picture of himself with a dead bear he’d shot. When he walked me home, he stopped three blocks from my house and said he couldn’t go any farther because someone in the area had a restraining order against him. Needless to say, I quit the bowling team and avoided him like the plague.

17. He made me pay for my own McDonald’s fish sandwich.

A cute guy asked me out, and so I went with him. He worked at McDonald’s, so he asked me if I wanted to go there. I said okay, although I’m a pescetarian and he knows it, I figured I could choke down a fish sandwich for a cute guy.

Anyway, we get there and my mom had given me three dollars saying,”He should pay for you, but in case he doesn’t, this should cover the fish sandwich.”

So I go in carrying my three dollars and he pulls a ten-dollar bill (yes, you read that right, a ten dollar bill) from the ATM and we order. I only order the sandwich, he orders a huge meal. It comes to 2.45, and he takes my three dollars because he ‘didn’t want to break his ten’. We go back to his place and we sit there eating with his family wandering around, and I dive into my disgusting fast food. I eat most of it, and we go into his room. We’re cuddling and he reveals to me that he is, in fact, a character out of Dragon Ball Z. He also reveals to me that his dad is a pastor and anybody who believes in Halloween is evil.

I left shortly after.

This guy wasn’t fat or neckbeardy in the slightest. He was attractive and fit, and nothing about my interactions with him would have led me to believe this would happen.


I met this guy through some friends. He was in the Navy, so I figured he could be disciplined and responsible. We chatted a lot on Facebook before actually meeting, because he was always out on the sea. One day we decided to finally meet and go on a date to the mall and movies. When I saw him he looked normal just like on his pictures. He saw me and approached to hug me and after he did, he licked my face. GROSS. I didn’t know what to do… Then we walked across the mall trying to hold a conversation and he started playing with my hair saying how white people have very thin hair. (Note I’m Hispanic, he’s Caucasian) I felt very uncomfortable because he was telling me how he almost killed a Hispanic drug dealer (something I didn’t believe of course); not only that but he said he loved me already and that was just super creepy. I just wanted to leave so I pretended I got a text and that I had to leave immediately.

As soon as I said that I had to find the words, right words to say goodbye forever, and when he knew where I was going to with my words he started yelling, yelling in the middle of the mall… “NOBODY FRIEND ZONES ME B*TCH” “I FRIEND ZONE YOU” “NOBODY WILL EVER LOVE YOU”

And I just ran away as everybody looked at me. So embarrassing…months later thanks to some friends I found out the dude was married ever since we first met lol

19. “Well, maybe it’s because you’re an asshole.”

Second date with this girl in SF. After sushi, we meet up with her friends. One of them just knows it all, putting everyone down, giving the waitress at the bar shit. And then she is complaining how hard it is to date. Well I had had it, so I said, “Well, maybe it’s because you’re an asshole.” She stared at me and then threw her martini drink AND GLASS at my face. And then they stormed out. The waitress was standing there the whole time. Brought me a towel and said “Drinks on the house rest of the night.” So I had that going for me, which is nice.

20. Worst breath ever.

This happened about a year back, when Tinder was all the rage at the place where I live.

So I went out on a date with this cute girl, we decide to meet for coffee and everything went by amazingly, she was funny & charming. A few hours went by while we talked. Everything seemed to be going pretty smoothly. Then we decide to go for a ride after the coffee, since it was bit chilly had to roll up the car windows.

A few minutes into the car, the two of us are talking, she’s raving on about one of her friends. And, then this weird smell starts filling up the car (it was somewhat similar to the concoction used to create the powerpuff girls but instead of ‘sugar, spice and everything nice’ this was “rotten fish and anything that died”).

I soon realized that her mouth is the source of that godawful smell. Now, I just couldn’t tell her that she smelled, so I opened the windows. It was extremely chilly (a fresh chilly breeze came in and took some of the smell away), but she got me to roll ’em back up.

Then again after a few minutes the smell of her breath took over the car like a mist that just fuckin’ covers everything and devours anything that comes in its way. (If I had to give her breath a color it’d be one of those dark green ones that they show in low budget horror movies.) I have a dog, and my dog’s breath would be the smell of a magnolia tree compared to hers !

So then I offer her cigarette, (by offering I mean, I practically begged her to smoke in the car, which in hindsight was a bad idea, cause now, I was in a car filled with smoke and bad breath).

Also, now her blabbering, which I had found cute until a few minutes ago at the cafe was a source of grief. Cause every time she’d open her mouth to talk or laugh, all I could visualize was more of that heinous smell escaping out of that Mountain of Doom mouth of hers and filling the space between us.

So after 20 odd minutes, I decide I can’t take it anymore, and ask her where she wants me to drop her off. She gives me the directions and we end up in a secluded parking spot. I knew what was gonna happen next, and the thought of kissing her just made me puke in my own mouth. A part of me was just screaming “Fuck”, “Fuck”, “Fuck”, and thinking, please god save me from this, I’ll be a better human being from now on.

So, she leans in to kiss, I just put my elbow on the car horn while leaning in, there was a loud “honk,” she got a bit startled, the parking lot attendant started walking towards the car. This was my chance to get out, I told her goodbye and just got my ass out of there as soon as I could.

Tldr; Date’s breath smelled like an open sewer pipe.

21. He shoplifted a belt while we waited for our restaurant table.

While waiting for our table, we popped into a men’s clothing store then when we headed back to the restaurant and on the way he showed me the belt he just shoplifted.

22. She just got out of prison for manslaughter.

Met a girl on Tinder and we decide to go to brunch. She was really weird about not drinking a single drop if she was driving. But if I drove, she’d love to get bottomless mimosas. Figuring that might get me laid, I didn’t notice the red flag. About 15 minutes after we sat down, she proceeds to tell me how she just got out of prison for manslaughter involving a DUI. That kind of killed the mood.

23. He was out of prison for murder.

We met online. He seemed like a nice guy, good job, great conversation, lots in common. Then, just as dessert arrives, he breaks out the old “so, I should probably tell you something. I’ve been to prison. For murder.”

Full credit to him for being upfront. He gave me the details so I could go and check it out online, etc. He seemed pretty genuine about everything, his story matched up, etc. After some thought, decided maybe friendship and see what would happen. Then he just sort of vanished one day. A few weeks later I saw him wanted for skipping bail on the national TV program for wanted people. Thought Catalog Logo Mark