People Share Their Absolute Worst Dating Horror Story


Dating is, in theory, your chance to get to know someone and decide if you want to pursue a relationship with them. Sometimes it takes a few dates to figure out what the potential for things are. Sometimes you don't even have to make it all the way through a first date before you can 100% scratch things.

One Reddit user asked:

What is the story of your worst date?

And from there we get this article - a celebration of bad like you wouldn't believe. We've got stealing food from the homeless, we've got drunken heckling, we've even got a date that happened but didn't happen thanks to a dentist and some drugs.

Brace yourself, we're boarding the Hot Mess Express and the first stop involves a dude with no pants.

The Pants Dance

He took off his pants

After a first date of dinner and a movie he asked if I'd like to "have some fun." I said No. He apologized for overstepping himself

I told him "hey, I totally understand and it's okay!"

Now the confusing part...he took my word "okay" as consent for "I totally want to do sex now" so he immediately and quickly took off his pants again.

Such awkwardness when I explained it was still a no.

- cooldart61

Same Address

Disgusted Cringe GIF Giphy

I went out one night with some of my girl friends. I was the young, naive girl in our group. We went to this bar that is on a lake and had a great time drinking margaritas. I met a guy...we danced, laughed...really clicked! My girl friends were ready to go...I didn't want to. He was making promises that he could get me home, but the DD in our group put her foot down and said we had to go. We exchanged numbers and made promises to talk soon, and the DD took us girls home.

The next day, I get a text from him! I'm so excited because he had to be interested if he texts the next day right?! We make plans for dinner and he offers to pick me up.

Him: "So, pick you up at the same address?"

Me: "Same address? What are you talking about."

Him: "The house I dropped you off at."

Me: "You didn't drop me off?"

Him: "Shut up. We had sex in your drive way."

Me: ", we did not."

Him: "Yes, we did!"

Me: "I'm really confused. And I think you are too...but I'm not the girl you went home with last night."

So the date died before it ever got started. He quickly realized the mix up...tried to back track by laughing, "Haha! I was just kidding about the sex..." It was horribly awkward and cringeworthy. This part was actually a phone call (way back in the early 2000s). I mumbled something about having to go and hung up. He didn't try to call back or anything.

Grateful for the DD though!! She was a lifesaver.

- Cozy_caterpillar


I had been seeing this guy for a few months but he kept me on the down low/didn't want to commit. Finally took me out to dinner in public we sat at the bar. A little after we ordered his two friends got to the bar and he immediately got up before they spotted us.

He went over to them and sat and ate dinner with them and texted me not to come over. SO I sat alone for most of the night until his friends left.

- uninhibitedrnr

Failed Tests

I had an old college friend come to visit me and stay for a weekend. Knew her in college. She was amazingly intelligent and fascinating, but we were both spoken for at the time. Years later I got Facebook and she was one of the first people to find me.

Both of us were single. She asked if I wanted to date her. I said hell yes! I was thrilled at the prospect.

The weekend was spent listening to her narcissistic BS

She told me jokes that are as old as the internet, reworded to sound like personal life anecdotes

She told me all this insane edgelord sh!t she used to or still does, like taunting police (back in 2009) or sneaking Cuban products back to America when the embargo was still in place.

She tried to start a fight with a bouncer when we went to a bar and she forgot her ID back at my house (a block away.)

We visited some of my best friends, and the moment we parted she talked sh!t about them non-stop.

My brother came by since I texted him I was out and hung out. She talked to him for quite a while. He left, then she spent the rest of the night talking about how attractive he was. At this point I was just counting the hours until she left. I was no longer interested in her.

She FINALLY left, and I get a text that night:

"You failed all my tests. You laughed at my jokes that weren't really jokes, You didn't defend me against the bouncer, and you aren't interested in my passion (fighting bouncers and cops) and you sat there and took it while I talked about your brother. Also, I don't find you physically attractive."

I didn't reply. I just cut my losses and fell asleep.

Several months later at 4 am I get another text from her. Same text as I just wrote, only this was out of nowhere and the injury following insult. I gave her absolute hell for it, and blocked her on Facebook.

She then made duplicate Facebook accounts, and threatened me on those too. She gave up eventually, but I dodged a fcking bullet.

- RadleyCunningham

Pay Attention

My freshman year of undergrad my Teacher's Assistant for a comp sci class I was taking asked me on a date. My university allowed upperclassmen to TA in intro classes. This guy was a senior but unbeknownst to me was actually 27 cause army. He seemed normal/nice enough, so I agreed and we went to dinner at a random restaurant in the city. He ordered for me which was not my favorite but I was like whatever cause he seemed to know the place really well.

He was a narcissistic weirdo and he talked about himself the entire time and kept asking me/telling me to "pay attention." He told me all about his ex fiancé and basically went on a rant about how white women are so entitled so now he's only interested in "black queens." He was white.

It was making my skin crawl, I felt physically ill. At the end I wanted to split the bill he said he would pay since I'd be paying him later wink wink. I didn't even know what to say or do I just stared at him and excused myself to go to the bathroom and I left through a side door. Luckily there was only two weeks left in the semester so I only saw him again for the final.

- mandysworldxxx

Brick Wall

From the get-go, talking to her was honestly like talking to a brick wall. If I asked her a question, her reply was typically one word or at most a single sentence. And no questions in return or any effort to keep the conversation going.

At one point, she got up to go to the toilet, and the older woman who was sitting at the table next to us leaned over and whispered to me "I have to say, I really admire your patience. She is a nightmare!"

- RedWestern

Won't Be Trying Again

Went out with guy from work who I didn't know much about. He turned out to be a d!ck in many ways and was drunk when I showed up.

Lowlight of the night was when he started douchily heckling the small cover band that was playing in the bar. The guy on the mic said, "I'll give you 10 dollars out of my own pocket if you can tell me this girl's name" and you guessed it; he literally blanked on my name in front of a room full of people.

The next day he texted me saying, "You can try again," as if I was the one who blew it.

- buttproblemzthrow

The Doggy Deal-Breaker

Met a guy at a professional night out; he seemed interesting. He invited me out for Chinese food and a movie, but insisted I come by his house first to meet his four dogs, because not liking his dogs would be a deal-breaker. Cool, I love dogs!

I follow directions to his house, which is a mobile home with a small fenced yard. So the dogs must be little, I think. No. Four large, mannerless dogs living inside this mobile home and the smell is completely encompassing.

Turns out "dinner and a movie" meant watching one of the thousands of VHS tapes and DVDs he owned while he tried to get the clothes off me, while four big dogs bounced around. I declined his kind offer of incredible sex and got out of there. My clothes went directly in the washer and my car smelled like dog for days.

- Flahdagal

The Dentist

I hate the dentist! Giphy

I got a girls number and went to the dentist a few days later. 4 wisdom teeth and a lot of drugs later, I apparently showed the dentist her number as my emergency pickup.

I have no memory of these events, but apparently she picked me up, took me to the pharmacy for my medication, and dropped me off at my apartment, where I passed out.

That was our first and only date. Apparently I didn't make a good impression. Can't blame her for that.

I have no idea why the dentist office asked drugged-up me for a pickup number. I assume they couldn't reach my primary help number, but I never asked.

- TedW

Subway And Stale Donuts

I matched with this guy on tinder, and he offered to take me out to dinner. I thought that sounded nice so later that night he picked me up. We were driving and he asked me where I wanted to go.

I told him I was fine with anything. He said, "Okay then" and pulled into Subway. He then 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.

At this point I was already mentally done but I wanted to see how much worse it would get. Spoiler, it got so much worse.

So I'm sitting in the car with the stupid sub on my lap, and he decided that it was a great idea to drive around, specifically 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 was just thinking, "I really don't want to die here", so 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 so grateful to make it home in one piece that it took me several days to process how screwed up the entire date was.

The cherry on top: at 2am that night, he came back to my house uninvited, carrying a bag full of stale donuts. He asked me if I wanted to have sex (but it had to be without a condom since he didn't have any.)

- bi_ochemist

39 Minutes Too Long

Met at a coffee shop... Within 15 minutes I was trying to figure out how long I had to stay to be polite....

  • He believed he was an alien
  • Told me about how he has died twice
  • Even though he knew my ex abandoned my daughter, proceeded to be proud about how passive aggressive he was with his own kids, such as refusing to see them if they didn't want to do exactly what he wanted....

Noped outta there after about 40 minutes... 39 minutes too long....

- RazPi34

Biology And High Fives

I was 28 or 29 years old at the time. We'd been talking for approximately 10 minutes over one drink...

Him: So do you want kids? Cuz if you do, you don't want to wait too long. You're drying up.
Me: ...
Him: It's biology. Don't be mad.

Then there was the time I met a guy for coffee, it was like 9 or 10am. The coffee shop was busy but fairly quiet. He'd ask me a question, I'd answer and he'd loudly exclaim "Nice!!! High five!!!!" He did this like 4 or 5 times before I had to tell him to stop, I didn't want to keep high fiving...

- CaliAvi8rix

Taking Food From The Homeless

He said he was taking me out to dinner. He took me to a homeless shelter to eat. I felt so guilty.

He was not homeless and not that poor. If he couldn't afford to buy me dinner or anything we could have just hung out at a park or I could've bought us dinner; I lived in my parents at the time and didn't have to worry about food at all.

I was shocked, I didn't know what to do. I felt so guilty taking that food from people who needed it but I didn't wanna make a scene or be rude to my date, I didn't know him well enough to know that he didn't need help with food. I found out soon enough he was just a d!ck taking advantage of charity... amongst other things.

He gave me some tea and it tasted terrible and then told me that it was magic mushroom tea. Dude tried to drug me.

- the8thloser

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