Dates From HELL: 25 Women Share Their Cringeworthy Tales

lookcatalog / Illustration by Daniella Urdinlaiz.
lookcatalog / Illustration by Daniella Urdinlaiz.

1. He cried a little bit when I beat him at chess.

“I met up with this guy from the internet at a bar with board games. He wanted to play chess, but I don’t play chess, so he offered to teach me. I learned from magazines that boys feel manly when they teach you things so I was like, sure, why not. Well, I’m a quick study, and I ended up winning the second game. He got so upset that he cried a little bit. We did not checkmate.”

–Madelyn


2. He left me alone in the dark while he jerked off in the woods.

“I met a guy a bar who told me he ‘owned his own business’ which turned out to mean he drove a bike taxi. We met to see The Breakfast Club in Central Park, and he said I should ride in his bike taxi to ‘save time.’ I told him, ‘The only way I’m riding in your bike taxi is if you’re carrying my dead body to the morgue,’ so I walked next to him as he rode slowly. After watching The Breakfast Club, he showed me a romantic, secluded section of woods in the park. We made out there for a short time, but it was dark and I started getting creeped out. When I told him I wanted to leave, he said, ‘Hold on, I need to take care of something.’ Then he left me alone, in the dark, sitting on a rock in the woods while he disappeared to go jerk off. He didn’t seem to think he’d done anything wrong. I gave him one-word answers as we walked back to the main drag of Central Park. He got zero more dates.”

—Ashley


3. His angry wife showed up with him.

“I reluctantly agreed to go on a date with a man who was separated, and who said his divorce was going to be finalized soon. He said he and his soon-to-be ex were on good terms for the children’s sake. Lies! While we were leaving dinner a car drove up, and out popped a woman who seemed ready to punch me down. He started to tremble, as she was bigger than he was. She came charging towards us, and I didn’t wait to hear the end of it, I just hightailed it out of there. He called me days later to offer an explanation, but I just hung up on him. Any woman with that kind of anger obviously has unresolved marital issues.”

—Julie


4. He told me he had a really small penis right before we had sex.

“My worst experience on a date was, when the end of the night came and I asked my guy if he wanted to come in for awhile and he agreed. We started to make out and when things got all hot and heavy, and we were about to have sex he pops out with, “I am half Filipino, so I am really small! I hope this does not matter and I hope you can feel at least something!” That was a complete turn off and I told him this, and that I no longer was in the mood to have sex. And that all of a sudden I felt really tired and that he should leave. I felt bad about it, but God that is not something you tell someone when you are about to have sex!!!!!”

—Jess


5. He told me that everyone hated him and that ever girl he ever dated was a bitch.

“Rejection Guy told me within the first 20 minutes of meeting him that he had been fired from almost every job he’d ever had because his bosses hated him, his roommate hates him, and every girl he’d ever dated was a witch with a “B.” Yes, he actually used that term. Over dinner. With a girl. On a first date. Obviously I wasn’t exactly seeing rainbows and shooting stars. More like landfills and litter boxes. It was AWFUL. (Not to mention he ate only the centers out of the bread slices the waiter brought us to share, leaving the rinds, which was just plain weird. And left a trail of crumbs across the table long and thick enough to entice every ant in the middle Tennessee area.)”

—Mandy


6. The most hilarious part was when he pulled out his Trojan Magnum out of his sex kit. Honey, it’s not that big!

“I met this guy for a date at the coffee house. First time I saw him my gosh he looked way different than his picture (it was his real pic though). He just had a different haircut and wore his glasses.

I don’t know why I ended up taking him back to my apt. Horny? I guess so. The sex was horrible!! But the most hilarious part was when he pulled out his Trojan Magnum out of his sex kit. Honey, it’s not that big! He couldn’t operate that thing anyway. It was borderline painful.

Soon enough I escorted him to the door and said goodbye. He emailed me saying the sex was amazing and we should do this again. Not only the sex was horrible and he thought otherwise, but also I was downgraded from a date to a booty call.”

—Perry


7. The guy asked me back for 20 cents that I owed him for lunch.

“The guy asked me back for 20 cents that I owed him for lunch.”

—Mango


8. He TOOK OUT HIS DENTURES while we were eating.

“So I met this guy on Skout dating app. He rides a bike (those scooter kind) and he asked me out for supper. So I was like okay let’s go. And he really came to meet me. But I refused to sit on his bike cus he brought a REAL OLD HELMET. So we walked to the prata shop. He didn’t want to eat, so I ordered roti john. When the roti john arrived and I started eating, he stopped me and asked if he can have a piece. Initally I was like, ‘Wot, okay.’ So he took my knife and fork and cut for himself to eat. I was quite grossed out already. But never mind. He then proceeded to complain about his life and THEN HE TOOK OUT HIS DENTURES and said that he has missing teeth cus of his army experience. Then proceeded to take my knife and fork and cut another piece for himself. I WAS LIKE WHAT THE F***. I WAS SO HORRIFIED and disgusted, I lost my appetite immediately and said I was full and I wanted to walk home. I also deleted the Skout app ’cuz I can’t take that sh*t no more.”

—Clara


9. I texted my friend about what an asshole my date was—but sent it to my date by mistake.

“I was on a blind date with this AWFUL guy. He was rude to the waitress and made comments about my order. I was so ready to go home, so I texted my friend under the table about what an asshole the guy was. Turns out I sent it to him on accident! He saw the text and stormed away from the table as soon as the food arrived. The waitress snuck me out the back door of the restaurant and I never saw the guy again!”

—Kate


10. He broke my computer and told me to sue him, so I did—and won!

“I went on an online date and I happened to have my laptop computer out because I thought he wouldn’t show up. He showed up and immediately spilled hot tea and broke my computer, which ended up costing almost $1,000 to fix. He said he would pay for half, but instead changed his mind and said, ‘If you want my money, sue me.’ So I did. I ended up getting my half.”

—Jennifer


11. He proceeded to lecture me about how careless, cruel, and irresponsible I was.

“After I got out of a long relationship, the first date I went on was with a guy from OK Cupid who was just OK. Since I was still getting my sea legs back, I agreed to a second date. We went out to dinner, and he started saying a bunch of things that were basically planning our upcoming relationship. Worried that he was getting too serious, I mentioned 20 minutes in that I wasn’t ready to be exclusive with anyone yet—something that’s pretty common in today’s dating world, right?

Well, not to him. I should have left then, but I was really hungry, so I sat through dinner while he proceeded to lecture me about how careless, cruel, and irresponsible I was, and how I should think about what I really want before I go on more dates and lead more guys on like that. Not only that, but he then called me every two weeks for the next two months, asking each time if I was ready to be exclusive yet.”

—Meg


12. Right before we were about to have sex, he went into diabetic shock.

“Right before we were about to have sex, he went into diabetic shock. We spent the night in the ER. I’m obviously relieved he was OK, but what a date.”

—Ashlee


13. I got a call from a cop asking me to pick the guy up because his license was expired.

“He texted me that he’d be late. Then he said he had to change a tire. Then he got pulled over for a taillight that was out. Then I got a call from a cop asking me to pick the guy up because his license was expired. Ugh.”

—Cait


14. We went on a triple date…with his charmingly Botoxed mother.

“I was 16 and my boyfriend and I had gone on a triple date…with his charmingly Botoxed mother. He held both of our hands through much of the date. When it came time for all the couples to slow-dance, I sat alone with my thoughts while he danced with his mother. To make up for this Oedipus-like date we were going to go to dinner and a movie, just us. He picked me up and immediately got a phone call from his drug dealer friend who wanted him to join in smoking. They were also smoking cigarettes the whole time, which I’m allergic to. Being the considerate boyfriend he was, he didn’t want me to be sick and instructed me to sit in the car. I waited there for over an hour while they hung out, and by the time they were done we had missed the movie.”

—Aviva


15. He hugged me tighter and started moaning and humping me.

“I met a guy at a coffee shop for a first date. It was awkward and I was not interested in him at all. I went to the bathroom and texted friends to ask if it would be terrible to sneak out the back and leave. They told me to go back, be polite and end it; how bad could it get? I went back to tell him I had to go and he stands to hug me goodbye. I didn’t want to but he wrapped his arms around me and bear hugged me—hard. When he wouldn’t loosen his grip, I yelled for him to let me go and he hugged me tighter and started moaning and humping me. I finally wiggled free and took off running for my car. And, of course, a few days later he texted back asking for a second date. No thank you, creepy coffee-shop humper!”

—Allie


16. I kept staring at his one giant eyelash.

“There wasn’t really anything wrong with the date, apart from the fact that the guy had one really long eyelash. No kidding—it was well over an inch long, and because it was a bright day, it kept glistening in the sun. I couldn’t take my eyes off it the whole time.”

—Allie


17. Halfway through the meal he pulled out a creased photo just of his ex and began to tell me how much he missed her!

“The date was going well…until halfway through the meal he pulled out a creased photo just of his ex and began to tell me how much he missed her!”

—Hollie


18. He puked all over me and then said that I am really caring like his mother.

“We went into a bar and everything seemed all right until he got really nervous and started ordering different kind of drinks and got drunk. I had to call a cab and get him home but as we got out he puked all over me and then said that I am really caring like his mother. That was definitely the cherry on the cake…”

—Alexandra


19. He took another girl home with us, so I slept on his sofa.

“We went to a club where he decided he was no longer interested in me and took another girl home with him. It wouldn’t have been quite so bad if I’d lived locally or knew someone who did but I didn’t…so I had to go back to his and sleep on his sofa whilst the two of them were *ahem* in the bedroom. I snuck out the window the next morning.”

—Emily


20. He brought a backpack full of sex toys.

“I met this guy on (a dating website). We seemed to be getting along great through text and email. We exchanged pictures and we were, like, constantly texting. So, finally I invited him over to my place for the first date—I mean, I thought we knew each other pretty well.

When he got here, he had two backpacks. I was like, what? But I gave him the benefit of the doubt, like, maybe it’s games or I don’t know what. Later, he opened them—one full of clothes and his stuff, and another one full of toys, like sex toys. I was like, ‘Uhhh, where are you going after this?’ I tried to laugh it off. And he was like, ‘What do you mean where am I going? I feel like I’m home.’ He smiled like I was supposed to be all happy.

I went to the bathroom and texted my brother what was up and to come over, and he showed up in like 10 minutes banging on the door all crazy, and I played dumb, like ‘Oh, who’s that?’ He scared him off. No more online dating for me.”

—Daniela


21. His bipolar ex-girlfriend came along with him.

“The gentleman I had been talking to online on (a dating website) was a father of three, divorced. He lived out of the Valley, but worked in the Valley. We made a date to meet for coffee.

At that time, it was a big deal because I put makeup on and did my hair and picked an outfit out, and it was a very big deal to go that extra mile to meet someone in person.

He comes in the door and I recognize him right away from his picture, and behind him stands a girl, like five inches from him, like, from maybe his right shoulder, the entire time that we greet one another. And I said, ‘Hello, how are you?’ And I introduced myself because I had no clue who she was.

The next thing that happened was he looked at me and said, ‘We’re going to need to talk another time.’ And that was it. And he disappeared.

So, I left, and he messaged me maybe the next day saying that that was his ex-girlfriend who had tracked him down. She was bipolar or something, that she was desperate to talk to him. He was like, ‘I know I ruined it.”

—Marilyn


22. His mom told me he was breastfed until he was five.

“One time, I got dropped off at this boy’s house before our date and his mom started telling me weird stuff. Like the fact that he was breastfed until he was 5… Needless to say, we only had one date.”

—Chloe


23. The surprise guest was his cancer-stricken wife.

“My worst date was definitely the first time I met someone who I originally met online. We power-chatted online for months, he mailed me pictures and he looked quite attractive. I was truly looking forward to meeting him, but what a disaster. When I arrived at the restaurant where we were scheduled to meet, he was a full foot shorter than me (when he told me he was 8 inches taller). He was completely bald (unlike his pictures), and was at least 15 years older than in his pictures (which he ‘forgot’ to mention).

What stunned me the most though, was his dialysis machine!!! I have nothing against people with kidney problems, but I think that is something he should have told me! Anyway, being the nice person I am, I sat down to have dinner with him, and tried to be non-confrontational, but let him know I didn’t appreciate his dishonesty.

He apologized and I figured I’d make the best of the date, since he had flown 2000 miles to meet me. But here’s where it gets totally insane. Towards the end of the date, this woman walked up to our table and introduced herself as his wife!!!!!! I nearly choked! She smiled and sat down, and the two of them went on to inform me that SHE is dying of cancer, and wants to find a woman to marry and take care of her husband so she can die in peace!!! She thought I’d be perfect. Needless to say…that put me over the edge. I thanked them for dinner, wished them luck in their search, and left. Maybe it’s mean, but I never talked to him again. YIKES!!! Luckily I was brave enough to agree to meet other guys in the future, and they have all been great! :-)”

—Lisa


24. He started kissing another girl right next to him.

“We were at the theater at that time. I excused myself for a while to go to the ladies room, but when I came back he’s kissing the girl sitting right next to him. What I did is throw a box of popcorn on their heads and told him looooossssseeeerrrrr!!!”

—Leanna


25. He asked for a blowjob on the first date.

“My worst date experience was sitting in a park, doing nothing, and saying nothing, until he asked for a blowjob on the FIRST date!”

—Kayla TC mark

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