The Worst Dating Stories We’ve Ever Heard


Dating can be pretty risky, especially if it’s a blind date. We’ve all have our bad date stories, but some people have one that’s so terrible we honestly cannot believe they happened. Some make great stories down the line to tell a group of friends, while others? Not so much. They leave you wondering how things could go so wrong.

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Ice-Skating Gone Wrong

“Back in college, I was invited to an ice rink with a girl I liked and some of her friends. I did not know how to ice skate, and I did not pick it up very quickly, but I wanted to try and impress her somehow. Well, I hugged the wall the whole time and made a fool of myself. The highlight was when I saw a flash of light as I fell in front of a group of people. Turns out I had fallen right at the moment someone took a picture, so my failure was immortalized forever. She took me back to my apartment and ended the relationship before it began.

“On a lighter note, the woman who is now my wife was at that ice rink on that night. We didn’t realize we were there the same time until a year or two into our relationship and she exclaimed ‘You were that guy who couldn’t ice skate! Yeah, she didn’t seem that into you.’”

Don’t Eat the Soup

“Went on a blind date with a lady who wouldn’t stop picking at her scabs. Just made a pile out of them on the restaurant table. I excused myself to use the washroom and when I came back my soup was there, but the pile of scabs wasn’t. No, I didn’t eat the soup.”

Time to Clean the Walls

“Happened to my cousin. […] She met him at his house. They talked and had a coffee, and he asks what she would like to do. She suggests a movie. He said ok, let’s go to blockbuster. They go to blockbuster (this is where it all starts). They pick their movie and head to the cashier.

“She says she doesn’t feel so good and remembers waking up on the floor. [He] told her she passed out and hit her head pretty hard on the counter. [H]e was begging her to go to the hospital right then and there. She said no I’ll be fine, let’s just go watch the movie. He agrees. They get back to his place. He keeps asking if she’s alright, [and] if she would please change her mind and go to the hospital. She says no over and over. She doesn’t remember falling asleep, but she guessed that’s what happened because suddenly wakes up urgently needing to sh*t and vomit. […] [S]he scrambles to the floor feeling dizzy again, starts crawling (literally) asking where the washroom is. He tries picking her up to take her, but she couldn’t hold back. Throws up all over his floor. All over him. Shi*s in her pants. She starts crying. She said he was so concerned, he didn’t even care he just took her to the bathroom to finish. While they make it to the bathroom, she said she pulls her pants down before she makes it to the toilet and sh*ts like a parrot all over the walls. He gently closes the door, says, ‘pass me your clothes,’ and he has something for her to wear. She agrees and does so. She said she stopped vomiting and sh*tting and finally agreed to go to the hospital. He takes her.

“While she’s telling me this, I am laughing so hard, crying, rubbing her head, and wondering if this is all a joke. No, because they ended up getting married and we bring this up at least once a year.”

“Like a Station Wagon Full of Asthmatic Seals”

“He critiques my driving the whole way [to the restaurant]. ‘Wow, you drive closer to the left than my dad. You’re half in the other lane. Be careful.’ I was nowhere NEAR the other lane. I have never, to this day, and I am now middle-aged, been involved in an accident when I was driving. I’m a very good driver.

“We get to the restaurant. It’s a regular Chinese buffet. One of the dishes is sweet and sour meatballs. The server comes over and asks how our meal is. Ben [her date] laughs – and when he does, he sounds like a station wagon full of asthmatic seals – and says, ‘If I WANTED meatballs I’d have gone to the Italian place across the street!!!’

“He then starts talking about his family. And then crying about his grandmother. Who died when he was 8. And not just ‘Wow this came up, forgive me I’m a little misty-eyed.’ He’s SOBBING.

“Then he starts peppering me with questions, all beginning with ‘if we start dating…’ ‘If you ever stay over know I have a picture of my gma [sic] on my dresser. I won’t take it down, but I will turn it around when we have s*x, like I always do when I mast*rbate. So, you don’t have to worry about that.’

“We get to my place, […] he comes in, calls his dad, and while he’s on the phone my cat comes in the room. I pick him up, kiss him on top of the head, and say I’ll feed him in a minute. Ben says ‘Have any men ever been intimidated by your relationship with your cat? Because that just made me really uncomfortable. I mean you KISSED him and TALKED to him!’

“The friend who set us up never spoke to me again.”

A Stolen Moment

“At the date, she was late, so I started talking with the waiter. […] About 30 minutes late, she arrives, full of apologies. The date went ok, but she was nervous. I blamed it on a 1st date.

“Until the police arrived. Apparently, she was shoplifting at a shop next door, and the camera images showed where she went. Fortunately, the waiter could help me not get arrested.”

Rude and Ignored

“I had met this really attractive Russian girl on, and after talking for a few days, we decided to get dinner. It was just awkward, and she kept on making it purposely more awkward by ignoring me—rolling her eyes and constantly staring around at things. She got really annoyed our food wasn’t coming after about 5 minutes. It was just so bizarre because on the phone we had gotten along pretty great, but she just refused to make small talk during the date. Who does that?”

Tug of War

“Took girl to movies (I now realize not the best location for first dates). She asks, ‘can my best friend come too?’ I say of course you can! (trying to be nice, was also assuming it was going to be a girl).

“Shows up with her friend, who is indeed a guy. This is when I find out that it’s her one-and-only ex, but they remained best friends and nothing is happening between them. Go to pay for our tickets (me and her), even when she offered to pay for hers. After buying, she turns around and buys her ex’s ticket.

“It was like a tug of war for the rest of the night fighting for her attention. Of course, I lose. They are best friends. When I get home the guy adds me on Facebook, and he proceeds to tell me don’t bother trying to date her, she’s a terrible girlfriend. Thanks for the heads up.”

Just Listen, Dude

“Meet a guy from OKCupid. He seems nice, but never stops talking. After interrupting me for the 3rd or 4th time, I finally ask him ‘do you want to hear anything I have to say?’ He apologizes profusely, says ‘you’re right, I’m so sorry!’ and pulls out a pad of paper and a pen. He then jots notes as I’m telling him about myself and whatnot. I finally ask him what he’s doing, and he says ‘oh, I’m writing down things I want to tell you when it’s my turn to talk again.’”

Not a Quid Pro Quo Situation

“I paid him $20 in gas money to come pick me up because I lived fairly far away and figured it was fair. I then paid $45 for dinner plus a $7 tip. Then I bought $25 in shisha to smoke hookah together because he loves it but was out of shisha.

“He then demands s*x […], and I decline because it was a first date. I wasn’t even liking him enough to kiss him. He did this half-cry thing in which no tears came out, but he was ‘sobbing’?

“I ended the date there and asked to be driven home. He said he’d drive me home if I had s*x with him. I ended up taking a […] taxi home. I waited outside his house for two hours late at night waiting for the taxi.”

Cheapest of Cheap Dates

“Blind date. He suggested this swanky French restaurant he said he loved, which thrilled me to my marrow, as I LOVE French food and wine.

“When we got to our table, I picked up the wine list, and he looked at me with this contemptuous look and said, ‘I don’t drink.’ So, feeling judged, I ordered water. He then said we should split an entree ‘because the prices here are ridiculous.’ And I’m thinking, ‘Now wait a minute, YOU picked this place, and you said it was your favorite, meaning you knew d*mn well what the price point was, and if you can’t afford it, why didn’t we go somewhere else instead?’

“Obviously, I was planning on paying half the check. […] [W]e’d even joked about that during a phone call a few days previously, so he KNEW I didn’t expect him to pay for me. […] He told me to pick three things that sounded good, and we’d share one. So, I told him my three choices, and when the server came back, he ordered the cheapest thing on the menu, which was not one of the things I’d selected. We shared our tiny meal and split the check ($12 each). Conversation was stilted and awkward, and he answered all my questions with one-word answers. Eventually, I felt like I was interrogating him, and we just sat there in silence.”

Talk About a Third Wheel

“We were at a Mexican restaurant. Half an hour or so in she invited her roommate to the meal. She showed up, and the two of them talked nonstop to just each other, then asked me to pick up the check for the 3 of us.”

All Girls Like Prince

“When he takes me home, he parks outside of my house and assumes he’s coming in. I’m like…. no? Genuinely confused, he asks why not. He says he did everything right, he bought me dinner and a drink, so he should get to come inside, and we should have s*x now. Because that’s how it goes.

“Then, we start ARGUING about it, and I start to worry that he’s going to just like, enter my apartment whether I like it or not. I am having to literally explain that just because he bought me dinner does not mean I have to f*ck him. Then he puts on a Prince CD to try and get me in the mood. He actually said ‘Here, just listen to this, Prince is s*xy! All girls like Prince!’

“I think I may have RUN when I finally got out of his car.”

Drive It Home…or to the ER

“Took her to the driving range to teach her how to drive a golf ball. While showing her how to swing hit her in the head on the backswing (not full force). Cut her head open, bleeding all over the place. Took her to the ER to get stitches. Went out to a bar afterwards. She is now my wife of 15+ years. It was a bad date but memorable.”

Awkward is an Understatement

“When I picked her up and went in to greet her mom, they had a 45-minute fight in front of me, and I was too mortified to leave. Culminated with them arguing about why anyone, ‘including that boy on the couch,’ would want to take the girl out to dinner…and then, them literally asking me and expecting answers.”

Escape Route Planned

“Made plans with this guy I knew from a charity I was on the board with. He takes me to a chain Mexican restaurant. […] We go inside, and I try to order some food and he tells me that we are not getting food and that I can’t eat. Then, he starts going off on major political rants which I’m completely opposed to. I ask him if this is all a joke or if he really is being serious. I finally convince him to at least get an appetizer. I was not allowed to choose. He got guacamole (table side), but only had them put onions in the avocado. I was planning my escape when he asked, ‘are you figuring out how you are going to leave?’ Yep. Thanks for the one domestic beer. Bye.”

An Absolute Mess

“I went on a blind date where the restaurant caught on fire, and I slammed her foot in the car door breaking two bones. When your blind date ends at the ER, you are going home alone.”

Her Loss

“A woman I met online (OKCupid), and after a few days of texting, we had agreed to meet for coffee — she arranged everything. […] That night we meet at the local coffee shop and she says: ‘I wish you would have told me you are disabled, I wouldn’t have gone on this date if I had known. You shouldn’t have been born; the world needs less problems.’

“Yes, I am disabled, but it’s only that some of my fingers don’t work properly, and it hurts to walk (but IDGAF and walk anyways). It’s not like I just pulled up in a wheelchair or something. I can do everything a ‘normal’ person can do and some things even better, and yet that’s totally overlooked because my hands don’t work properly.”

Black Magic Woman

“We end up talking about the craziest thing we’ve ever done for a partner. […] She apparently did voodoo magic to make her ex break his right hand. So basically, her last ex was a heavy metal guitarist and had super long hair. He went on tour, and she (without proof) thought he was cheating on him. So, she collected his hair, made a wick from it ([she was a] candlestick maker), and made some sort of like makeshift Haitian voodoo ritual. A day later he broke his hand.”

Rebound to the Max

“During the date, she proceeded to tell me she wanted me to hook her up with my friend in one of the photos (Ouch!). Then, later on in the date, after recovering from that, she started crying heavily – I asked her why, and she replied that we were eating at her ex-boyfriend’s favorite yogurt spot (they had just broken up a week prior and had dated for 4 years). I was so uncomfortable, but I was trying to be nice and funny to get her to stop crying. At that point, I ended the date and told her she needed to let herself process her feelings before moving on to other guys, as that only leads to more hurt.”

Trail of Awkward

“Picnic literally on the Trail of Tears. Seriously. We were both in high school, and I didn’t have the heart to tell him I had no interest in him. His grandmother picked me up and drove us. He put the quilt down right next to the trail marker and proceeded to try to kiss me/tell me about ‘our future’ for the next hour while tourists passed and very quietly read the historical markers.”

Published by everbly


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