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I had friends set me up on a blind date years ago. I talked to him on the phone for a month before agreeing to meet him. He said he had put on the typical "holiday 5" but had joined a gym, and told me he drove a Lincoln. I met him at a restaurant where I saw his "holiday 5" had been accumulating for decades, and his Lincoln was 20 years old with a missing fender. I ordered a cocktail and he said, "I don't like to spend money on that stuff. I always drink water." Then he asked the waitress for "any cheap specials" they had. (This was Applebees for Pete's sake!) I told him I'd pay for my own dinner since that seemed to be an issue, whereby he called the waitress over, asked if we could order a bottle of wine, and changed his order from just an appetizer to a steak. He spent the entire meal talking about himself and the fact that he needed to live with his mother to take care of her but he was in the market for a girlfriend who'd be willing to quit her job to stay home to do that for him. When the bill came I reminded the waitress we had separate checks. He was upset, to say the least. I reminded him that I was paying for MY dinner, not his. HE ordered the wine and upgraded to a steak. I had a burger and one glass of wine. The waitress comes back, I pay my bill and get up to leave. He is now grabbing me by the arm and screaming at me. Says "I can't afford this sh*t!" The manager comes over, I explain everything and leave. Later that night my friend calls to tell me he was actually arrested because he couldn't afford to pay the bill, and I should have never embarrassed him like that. We haven't spoken since.

#1

"I've got a friend you'll really like" - The opening words to an evening where a girl I really fancied 'friendzoned' me by introducing me to her best friend. It was a weird three sided date (she insisted on coming along herself to make sure her friend would be OK, but didn't bring a partner of her own). The girl was, without a word of exaggeration, like a female version of Trump.

Opinionated, mouthy, unpleasantly rude to just about everyone (even her friend), racist, sexist, every kind of 'ist' you could list and she also had a faint smell of onions about her that just infected everything within a 500 yard radius (which made the 'dinner date' even more difficult to stomach). It was a pong that just took up residence in your nose and didn't quit. I could still smell it for days afterwards despite repeated showers and even shoving a vicks stick up my nose.

She also drank like a trooper, swiftly racking up shot after shot, getting more and more drunk and loud and obnoxious. They say time passes differently when you're enjoying yourself, and differently when you're enduring abject misery, and my god that evening felt like it went on forever.

At the end of the evening she tried to kiss me and I sort of awkwardly ducked out of the way and ended up accidentally headbutting her in the chin which made her cry, and by cry I mean "emulate the noise a wildebeeste would probably make if you tried to introduce a traffic cone to its hind quarters forcibly"

The date sort of crumbled apart as I ran for my bus, apologising as I ran.

Her friend (the original girl I had a crush on) emailed me the next day to tell me that I was rude and obnoxious but could apologise by arranging a second date. Needless to say that did not happen.

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    #2

    First date. He said, "I really want to sleep with you tonight," and put his arms around me from behind in a tightening grip. last date b/c I floored his sorry a*s. Note to everyone: Don't grab anyone from behind. You may be "strong", but we may have PTSD and react by trying to kill you with our teeth and elbows. So I was *his* worst date, from what I later heard. Good. Creep that he was.

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    #3

    The date that wasn't

    Met a guy on POF. Talked for a couple weeks then met up for 1st date at my favorite restaurant.it was great had dinner then got ice cream. Made plans to go to the movies the next day. I waited and waited I texted I called I was ghosted. I was so sad I thought he really liked me. Then just as I'm heading to bed completely depressed he msgs me. He apologized and said he really liked me and was to embarrassed to admit he couldn't afford the movie. I told him it was ok but he should have just told me and we could have just hung out or something... anyway I gave him another chance and we've been together 10 yrs and married for 4

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    #4

    Oh.. sooo many.. but probably the then 25yr old guy who belittled a waitress who'd forgotten the lemon for his coke, calling it a job for losers and idiots.. he was unemployed and living with his parents. I tipped her extra and never saw the guy again. You disrespect waitstaff, you're out

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    #5

    I dislocated my knee, put out my arms to stop my fall, still hit my face. I wound up with two broken wrists, a fractured cheekbone, a black eye, crutches, and a brace from my hip to my ankle. We dated for nearly three years after that.

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    #6

    It wasn't a "date" per se, but I went to see Endgame with a girl I had a crush on. She asked if it's okay if she brought a few other friends; since it wasn't officially a date and I didn't want to seem creepy, I agreed.
    Turns out a guy she brought with her has a crush on her, too (despite that, we got along pretty well). However, our mutual crush was constantly holding hands and acting flirty with another girl who came with her. At that point, "third-wheeling' didn't even correctly encompass the whole experience, it was more like... some kind of queue.
    In the end, the experience wasn't totally unpleasant. The film was great, they were all cool people and we even had a good laugh. But the (not) date part was hella awkward. As far as I know, she ended up with yet another guy I've never met in my life - but I'm glad she's happy :)

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    #7

    I have two that are comparably horrible.
    1) it was a blind date. He was soooo creepy and weird. Like almost serial killer vibes. We had nothing in common. He tried to make me go with him to a church and play on the organs because he found out I used to play the piano.
    2) went to a tea house. He kept arguing whether tea is stronger than coffee (I didn’t care). He was correcting me every sentence to make himself look smart and then to top it of he told me he had to go to the bathroom. Instead he left so that I had to pay for him too. He waited for me outside and wanted to continue dating…

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    #8

    Everything was ok until he got down on all fours and asked me to wrestle , he said there wasn't too much poo in the grass and when I said no he said I was making things super awkward...

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    #9

    Well, not sure what I'd call it as the guy wanted to take me on a date and I said no. He invited himself out to lunch with me, my sister, and her then boyfriend (I was going to drive them to the Harry Potter movie after lunch) and was a total a$$. I had been ill and he insisted on ordering something I couldn't stomach (the plan was to share, and my sister was so nice to share her and her bf's food with me). Then he was loud and rude in the restaurant, talking about how he hated fat people, and super sperm so big "you can lasso them and ride 'em round the room!" There were other comments about women being submissive and how much he liked that. I was MORTIFIED! Everyone was staring at us, and I can't blame them. So I paid for ALL our lunches to get the heck out of there. He called later to apologize and offer to take me to another bar to "make it up" to me. NOPE.

    He runs in the same circles me and my now husband do. We intentionally rattle his cage because it's so much fun to watch his impending implosion, and it gives any woman (or anyone) who is cornered by him a way out.

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    #10

    In general worst relationship... He hated my friends for no reason and always badmouthed them about things that were his fault... I told him I was ace because I trusted him and he said it wasn't real, I was doing it for attention, I wouldn't be ace if we were together later in life, etc... I stopped eating lunch because I had body image issues, he said "Clearly I don't care if you're fat, I'm with you now aren't I," so I stopped eating breakfast and dinner too... Whenever I brought up his toxic behavior that I was concerned about, he guilt tripped me until I ended up apologizing... After the break up he kept staring at me creepily and following me around... I am still scared to love anyone and have not been in a relationship since... Yeah. Not exactly a good experience.

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    #11

    Just for context, I'm a widow in my seventies. I thought maybe I'd try this dating thing after being alone for some years. I found this fellow who sounded okay on a free dating site. We met at a local coffee shop. I paid for my own coffee. He talked the entire time about himself, then got interested in somebody's recumbent bicycle. He went over to talk to them and left me alone. I left. I don't think he even noticed. I think I'll just stay single, thanks.

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    #12

    Many years ago I invited a girl to our Senior Prom, would have been my first serious date in high school, after a few party/recreational dates with other people.
    We got there, said hi to friends, she then told me her religion forbade her from dancing.
    I was kind of surprised by that, I felt that I should not dance with others if I could not dance with my date, so just sat and watched.
    Kind of a weird night.

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    #13

    Well, it wasn't really the worst, but it's definitely memorable. It was my first ever date, actually. It was the day before Valentine's Day, and it had snowed pretty good the night before, so we double dated with another couple and went sledding in his backyard. After we were done, we got in his car so he could take me home, but the other couple's car got stuck in the snow. It's a good thing we were at my date's house, because he has ten siblings and they all came out to help. His dad got out the big van and tried to pull the car out with it, but then the van got stuck too! It took almost an hour to get both vehicles unstuck.

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    #14

    So not technically a date but bad relationship. I would always make efforts to try and hang out with him, and he always turned them down. Broke up with him and I’m in a great loving relationship with an amazing guy.

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    #15

    I ended one date in hospital after eating a desert that contained nuts but didn't list them as an ingredient. I was halfway through the desert when I started to realise I was having a severe allergic reaction to it. I used my epipens and anti-histamines but still had to call an ambulance and spend the night in hospital. There was no second date but the restaurant did cancel my bill and send me a £50 voucher.

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    #16

    I went out to a big shopping mall with him. He bought me something I wanted (didn't ask for him to do that, he just shoved money out when it was rung up). The second thing I saw he said, "You already got a toy" or something condescending like that. I had my own money... I broke up with him shortly afterward. Shortest boyfriend I ever had, lasted only a few months.

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    #17

    My first date, worst date, and last date with this person.

    She found a Silk moth outside, and she was paying more attention to the moth than me. I eventually went up and ordered the food, and she said she didn't want anything, and then left. I never dated her again, and we broke up a few months later.

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    #18

    I'd say the worst date is December 7, 1941.

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