Awful Date Stories!

Pick

I once met a guy from off OKC. He showed up late, was obviously sclubbier than his picture, and his hair had a greasy sheen. Anyway, we end up talking for about three hours, but after about 20 minutes it's just because I am fascinated by just how badly a date can go. He tells me about his many failures, how everything disappoints him, how he doesn't like his job and wants to quit and just read comics all day. He then moves on to all the things he is good at, and tells me his highschool teacher told him he was "good at commas". He doesn't drop any indications that he's actually accomplished in any way, there were no awards or anything of that sort. The conversation then moves to him telling me about all of his exes and wanting reassurance that I am not like them, with specifics. He awkwardly tries to figure out if I have any money. At the end, he tells me his idea for a novel, which is the exact premise of Early Edition but with google, and instead of CBS heartthrob Kyle Chandler using his knowledge of tomorrow's paper to save bingo ladies from anacondas, it is about an asshole with eerie similarities to my date using this power to enrich himself and get a supermodel girlfriend... but is he fulfilled?! He hasn't come up with the second half of the book, and when asked what the theme is he says "superiority". I tell him I had a "nice time" and that I have to go. He says, "that's it?" and stands there fuming like the Arthur clenched fist meme as I go. I get into my car and burst into laughter, because in the span of three hours, he never asked my name.

Dr. Quarex

My first real girlfriend involved her mom on our first real date, though to be fair it is because I met her on IRC, our first meeting was in some completely unrelated person's uncle's house for an IRC meetup, and our actual real date required me to drive the six hours to be in her city so we spent a fair amount of time at her mom's place so she could be convinced I was not going to murder her daughter 

Best awkward part of that date was me being presented, for the first time in my life, with a steak, and trying to cut it with a butter knife. The perils of being raised in a nearly-vegetarian household. Her mom was very understanding about the mentally handicapped boy her daughter brought across state lines though.

Kaewan

I've been on a lot of weird dates; from a girl locking me in her house, to spooky witchy graveyard sex. My most awful first date would have to be about 4 years ago. This was back when I worked as a bartender at a fancy cocktail bar. The kind where every drink had 6 ingredients and every syrup or shrub was made in house.

There was this one gorgeous woman that would come sit at my bar whenever I worked, lets call her Mary. Mary would always smile when she saw me, laugh at all my jokes and be disappointed if I was away for any reason. One night Mary suggested we go for drinks. I joked about it being a date and she was delighted.

Back then I had a go-to date spot. It was an upscale restaurant where my good bud was head chef. Naturally we got quite the hookup, my scallops and her seafood risotto were both comped. All I had to pay for were the drinks. Afterwards Mary and I walked through a park holding hands, watched the sunset; it was quite magical. Later on when I drove Mary home she insisted I walked her inside. Mary showed me her liquor collection and I made us a few cocktails. We bonded over every little thing, from music to movies to booze. After some point we started making out and not before long Mary dragged me to her bedroom for some amazing sloppy sex.

Now at around 3 am I bolt straight up with my stomach rumbling dramatically. I don't make it out of bed before my bowels decide to violently purge. I rolled off still half drunk while I cupped my butt attempting to block the flow. It was like trying to stop a fire hose with a tennis racket. My foot still asleep and the room spinning I stumble towards the bathroom in the dark. Inadvertently I smeared shit all over the wall fumbling towards the door. I finally made it and I was in complete shock, my mind racing. I stood there staring at my reflection in the moonlight, ten minutes pass in total disbelief. It had to be a nightmare, I was expecting Mary at any moment to wake up screaming in horror. Nothing happened and I got an idea.

I rinsed off, gathered my belongings and snuck downstairs. I found a pen and paper and left a note. It read, "YOU SHIT YOURSELF, I LEFT."

angerbeet

This was way back when I was a teenager but internet dating was just becoming a thing and I went out to the movies with this guy, who seemed a little out of it but was OK looking and whatever. He tried to give me a handjob during the movie but I stopped that. We went out to a park afterward and swang on the swings, and eventually came back to my place. Sex was pretty much going to happen so we start making out and getting undressed, it turned out he had extensive burn scars all over the bottom half of his body. Turns out he had severe mental problems and had doused his legs in gasoline and lit them on fire because "the top half is the angel and the bottom is the devil."

Which was better than the fry cook who had a Tasmanian Devil tattoo on his chest and came from being fingered up the ass, then proceeded to do the infamous "angry dragon" move when I came in his mouth, he choked, and it came out his nose. He at least just left afterwards.

DeathSandwich

One of the first dates I ever went on in high school was with a gal who after we got back from dinner and a movie and went to make out for a little bit discovered I was ticklish along my ribs. She would not stop tickling me even when it stopped being fun and started hurting. She tickled me so much she actually made me vomit. After I went to the bathroom and cleaned up, she wanted to do it again.

One More Fat Nerd

Had a first date with a girl from OKC. She was about as expected, slightly heavier than pics indicated, nice boobs, cute. Had burgers then went bowling. Ran into an acquaintance (M) out with his wife (B) at the bowling alley. This is when things went weird.

To preface, I consider any first date I survive to be acceptable, so I was never particlarly upset at any point, just increasingly bewildered.

M was fairly drunk when we arrived and noticed each other. He invited us to bowl with him and his wife. We agreed and everything went smoothly for like 30 seconds. Then M started hitting on my date. The starting line was "I like thick girls, all the girls I've dated, except B, were thick." It continues from there. Within five minutes we have a description of his genitals, their pet name and dimensions. This includes how weight gain/loss has changed them over the years.

I'm bowled over. Both because his wife (twig-skinny, literally a ballerina) is five feet away, and because somehow this approach is working. My date is into this. I'm not even mad. Being incredibly straightforward about your sexual interest right in front of your increasingly upset (but trying to hide it, "oh M just has no filter when he's drunk haha" *thousand yard stare* ) wife is something I had never even considered as a viable strategy. Its not like the guy was gorgeous or anything. Average height, average looks, average shape.

As the night goes on, his wife starts to hit on me, but not in a "oh this is polyamory" way, in a "desperately trying to make the husband pay attention to her" sort of way. Culminating in her getting a strike and taking a congratulatory running leap onto me, wrapping her legs around me and planting a big kiss, (eyes glued on M the entire time) . M does not appear to notice or give a single shit.

By the end of bowling, my date, M and myself are somehow discussing kinks, and how her personal kink is that she has a strong preference for anal, to the extent she would prefer to never have standard sex again. B is stewing. The decision is made to go to Kroger, buy beer and head back to their place and hang out. At Kroger, M goes in to buy beer, my date goes in to pee (they exchange numbers inside, I found out later). B and I are left in the parking lot. I talk to her for a bit, she apologizes for M and calls me a "gentleman". This is the only part of the evening that actually stung. She is sobbing increasingly hard over the course of this conversation. I decide I'm done.

When they emerge with beer I make an excuse to go home. Somehow this girl thinks the night wasn't insane and asks online the next day if I'd like to go out again. I didn't answer lol.

Seven years later, M and B are still married and have two kids. According to a mutual friend, he cheats on her multiple times a year, and she is open about accepting it because she doesn't feel she can do better. Happy Ending!

yeah I eat ass

I remembered a more recent one that was more of just a very awful date moment, the rest of it was fine. She had just told me that her mom passed away and I was a little drunk by then and said "oh, I'm sorry...did she die when you were alive or sooner?". It was one of those moments where she looked at me like I was either joking or an idiot but thankfully I recovered and clarified what I actually wanted to ask. It's still one of the stupidest things I've ever asked someone, and that's saying something.

Radical and BADical!

Me on a date in car many years ago:

Me: so where do you want to eat?
Her: Actually, can you pull over a second? I really need to talk to you.
Me: Ok.
Her: I cheated on you last night. With Dave.
Me: ... ... ... Really?
Her: Yeah.
Me: So, I guess I'll take you back to your parents house...
Her: HA! I WAS JOKING I DIDN'T CHEAT but I guess you'll really never know.

Shoulda broke up with her but I stayed with her for another year.

Three Olives

I guess this was about two years ago, I picked up this guy at a bar and took him home. He was cute, I was horny and drunk so when he told me he had been to rehab for meth addiction I didn't think too much of it. I mean I'm gay in a big city and into the bar scene, I know people that have had meth addictions before, they aren't unfuckable. He was cute, clean, good body, all his teeth and they were clean, meh, we all make mistakes.

So I take him home and fuck him and pass out at some point from the alcohol. Well, when I say pass out I mean I blacked out at some point. He's gone, the sex was good, he didn't steal from me, not too bad.

Until I went to the bathroom and picked up a shirt to put in the hamper and found a syringe under it. Empty with just dark stuff that looked like blood in it. Freaked out, put it in a metal container, then in a bigger plastic box, then in a metal cookie tin, then in a bigger box and then in an ever bigger box and threw it in the trash.

Went to work and then I got a itch on my arm, probably a mosquito bite or something. And then I noticed it was right over a vain and it kept itching and unconsciously itching it. And remember the syringe. And blacking out. And I'm not the kind of person that would ever do injectable drugs but oh my god I completely blacked out, I don't remember really anything after fucking him.

So yeah, that was a fun 12 weeks convincing myself that the meth addict that I took home from a bar to fuck might have injected me or I blacked out and injected myself with meth, looking up pictures and video to see if it was even a place you would inject drugs (It apparently was) while I waited for an HIV test.

– David "g0m" Dolan (@g0m)