Worst date stories

This worst date ever was entirely MY FAULT.

A friend set me up with a friend of his sister. The first night was really casual with a group of us bar-hopping and whatnot. I really liked her. She was very pretty, smart as a whip and funny as hell. The first night she had to leave early because she had an early appointment the next morning, but she called me when she got home and we made plans for the next weekend.

Now I'm very comfortable in a group setting, not so much when it's one-on-one. She lived an hour away so she made all the plans for the date, which I found refreshing. We went to a wing joint to watch the Packers-Seahawks playoff game. I was nervous and was pounding Big Daddy/Tall Boys beers hoping it would relax me. After about 4 of those, I was buzzing pretty hard. We go to a swanky bar after the game and immediately she's like a rockstar in the place. Like this was her Cheers. She's chatting up the bartender like he's her best friend and he comps us some drinks. Enough with the beer, we've moved on to real alcohol, vodka or tequila, I don't remember which. At this point I'm officially hammered.

During one of my many pee breaks, I get a text from a fuck buddy. I spend WAY too much time in the bathroom texting her back and forth. I get back to the bar and she asks if I'm OK. I know she thinks I was in there puking. Well, I keep getting text messages and I keep slinking off to the bathroom to respond to them. All the while ... the mixed drinks are still flowing.

Cut to ... several hours later, I'm guessing. I'm fully clothed and beside her in her bed. Basically, I have no recollection of leaving the bar, getting to her house, NOTHING. I get up and go downstairs for some OJ then weave myself back upstairs. I wind up in her daughter's bathroom (the daughter was at her father's). I basically sit on the toilet for 20 minutes talking to myself trying to piece the night together, how did I end up here, what happened, etc. I finally make it back to bed and just lay there stiff as a board and she says, "I hope you're not just gonna lay there awake all night." SHE WAS AWAKE! Hell, she probably heard me talking to myself in her daughter's bathroom. I was so ashamed.

She wakes me the next morning around 10 a.m., saying her daughter's got a basketball game so she needs to leave soon. I apologize, telling her I don't even remember coming back to her place. "Yeah, you were pretty fucked up. I couldn't let you drive home last night so I let you stay here."

On the hour drive home, I keep getting flashbacks of me practically begging her to let me go down on her. I'm hoping this is just a warped dream I had, but I have to know for sure. I call her, apologizing again and ask if I did or said anything I should be ashamed of. She says, "No. Not really." So I say, "OK, because I'm having these flashbacks like I was hounding you to get in your pants." "Oh, yeah, you asked to eat me out like 20 times, but it's cool. It was kinda cute actually." OMG. I almost swerved off into the ditch. She goes on to tell me that my phone kept going off while we were in bed and twice (TWICE) I picked it up and had a conversation. When I get off the phone, I check my received calls and sure enough, I had two different conversations with two different fuck buddies, one for 5 minutes, one for 20 minutes (!!!).

But as awful as I was, we're still friends. We never went out again because, frankly, I didn't deserve a second date. I saw her a couple of months after this happened at a birthday party and we laughed about it. We even made out a little.

 

... Wow. Those stories from Kokane are utterly nuts and epic. Mine is tame in comparison.

I met a girl through an online dating site, and we chatted a bit - she seemed pretty OK and normal. According to my chatting her up, on AIM and the phone, she was 28, worked as a fashion executive and wanted kids. Cool! We meet up for coffee, and in the course of the date, reveals that she "fibbed" a bit - She is actually 32, works as a cashier at a Gap, hates kids, and HAS NEVER KISSED A BOY. The last part worried me the most, since she was not a hag by any means; she was 4'11", but busty and attractive and a good dresser. I made polite conversation for an hour, but the whole situation was so surreal that I never pushed for a second date.

 

My worst date, if you can call it that, was freshman year in college.

I had just joined the school newspaper, somewhat reluctantly, and met this cool chick that seemed really down to earth and seemed in to me.

We hang out a couple of times, nothing really official, but it's college and we were 19 so any time it was just the two of us, it kind of had the "date" feel, you know?

Anyway, fast forward to about a month after we met. Things are going great, we're hanging out a lot in between classes and after school. She asks me if I want to go to a friend of her's house and I say "Sure, why not?"

I assumed it was some girl she knew, but I was wrong. We get there and it's this guy that's about twice my size and has the personality of a steel toe boot. We're hanging in this dude's bed room (which was awkward beyond belief) and they're just chatting along, to the point where I felt (rightly so) that I was the third wheel.

Then they start joking and laughing and I'm kind of minding my business trying to find a way to leave. Their joking turns to playful wrestling and, as awkward as it was before, it was about 10x worse.

About an hour or so later, I transition the talk to how I've got to go, yada yada yada. I end up leaving.

The next day she thanks me for hanging out and says how great her friend is. I find out two days later they started dating and, now, I'm absolutely convinced I was only asked to hang out so that she could make him jealous.

Needless to say, I stopped talking to her immediately after that.

 

I mentioned a couple of bad ones on a thread a couple of years back. but I was just reminded of another one by a friend this weekend.

After I graduated from law school, I moved to Miami on a whim. I didn't want to work in NYC and a friend told me that the firm he was joining was looking to upgrade the type of practice which I wanted to do. With 36 hours of calling them, they had flown me down and offered me a job, which I took. Having never really driven a car, not really caring cars and having limited funds, I ended up buying a used Mitsubishi Mirage. My Miami friends ripped me constantly about the car, but it did what I needed it to do.

A couple of years later I am newly unattached and on the dating scene for the first time since college. The car was usually a source of self deprecation on dates, but I figured that any woman who cared about my car wasn't worth dating. So one Friday night I am out at a bar and end up speaking with an absolutely gorgeous girl who is with a group which includes a friend of mine. We seem to really hit it off and when she leaves with her friends I get her number. While I am trying to figure out how soon is too soon to call her, unsolicited she tells me that she's free the next night and we make plans.

The next day I call to confirm and we have a great talk. Go to her place to pick her up and she looks stunning. We go outside and she says "is this some sort of joke?" I ask what she means and she points to the car and says that I said that I was a lawyer. I said that I was. She says (and I paraphrase), "you can't be doing that well if you're driving that piece of shit." I try to laugh it off (did I mention that she was really good looking?) and explain that I'm not really a car person, but she won't let it go. She sits in the passenger seat like it's covered in vomit and keeps on talking about the car. I go from being smitten to pissed off before we hit the causeway for South Beach and ask if she wants to go home. She says "I think that makes sense" and I resist the urge not to kick her out of the car in Liberty City and make her walk.

 

Mrs. blacktitleist and I had dated all through high school and survived almost four years of our relationship while atteding different colleges about an hour apart.

My senior year, we decided that we would take a "break" because we had both developed some feelings for other peeps are our respective schools and wanted to explore those situations.

So she sorta started seeing this guy, and I had this major crush on this girl who also played soccer at my school.

Girl was into me too, and we hung out often after class and sat next to one another in yet another class. She thought it was really cool that I always wrote a few notes at the top of my notebook about what had happened the night before in the sports world, so she started doing the same.

Anyways, we had a couple of dates and one of those really, really long telephone conversations one night--kind of like the one Orlando Bloom has with Kirsten Dunst in that horrid movie "Elizabethtown"--when we both realize that the sun has come up without us even realizing it.

Fast forward about a month later, and it's valentine's day and my new lady friend and I are hanging out at my crib before heading out to a late movie. Phone rings, and the new lady friend playfully answers. ON the other end--yup, the future Mrs. blacktitleist.

This did not go over very well with the new lady friend.

We were never really the same after that, and she ended up going to Germany that summer and meeting someone else.

I graduated and moved back home for a job, and mrs. blacktitleist and I ended up getting back together for good about a year later.

 

Blind date. I peer down from my apartment window after she calls to tell me she's parked out front. She's short, and a big girl. Wearing a Dallas Cowboys Starter jacket.

We go to dinner at TGIF's, and we have absolutely nothing to talk about. We go to a bar to shoot pool. I don't know how to shoot pool. It's a character flaw. She insists on playing and she's like Minnesota Fats, meanwhile I'm occasionally completely missing the ball as the stick falls out of my hands. At one point I launch a ball over the table. She giggles. I drink.

I'm trying to figure out how to end this date. What can I do to get rid of her (should have done the pick). So I suggest we visit the adult bookstore located a block from my place, a seedy place that looks disgusting from the outside and the inside. You can almost picture the ejaculation caking the floors. Instead of being repulsed, she says, "Awesome!" Ugh. So in we go, to look at dildos and plugs and gags and porno titles. Just wandering around as she giggles and says how great this is. I'm thinking of suffocating myself with the use of a ballgag and some rubber.

The weather takes a turn for the worse. It's snowing, blowing. I suggest she might want to hit the road to make it back safe - she lived 30 minutes from the town. She says no, it should be fine. We're now back in my apartment. She calls her grandma, who she lives with and says, "I'm just going to stay the night grandma."

WHAT? YOU'RE WHAT? Agggh. I put in National Lampoon's Vacation, one of my top 5 favorite movies. She sits there stone-faced, doesn't even ever crack a smile while I'm dying laughing.

"This isn't a funny movie," she finally announces. Christ.

Fuck me. I'm now tired and tell her she can take the bed and I'll sleep on the couch. The couch was stained with...I don't know what. It was furnished when I moved in and I still hadn't removed it or the stains. I was quite the romantic back then.

I go to sleep on the couch and wake up energized, because I'll be rid of this girl. She leaves, we give an awkward hug. Five minutes later, a knock on my door.

"My car doesn't start."

AAAAAAAHHH. We call a tow truck and I have to go with her to see how it's going to turn out.

"If they can't fix it, I might have to stay another night."

Thankfully they fixed it and she drove off into the late-morning snow.

 

Asked a girl out.
Went to restaurant.
10 minutes in, she says she's not interested.
I leave.
The end.

 

Worst. Date. Ever.

Sophomore year, high school. I don't remember the ostensible dating activity that took place that night. Probably a movie and dinner. It was raining most of the night but for some reason I thought my date and I could ... ummm ... discuss Buddhist philosophy while parked at the ballfield where I played peewee ball. It was undeveloped (i.e. unpaved).

After our um, discussion, the car was rendered immobile by the interaction of lots of rain and bare soil. Had to call my folks to come get us. Girlfriend was understandably mortified and pissed. Our dating relationship ceased soon thereafter but we remain friends to this day.

 

This one is good. And better when done in "Kevin voice."

 

No total train wrecks here. Just uncomfortable situations.
One girl, I met through match.com. We went through the usual routine of exchanging e-mails and talking on the phone, and we finally go out on a Saturday afternoon. I usually like to do something fun on a first date, so I suggest a mini-golf place nearby.
"No."
OK, how about bowling?
"No."
Lunch and a movie?
"Nah."
Just a movie?
"I don't think so."
So finally, I ask what she wants to do. We end up driving to her trailer trash friend's house 30 minutes away for the friend's kid's birthday party. The kid is about 5. So we're in a nasty trailer, with screaming kids, country folk sizing me up like they're about to kick my ass just because, and absolutely no chemistry with this girl. Plus, she's talking to her friend most of the time.
We finally leave after about an hour. It's late afternoon now, and I'm getting hungry, so I ask if she wants to grab something to eat. At least give it one more shot, I figure, and then bow out gracefully after dinner.
"No. I'm not really hungry."
We end up back at her place (she drove all day and I left my car there) and spending another 30 minutes sitting on her front porch as she smoked a couple cigarettes and talked on the phone with another friend.
Just a miserable day.

 

Another girl I knew was more like a series of bad dates.
We went out a few times and seemed to be clicking OK. Made out a few times but never really got close to consummating the relationship. The closest we came was when she called me saying her blood sugar was low (she was a diabetic) and we went to McDonald's and then her place. But looking back, I don't think she was frisky, just diabetically drunk.
Still, I was OK with that. She was a nice girl and I figured things were just moving slow. I was at a point in life where I was willing to show some patience.
But for every step forward, it seemed like we took two steps back. I came up with some damned creative date ideas (ice skating, a visit to a "cactus plantation" -- really just a greenhouse that specialized in cacti -- a flea market/crafts fair type thing, movie night) and she never turned me down. She just didn't seem to want to move forward.
So this goes on for about six weeks, and I start to feel like a stalker. I'd call her every day since it felt like we were in some sort of quasi-relationship and she never told me to buzz off. We'd go out once or twice a week. Finally, she says she's looking at going back to school in Texas in a few months and isn't really looking for a relationship now.
It was kind of a relief, to be honest. Nothing worse than standing around with your dick in your hand (metaphorically speaking, sort of, since that was the only action I was getting out of that girl).