Epic fail flirting stories

Recommended Videos

teisjm

New member
Mar 3, 2009
3,561
0
0
Kazturkey said:
GamerPhate said:
george144 said:
Hitting on my friends 15 year old sister once, in my defence I was a tad drunk and she was wearing a lot of makeup.
She has to be 18 by now though right? Or just move to Canada with her :) lolz
Here in Ireland 17 is legal! Giggety Giggety...
15 is legal here in Denmark, though I would prolly find it wrong to sleep with a 15 year old anyways
 

Sigel

New member
Jul 6, 2009
1,433
0
0
Daveman said:
Oh god yes...

Me personally, I was talking to a girl about biology which according to my friends means I was chatting her up. I then said that when you barbecue a fish you can reach in and scoop out the eyeball and it comes out with this weird jelly stuff (vitreous humour I believe is the term).

Anyway, so my friends took the piss for me trying to chat up a girl with that little line.

Not as good as when me and my friend were chatting up this girl on holiday and I left him alone for 2 figgin' minutes while I go for a piss and when I come back the girl is gone. He'd started chatting about the book the spy who came in from the cold and got chatting with a guy who was nearby while the girl just walked off. That boy is so bloody retarded. Anyway, at least I don't get any more "fish eyes" comments from him...
King_Paco said:
singing to a chick while under the influence is a horrible way to go.
yeah, me and my friend also sung god save the queen to this same girl, but she liked that. thank fuck american women love us brits.
LOL- We are suckers for the accent. You can pretty much say anything as long as it is with a British accent.
 

Hellsbells

New member
Jun 18, 2009
87
0
0
My friend once tried to hit on a chick at a concert and things were going pretty well until he offered to buy her a shirt and accidently pulled out a condom instead of his money. So fucking funny though
 

Straitjacketeering

New member
Jan 3, 2009
608
0
0
george144 said:
Hitting on my friends 15 year old sister once, in my defence I was a tad drunk and she was wearing a lot of makeup.
I've made that mistake so many times.

I remember once I was at a large as party at Smugglars notch Ski resort. (I mean crazy expensive shit) I'm dancing in the crowd and this explosive redhead comes up to me and asks to dance, we start and she asks my name,"Cody! Your's?" "Christina!" "Nice to meet you CHRIS."


Fucked that up all shades of Awkward...
 

Dramatic Flare

Frightening Frolicker
Jun 18, 2008
1,122
0
0
I haven't really failed, but I find it intensely amusing how many NOT drunk girls will try to flirt with me when I'm cashier on graveyard for Taco Bell. I give them something funny but don't really consider it.

best one so far, although this one wasn't initiated by the girl:

-I move quickly with a soda in each hand-
"woah, be careful with that."

-she proceeds to nearly drop both of them, the second one only being saved by me being quick. I stare at her for a second, then grin-
"ma'am, I'm the professional here. methinks you need to be more careful than I do."


HOWEVER, it's not always the cute young ones who flirt. I have had the ugliest looking fifty year old, drunk, smoking women try to flirt with me and then insinuate that I'm not actually annoyed, I really like it. That one made me almost kick them out of the drive thru.

And a drunk gay guy hit on me once. I couldn't get rid of him, so my coworker who's an impressive 280 pounds and looks like a troll comes up right behind me and and says in his deepest voice, "He's mine."

Watching the gay guy attempt to mentally picture that while I just grin was worth every second.
 

iggyus

New member
Apr 18, 2009
1,195
0
0
I once went out with a girl called Jackie. It was my first date so I wanted it to be perfect. I bought dinner and lit candles and what not. So it started pretty awkward but soon we broke the ice and were laughing and joking about all kinds of stuff. However i still wasnt satisfied so in an effort to impress her I started playing with the fire on the candle, Jackie freaked ou
 

Hellsbells

New member
Jun 18, 2009
87
0
0
iggyus said:
I once went out with a girl called Jackie. It was my first date so I wanted it to be perfect. I bought dinner and lit candles and what not. So it started pretty awkward but soon we broke the ice and were laughing and joking about all kinds of stuff. However i still wasnt satisfied so in an effort to impress her I started playing with the fire on the candle, Jackie freaked ou
She was called Jackie, not named Jackie?
 

DerekTheMagicDragun

New member
Jul 15, 2009
100
0
0
My friend was chatting up this girl, so as a joke a brought my friend into the other room and told her my plan, I then walked over to my friend and asked him for a condom, he gave me one which impressed the girl (she was already into him and i guess him being prepared almost sealed the deal, I then went in, waited a minute, walked out and said 'Dude, do you have anything in a men's size?' needless to say he got nothing that night (but she followed me around a bit lol)
 

Kaboose the Moose

New member
Feb 15, 2009
3,842
0
0
Xorghul said:
Fat Man Spoon said:
Walking over to a girl and getting hit in the face with a football halfway there.
Ah. That must have looked hilarious...
And the football kicker definitely did it on purpose.
Or it was the boyfriend that kicked the football
 

Dys

New member
Sep 10, 2008
2,343
0
0
TaborMallory said:
Being nice.
Seriously.

I was turned down 9 times last year for being nice. Not creepy nice, or overly nice, or whipped. Just average nice. Goodbye, self-esteem.
My biggest 'fail' of a pick up attempt was, well, being an asshole to a girl I wasn't interested in (nothing wrong with her, I just wasn't in the mood having fucked up a relationship beyond all saving a few days before). I pretty much shot her down in front of all her friends, in no unclear terms. Later on that night, when I was very, very (visably) intoxicated she kissed me out of nowhere, and I ended up spending a fair portion of the night with her.

...I honestly thought that girls grew out of the "I like assholes" thing when they got out of highschool, apparently not.
 

Altorin

Jack of No Trades
May 16, 2008
6,976
0
0
Dys said:
TaborMallory said:
Being nice.
Seriously.

I was turned down 9 times last year for being nice. Not creepy nice, or overly nice, or whipped. Just average nice. Goodbye, self-esteem.
My biggest 'fail' of a pick up attempt was, well, being an asshole to a girl I wasn't interested in (nothing wrong with her, I just wasn't in the mood having fucked up a relationship beyond all saving a few days before). I pretty much shot her down in front of all her friends, in no unclear terms. Later on that night, when I was very, very (visably) intoxicated she kissed me out of nowhere, and I ended up spending a fair portion of the night with her.

...I honestly thought that girls grew out of the "I like assholes" thing when they got out of highschool, apparently not.
women like a challenge, and saying "there will be no sex" is the easiest way to create sexual tension - even if noone was thinking of it, saying "there will be no sex" is the easiest way to start an orgy.
 

dwightsteel

New member
Feb 7, 2007
962
0
0
I've, on a few occasions, alluded to a point in my life where I just got fed up with not being able to understand what girls were about (mind you this was midway through high school, so I should have figured that rationale was kind of a lost cause on either sex).

You know it's funny, but I've never actually told this story to anyone before. Not because I'm ashamed of it (clearly, seeing as I'm telling it to a bunch of random people), I just never really felt a need. So yeah, you should feel privileged.

I was sixteen. I wasn't shy so to speak, but I was really ignorant. I was the type that broke things down into facts, and thus formed syllogisms based on said facts.

Fact: My friends, most especially my best friend, were getting girls.
Fact: I was (and still am) a big guy, and other big guys I knew were also getting girls.
Fact: I was much more intelligent than most of my friends (I can mark this down as fact, because most of them at some point attempted to pay me to do their homework).
Fact: I was not getting ANY girls, nor had I ever kissed, or even held hands with a female that wasn't a family member.

Based on all these facts, I felt it was reasonable to assume that there was some X-factor that I wasn't aware of, that allowed guys to attract girls.

I relayed all of this to my best friend, who was, and pretty much still is, kind of my living antithesis. He was very much a jock, and I was very much an academic (mind you I was very social. I have always been good with people, which is why I could make friends with a Zach Morris clone). He was fit, and cut, with abs of which I was incredibly envious. I was not fit...at all. He was what you'd expect out of an Ambercrombie and Fitch model, I couldn't make the cut for a JCPenney Big and Tall section. And he was, again, getting girls by the truckload. I told him of my woes and he offered to help me out.

He started calling up girls when we'd hang out, and he told me to observe what he did as best I could, and try to replicate. So I watched him. Suffice to say, he's never been much a witty chap, but it seemed to be his lack of subtlety that was working for him. He'd drop the most thinly veiled sexual innuendos, and these girls would eat it up. I just didn't get it. But again, who was I to argue with results?

I went to school the very next day, and found a girl that I knew of, but we'd never really talked, and I dropped this bomb: "I know we've never really talked before, but how about you come over to my place tonight, and we can shake things up?" I can remember very few conversations in my life word for word. I can remember very few sentences that I've used with such clarity, but this one. I don't know that it will ever leave me. It's the very definition of a turning point.

You know how when you get those awkward silences, those seconds feel like hours? Well I felt like I was standing there for a few days, when the silence was interrupted by roaring laughter. I thought she was having a seizure. She had to sit down to keep balance. This was in our school foyer, full of people. Almost nobody heard me talk to her, but by the time she was done laughing, I'm pretty sure there wasn't a person in my school who couldn't guess.

My best friend, who was well incredibly popular, lived up to his role, and did a fair amount of damage control for my reputation. It was at that point though, that I had one of those "Batman-esque" epiphanies. I vowed that THAT was never going to happen again. I was going to learn the in's and out's of the male and female romantic psyches and I wasn't going to get caught off guard again.

I spent the better part of a decade figuring the whole "love" thing out. It turned me into an asshole for a while, but I'm finally to the point where I've found a nice balance. And it all happened thanks to one sentence, and a lot of humiliation.