Worst thing you've ever said to/asked a woman?

I was talkin to a real artsy girl the other day. Not normally my type, but she's real cute. I went on a joke/rant about a professor who models himself after Agent Smith's character in Lord of the Rings. Ridiculous mullet, stupid earrings, 4 rings on each hand... plus every day he wears a black suit, black tie, black shirt and lace up black leather boots. How fucking losertastic/nerdvirgin does this guy have to be?

"I speak Elvish and have 6 tattoos of Lord of the Rings, asshole."
 
I think it went something like:

You're a fucking cunt, a dirty fucking cunt you fucking whore. A fucking slutty cunt whore is what you are you fucking cunt.
 
there was a good friend of mine that i was porking and she decided to call it off so she could get back together with her ex and be in a relationship with him.

long story short the two of us were boozing at a bar a few nights after she'd "cut me off" and she was helping me look for girls to hit on. and i basically said something along the lines of "lauren, you're not the most beautiful girl in here, but i'd rather take you home than her."

she was fucking pissed.
 
not said to really or asked...but a girl once asked me if she was a good fuck toy...and i was looking to get out of said relationship...so i said yes you were. relationship ended.
 
JoMo said:
I think it went something like:

You're a fucking cunt, a dirty fucking cunt you fucking whore. A fucking slutty cunt whore is what you are you fucking cunt.
Click to expand...

mine went something like that as well along with insulting her whore of a mom
 
I got into a pretty heated argument with my girlfriend at the time over some useless bullshit she was always starting.

Fed up, I said, "It's no surprise your dad cheated on your mom... You're all fucking crazy."

She had always had issues with her dad and I went for the jugular with that comment.

:shrug: I guess it's context about how bad that really is, but I have never forgotten how much of an asshole I felt like after it came out.
 
i told some fat chick at a bar that she was kidding herself if she thought i was hitting on her and that she should move along and go graze in that pasture over there and she got her boyfriend to swing at me.
 
I was told to call this extremely large girl "boom-boom". I didn't like this girl at all so asked no questions before proceeding to call said girl boom-boom. She borderline shits her pants and bounces around my kitchen like a retarded gorilla. I later find out that a guy who had fucked her described it as "boom-boom.. boom when you stick it in and boom when the fat recoils back at you".
 
I said, "I like my girls really fit and thin, like anorexic almost" and the chick flips out and goes "my SISTER was anorexic"

lawl, never talked to me again after that. I still maintain she was a really crazy bitch though.. such a harmless comment
 
too many to count

the worst was probably calling some chick at a bar with a facial scar "tony montana" all night
 
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