Ok Basically i was at a bar and i saw a girl i know bt never knew how to chat her up, so i approached with a friend, made a little small talk and then gave her a neg and from there it went down hill.
This is how it went:

me:(neg) i like your skirt, i see a few girls wearing them lately

her: oh my god, that's the worst thing you can ever say to a girl

her: can't believe you said that

me: sorry, it does look nice though.

Is this reaction because i already know her and she knows what im usually like or did i do something wrong?

Jestic

This is my first post so go easy on me! personally i like the neg, its not harsh and if said correctly could come across as playfully. However, maybe this is where you are going wrong. Depending on the tone of your voice and the manner in which you said the neg the girl could percieve it in different ways.

What was her tone like when she said "oh my god, that's the worst thing you can ever say to a girl"? was she being deadly serious? even if she was you could have still rolled with the punches, i dont know much about shit tests but that sounds like a major one to me. For you to say "sorry" was probably the worst thing to do in this situation, it shows weakness and really you should be opening the set as an alpha.

Try not to dwell on the neg for too long, as soon as youve said it move straight into a routine....."hey did you guys see the fight outside?" otherwise you might come across as an asshole whos just trying to insult them.

Hopefully ive helped, like i say...FIRST POST!

For you to say "sorry" was probably the worst thing to do in this situation, it shows weakness

I agree with Diamond, even if you did mess up the neg, you should have stood your ground. Your response should have been something like, 'really, I thought calling a girl FAT was the worse thing I could say lol', (laughing at the end to make it playful).

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Keep people off-balance and in the dark by never revealing the purpose behind your actions. - Robert Greene

cheers man that does make alot of sense.

I did say in a bit of a serious tone maybe should have been more playful.

She said it in a slightly embaressed tone she was laughing it off slightly.

Thanks for the advise m8.

Welcome to the forum. Yeah, the first thing was that you already knew her. And the neg was a bit uncalled for. It made no sense saying it other than to point out that a lot of girls wear them... A neg should be an offhand comment that goes wrong and best of all, come up naturally in conversation. Or be delivered playfully.
Second: Never apologize for something like that!

Did you smile when you delivered the neg? You shouldn't of apologized and then just stacked with a DHV story instead of letting her comment on it. I would of said that neg but then said something like it reminds me of my ex she has the exact same skirt, I can't even talk to you now. Something along those lines.

you should have wrapped a compliment at the end of the same sentence.
never say sorry,, throw and go, jump into a next conversation topic
smile? body language? or she was having a bad day? the energy and the mood? check those out cuz they`re important factors

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Gotta Fuck em all! Pokemon!

Sorry should be erased from your vocabulary!!!! Thats somthing that took me a long time to learn. Never use the word sorry ever! lol not around women, men, doesint matter it makes a person look weak.

Remeber that point is to not care so you should have said somthing like "You sure thats the worst thing a guy could say?" and just laugh.

Remeber you are an alpha you dont care.

I find to start you should use simple negs that she cant get mad at....things like "your nose wiggles when u smile" or "you have an eye goober"....then once you have felt her out a bit you can start pulling out the big guns.

Oh oh oh! Calm down, mates...

This is a girl that you already know... Why would you wanna neg her? Why would he wanna bring out the big guns? And why would he wanna reward her by doing A3 stuff?

There is only two good reasons to ever use negs.
1. If she would otherwise assume that she has a higher value than you or that you are hitting on her.
2. Teasing her to get a playful mood going.

Try seeing negs instead as false disqualifications. They are there to not creep her out by being to forward.

me:(neg) i like your skirt, i see a few girls wearing them lately.

her: oh my god, that's the worst thing you can ever say to a girl

her: can't believe you said that

me: hahaha, honestly though, out of the girls I saw wearing the shirt, you do look the sexiest in it by far( look into her eyes when you say this, with serious I WANT TO FUCK YOU LOOK)