I live with a HB 7.5-8 who I dated (not monogamously) for a while and now that we aren't together try to use her as a pivot in groups, and as a wing. I also test out my game on her all the time now that we aren't together, occasionally she caves in and I get her to put out too... Anyhow I tested out this neg on her the other day that got her really mad at me, but I thought it was a good one.

Her - "I think my face looks too droopy, I dunno I think that everything just kinda droops a little but"
Me- "I think your face looks beautiful, its your boobs that are starting to get a bit droopy"
Her - "I can't believe you, that is so mean" <- she was alot more upset than this

Obviously it didn't work, but I loved saying it and it took some consolation to get things moving again. I love having her around as my little guinea pig.

I think that is just mean its not c/f or push pull, it was just rude and mean...

To harsh to be a neg unless perfect 10. Still funny as hell.

Nothing is too far...
It was a perfectly fine thing to say but im guessing you might have just said it wrong.
Say it in a way where shes not sure whether you are joking or not.
Just yesterday I was telling a girl that she stank of fish, but that it wasn't too bad because you could only smell it when sat next to her.
Just say it with a smirk.
Leave her guessing...

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A ship in the harbor is safe, but thats not what ships are made for.

She might have actually found it funny but they ae hoping that if they moan then you will try and kiss their ass to get them back

I highly doubt it seeing that pretty much all girls are sensitive about their bodies.

Oh c'mon! You don't believe what you're saying yourself either!

This one was clearly 'too far' estimating how you said and timed this insult of yours.

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There is NO secret ingredient. Theres just you.

I dunno about that, alot of the things I say could be considered down right insulting, but I have a sort of way I put it, that they know I'm kidding. Also it helps if your just generally witty in conversations.

The original neg WAS definitely too harsh and a bit obnoxious if you ask me. It may not be too bad if you know the chic real well already (even then, as evidenced by the girl's reaction) but there's NO WAY you can use that in a situation where you've JUST met someone, there's just no way. However, with a little tweaking I think it could work:

Her - "I think my face looks too droopy, I dunno I think that everything just kinda droops a little but"
Me- "No, honey, don't be silly, your face is fine. Your BUTT (emphasis) on the other hand..." *exaggerated facial expression like you're hesitant to say something*