Taken from one of the masters (not me, Rollo Tomassi):
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Iron Rule of Tomassi #9
NEVER SELF-DEPRECIATE under any circumstance. This is a Kiss of Death that you self-initiate and is the antithesis of the PRIZE mentality. Once you've accepted yourself as a "complete douche" there's no going back to confidence with a woman. Never appeal to a woman's sympathies, her sympathies are given by her own volition, NEVER when they are begged for. Even if you don't seriously consider yourself pathetic, it never serves your best interest to paint yourself as pathetic. Self-Depreciation is a misguided tool for the AFC, and not something a true DJ will ever consider.
That said self-depreciation is pervasive and something that I myself have been guilty of in the past. You have to be hyper-aware of it and unlearn it. You have to catch yourself in mid-sentence so to speak. Women operate in the sub-communications and when you OVERTLY admit to a lack of confidence you may as well just LJBF yourself. That's a strong impression you wont recover from. Women want a compitent, confident, decisive Man not one who's self-image is that of a "complete douche" or even a partial douche. I should add that when you become hyper-aware of this you can also turn it to your own advantage when AMOGing or you're working a girl with a self-depreciative BF or other suitor. It's all too easy to reinforce her estimation of a guy like this by covertly confirming it for her, while at the same time playing up your own confidence and value.
All of this is not to say that it's wrong to recognize your own weaknesses and understanding when you're in the wrong. It's simply how you go about addressing them that's the point. We had a thread here not too long ago about admitting when both of you are wrong and this got me to thinking about healthy ways of communicating this. There are plenty of way to assume the responsibilties of fault that aren't self-depreciating. The easiest way is to always adopt the attitude that you're 'getting better all the time'. This mentality fosters confidence and projects ambition, whereas self-depreciation shoves your nose in the dog sh!t and says "please love me anyway?"
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Never put yourself down in front of a girl.
Although your line was not that bad, but she managed to turn it around on you, perhaps because she (and others?) knew it wasn't true.
Maybe just to shake things up after she said "well, that's one", you should have said something like "good thing I'm gay" or something like that, just so she couldn't have the last word.
