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Well I base myself on Mystery , he did say I can compliment a girl but not based on her looks . The whole qualification sceme of hook and release or whatever . why is boosting morale soo frowned upon by the way , girls get soo happy when I compliment them on insecurities .
If something is working for you, why ask the question? But to answer your question, if you compliment an insecurity you are rolling the dice on her response to it and it can end up positive or negative. If you don't acknowledge it, you don't lose any points nor do you gain anything.
Again, if it works for you...don't let my opinions influence how you act around women. In fact, I would encourage you to write a post detailing how you do it in order to help other guys out.