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Let me ask you this. How do you walk the line of playful smack talking and offensive put downs? I understand that I want her to be on the defensive, but what happens when she just thinks I’m a dick, instead of flirting? I’m just saying that it seems that she could get the wrong impression, and that will ruin my chances. I can’t care about that though.
All that matters is if what you’re doing builds attraction or not.
If you’re teasing her and she’s getting further away from you and paying less attention or getting genuinely upset, then you’ve crossed the line.
But if you are teasing and she has this “how dare you” smirk on your face or she playfully hits you or teases back, then you haven’t. It depends on the girl, and you will know because the more confident she is, the more teasing she can take. Unfortunately it will take some experimentation and failure to find the right mix but the key is always to listen to the feedback she’s giving you instead of getting into your own personal world of delivering lines you got form Casanova007 on some seduction forum.