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It takes time. I wasn't always good at it. Shoot, sometimes I use to be downright cringeworthy when flirting. It takes practice. Instead of trying to hard I just started making small conversations with women. Whether in the elevator or aisle at a store. Just small talk and just taking mental notes in regards to her body language. Just keep building your confidence little by little and eventually you'll get better at it. The key is to be completely comfortable with rejection because it will happen often at first.
"Hey how is your day?"smile
"That's a pretty color you are wearing goes good with your eyes."
After compliment go right into next sentence.
"So what's with this weather really windy and cold all of a sudden.Do you know what the weather is tomorrow? I really hope it's nice this weekend because I'm going to a college football game."
Get the back and forth going and make people feel comfortable and listen to their feedback.
Look at where they stand and how far. Some blush,some studder,some hold eye contact or look away,laugh way too much,
Don't put on a clown hat or juggle bowling pins or anything, just say something funny and appropriate to the situation (IOW, don't literally stand there and tell a random joke..."Did you hear the one about the priest, the rabbi and the coke addict...?").
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