Importance of Wingmanship
You could use this with your wing anywhere. It'll be best to use it in a place where you know you'll see the girl again, like school, class, work, etc.
You say (be jolly): "Hey, my friend called me gay for saying that you're cute. Is it UNMANLY to say 'cute' or something?"
Your wingman (closely behind you): "Dude, chicks are HOT or BLAZING, not 'cute'! God, I thought I was dealing with a man here. She probably thinks you're a wuss."
You say: Yeah, whatever, go eat some beef jerky or something bro. Anyway, ignore him, he's just a walking glob of testosterone. Anyway, what's your name?
In this scenario, the girl will get the idea that you're a fun guy who isn't afraid to be sensitive. This is exactly what we want. Make sure your wingman's demeanor is like an "intelligent idiot". You be calm, cool, and amused. Basically, you play straight man to him.
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Or you could approach a girl or group of girls with the classic, "Hey, my friend says I appear gay in this shirt. Is this something I should worry about or do you think he's just joshing?"
Have your wingman say shortly after, "Yeah whatever, some guy named Josh is probably checking you out right now."
You both be playful and joyful. After she responds, just dive in the conversation.
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Take these two examples and run with them. Learn from them, apply them in real life, use them as a guideline. Do whatever--as long as you get SOMETHING out of it.
"We're all born pick-up artists, only society prevents our true potential."