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How to initiate flirting?

I need to learn to talk to this one "special guy" he is like my type... my friends think he's decent and say that it would be perfect if we get together. But the problem is that we don't talk to one another. He's friends with all of my friends but he is not that close to me. He even knows my sister! Today I talked to him kinda... but not an actual convo. and then we always start talking on Facebook. but I start the convo because my friends tell me too... its terrible I know. I need to talk to him in person but I'm always shy. way to shy to talk to him. I smile at him... it depends on his reaction. sometimes he just raises his eyebrows, and other he smiles back, or he say HI *insert my name* and I just smile like a dumb ass... I'm hopeless at least that's what I think. I'm not sure I am really hoping you guys can help me. this guy seems awesome but he is really hard to talk to for some reason... I have never had such difficulty talking to one guy before... anything really helps but mostly flirting tips... convo starters... and maybe some body language techniques, thanks for reading :)
How to initiate flirting?
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