I know a lot of this is going to sound like advice from Helen Gurley Brown, but I'm a 45 year old gay man who loves to flirt and charm people, and this is what I know. The main gist is flirting is a game, and anyone can learn it.
For starters, it helps big time if you're attractive. Flirting works best when you're cute, well-dressed and impeccably groomed. You do NOT need to be naturally gorgeous or flawless, but look your best. Extra points for effort go a long way in the looks round.
At the same time, know your audience and who is realistically attainable. Nothing is more sad and pathetic than watching a 4 try to flirt with a hapless 10. But at the same time I don't want to discourage anyone from aiming high. More power to you if you consistently and/or successfully flirt above your attractiveness level. It can happen, but you've got to have GAME, my friend. Good luck.
The first strategy of flirting is to CHARM HIM. Be charming. Just don't force it and don't cross the line into smarminess. Be charming but also be chill.
Smile. A lot. Practice smiling while talking in front of a mirror. If you can do both at the same time without looking like a complete creep, you're golden. A lot of flirting looks like a toothpaste commercial anyway.
Laugh. Laugh at every stupid joke he makes. Don't throw your head back and cackle like a mad hyena, but giggle and snicker and just laugh. Make him think he's funny.
If you can, joke back. Are you witty? Even a little? Can you sound witty? Besides your own good looks, your sense of humor is the biggest tool in your kit. Use it. However, if you recognize that you're weak in this area, let him be the comedian. There is nothing worse than a joke that falls flat.
Flatter him. This is pretty much the over-riding theme of flirting. One of the main goals is fostering confidence in your object of desire. You're not going to get anywhere if he doesn't know that you like him, and you need to make it especially clear that you like him "in that way".
Be expressive. Besides smiling, you can convey desire, admiration, humor, coyness and a dozen other sexy-like expressions with eyes, eyebrows, head tilts and pouty lips. Yes, its silly and a bit actress-y, but try out some sexy, funny, silly and ridiculous poses and expressions. "Mary" me all you want, but at a certain point facial expressions become more powerful than "smooth lines" or more slathered-on flattery.
Touch him as much as you both feel comfortable with. Don't grab his dick (yet), but feel him out (ha) at first and gage his reaction. Touch his arm while you're laughing and see how he reacts. If it's not awkward, proceed: touch his elbow, shoulder, back, etc while you're talking and laughing and smiling and chatting. Put your arm on his shoulder as you're walking somewhere. Gently squeeze, very faintly at first. Put your hand on his hip to guide him to a table or down a hallway. Always gage reactions. If he's cool, slowly bump it up a notch each time.
Avoid sarcasm, don't talk smack about other people, don't express strong opinions about culture or art, and keep everything light and positive. Don't talk about yourself unless asked, don't talk about work (his or yours) or family or anything that might kill the mood. Is the goal marriage, getting laid or just having a little harmless, fully-clothed fun? You decide, but conflict and discord at this stage will just derail everything. You can be real later, or never. It's your choice.
Don't be arrogant, haughty, easily offended or presumptuous. And DON'T be a dick tease. Flirting is all fun and games and often goes no where, even after repeated and prolonged exchanges, and both participants are often fine with that (and may even prefer it). But if you become overtly sexual and then quickly pull back when an arbitrary line is crossed, you've lost the game. By the same token, don't be forceful and never presume the "deal is sealed" or that you're owed anything sexual. Don't go all rapey when your witty repartee doesn't translate to getting your dick wet. Be a gentleman.
