If you see a cute guy on the street just smile and say hello. It’s that easy. We men are quite simple creatures, as a rule.

I have a friend who is the male version of yourself (same age and also fit, educated, and extremely attractive). But he’s not the most sexually assertive guy so he ends up dating not the women who have the confidence to talk to him.

Personally, I think the strongest move is walking up to a guy and teasing him a bit. Make fun of his shoes, hair, whatever in a fun way that’s not overly mean (“might be time for a haircut don’t you think?” —followed by big smile). Stuff like this starts the convo off on a light note and gives him a chance to be witty back.