>>18 here.

>>20
Totally true...

>>23
Actually... I think "Hey, I was just wondering if you'd like to go out sometime, for bite to eat after work or something" would work wonders... It certainly doesn't sound "easy", and I'm sure he'd be more suprised and flattered by you being so frank than anything else...

Considering how hard it indeed is for guys to flirt with women anymore, a woman almost practically has to make the first move, and make it a direct one, if the guy is to have any idea if it's even safe to proceed any further...