Conversation starters...

Hello all you awesome advice-giving ladies out there...

So here's my issue. The last relationship I was in was over five years long, and started in high school. She was the first of only two girls I've ever asked out in my life. The second barely counts, but that's another story. Anyway the point is, I have almost no experience meeting and flirting with women since in high school dating was not high on my priority list and since the first girl I ever did ask out ended up becoming a long-term girlfriend. Well that relationship ended almost a year ago and for the last few months I've been feeling like it's time to start mingling and meeting again.

So I guess my question is, do you like to be approached by guys who you don't really know and flirted with, or do you like to be the initiator? If you like a guy to initiate, what's the best way for him to do that if, say, he's a guy who you see at work but don't really ever interact with?