How do I start a conversation with someone?
You have to have a hook — something to talk about once you get the first hello out. If you’re sure he knows who you are, and you see him wearing something particularly notable one day it probably wouldn’t be too weird to email him about that. You know, a “hey, I saw you had on a Penny Arcade shirt! Teh awesomez! Have you ever been to PAX?” Or, you know, whatever. The key is to find something that will be an icebreaker and give you an excuse to compliment or ask about it. But also something that will give you a follow-up question, so he doesn’t just tell you where he got the shirt, shoes, cubicle toy, etc. If the initial contact goes well, now you have an excuse to talk to him when you see him around the building. Pretty soon you’re that girl he talks with about foo. Then you invite him to wait for it… bar. Basically, what you’re trying to do is get to know the guy and let him get to know you so that there’s something between you other than “OMG, he is teh hott.” I met my current boy
