Well, haven't constantly updated this, but I am now out to my immediate family (mom, dad, brother), all the girls I know and a couple guy friends (jncluding my roommate).
Two things have been constant in every case. First, nobody ever guessed or suspected, even the ones I was positive would have figured it out. Second, nobody cared. Not one person even seemed slightly uncomfortable about it, even for a second. Everybody has been beyond supportive and if anything I feel like most of the relationships that I had worried would suffer are now closer.
I am also out to the other gay man in my office, I wanted his opinion about how our office would handle openly gay men. He says he has never faced any sort of discrimination (and he said he would absolutely tell me if he had), and that everybody is supportive. I'm not planning on coming out to the office or anything like that (I just don't think it's appropriate), but if anybody asks about dating girls or something I'll be honest with them and let the work gossip mill take care of the rest.
So yeah, essentially I'm out now. It feels good and was infinitely easier than I expected it would be, but that's probably just lucky on my part.