I kinda wish I had the guts to just do it all at once. So far I'm doing it in steps. My local friends were the first. Then a handful of distant friends. And one family member.
And I've decided to tell no one else until I'm farther along in my transition.
My roommate still doesn't know. Although he has caught me in girl mode three times now - the last of which he just turned and faced the wall until I left the room. So, I don't really think he wants to know. Fine by me, so long as he continues to be an ostrich about it rather than violent about it.
I do want to tell my best friend, but, he's currently in China for school, and email and text message are the only means of communication we have, and I feel like he deserves more than some brief text or a very confusing and emotionally charged email about it. But, at the same time, I'm going to be picking him up from the airport in June, and I'm guessing HRT will have made a lot of very obvious changes by then, so, he's in for a surprise unless I can find another way of telling him sooner. This, sadly, has put some strain on my local friends, as they're friends with him too, and they don't want to out me to him before I've had the chance to talk to him about it.
My employer will be the last to know, ideally. Although, I nearly got caught by a coworker in girl mode at a gas station this morning. Damn small town...