I actually did mention the wig option, but he seemed hesitant about it, though I couldn't figure out for sure why from what he was saying. He's feeling very hesitant about doing anything that might be perceived as overtly feminine, anything that might draw too much attention. I don't know if scarves would be less so than wigs, but they might feel less like he's trying to "pass," with the potential for embarrassing failure to do so. Maybe wigs seem too much like he'd be "pretending" to be a woman?

I think having both (wigs, scarves, and maybe some other possibilities, too) as options might give him some room to consider what might feel most comfortable to him. Right now he doesn't seem comfortable with the current situation, but doesn't seem entirely comfortable with changing it, either. It's a pretty scary prospect, I imagine. He's in a tough situation, but I hope it will get better with time, support, and experimentation to see what works for him personally.

He said that he enjoys looking more feminine when he's alone at home, but then gets an unpleasant jolt when he sees himself in a mirror, becaus he doesn't look the way he feels (and doesn't like the way he looks). I think wearing the wig at home is a great idea, and I'll suggest it next time I see him. It might make those mirror glances less jarring, and he won't have to worry about anyone else's reaction to the wig.

As for how serious he is, in our conversation today at one point he waffled a bit and awkwardly said he "isn't quite sure about this whole thing." I'm trying to take him at his word about that, but the fact that he has chosen to take hormones (apparently he has been taking them for a year now, though he did not develop any obvious physical changes until very recently, and he hadn't come out to me or to the community at large until the last month or two) and also the fact that he seems to be working fairly hard to overcome his fear of people judging him so that he can look and behave the way he wants makes me think he's more certain than he says. I'm guessing that he's shying away from defining himself (as transgender, as female, whatever) because of all these fears he has about what it will mean for his role in society. But that's just my guess, of course, and I have no idea what's really going on inside him.

Thanks for the suggestion about wearing the wig at home! I think that might really help him.

My closest friend (aside from Shannon, of course) is an MTF woman, and I've also spent a fair amount of time with some of her friends who are also MTF, but they are all fully transitioned and have been for years. When I first met Lisa (the close friend), she was out to everyone except her employers/coworkers, and so -- depending on who was with us -- she was sometimes called Tom and sometimes called Lisa, sometimes dressed in more masculine clothes and sometimes in dresses, but she was completely out to me and our group of friends, she was living most of her life as a woman at that point, and so I didn't know her when she was going through this kind of struggle for identity. I'll ask her if she has any ideas about how I might help this other friend, but I assume that -- just as every person is different -- every trans person's transition is different, so what helped Lisa might not help someone else. Still, she's very educated on the topic, so she may have some helpful advice.