Well to make things even more interesting, I met my friend's sister's new beau. A manly-man, as far as appearance goes. I was keeping my opinion reserved until I actually met him. A few weeks ago I noticed my friend's sister post a photo of her boyfriend letting her pain his toenails pink. I was intrigued. The other commenters were lovingly teasing him, and I didn't want to do that, not having met him; instead I wrote, "How cool is that that he's not afraid to challenge gender norms?"
So last Sunday I met him in person & even though I felt a bit skeptical before hand, I instead found that I liked him before we even said a word to each other. So I felt at ease, and as an icebreaker I asked how long the pink nail polish managed to stay on--he said it came off the same night after he noticed people staring at his feet at Wal*Mart. Which I thought was funny, 'cause, you know, it's WAL*MART. He said something about "the things we do for women."
Somehow that turned into a discussion between him & his girlfriend, that may not have been intended for my ears. But I was right there in the room, ya' know? He told her that he used to dress up as a woman for Halloween (and that he was damn good at it, too, lol). I was intrigued both by his saying so & his girlfriend's accepting curiosity about it. When he & I were alone in the kitchen I asked him casually but quietly, "Would you ever do that again? Dress as a woman for Halloween?" He unhesitatingly said, "Sure; I got no problem with that", then said it'd be harder because he's bulked up since he last did so.
I left feeling good about him, and better about the human race in general. I know lotsa' cruel & nasty stuff is yet to be eradicated, but his comfort with himself in pushing the gender boundary leads me to think he's at the very LEAST trans* friendly. How refreshing.....another win.

~v.