Oh, right. No, I, myself, am male, in both assigned sex and gender.
Ah, in that case my advice is probably pretty off base.
Mine too.
“Do I look pretty?”
“Dude, whatever! Jesus!”
Sorry I missed this thread; I am very busy lately. If you have detailed transgender or transsexual questions and don’t want to bump the thread, drop me a PM or mail. I’ve done decades of research on the issue, interact daily (hourly sometimes…ladies, put down your phones once in a while!) with the TG/TS community, and am a counselor, mentor and protector of TG/TS women in real life. And I have other direct experience as well, especially with self-image freakouts.
However, to try to answer things in here…it’s a minefield of an issue, especially if the transwoman is early in the transition process, and especially if, to be blunt, she just doesn’t pass.
To some extent it’s the same basic thing as telling a cisgendered woman your opinion on her looks, except the cisgendered woman isn’t a fragile butterfly of a new woman with no self-confidence and filled with a vague terror at their place in the world.
I find many (most?) people beautiful in some way, and I can tell them that. You can also make “compliment sandwiches”, where you say “Your hair looks really good, maybe you need a little less foundation (unsaid: because you look like an Aunt Jemima box exploded on you), but you’re working it!”
Since I also study women’s fashion in detail (and get asked to consult on clothing a bit), I can often deflect a question into a positive comment about clothes.
Another thing to do is think if the transwoman looks like another woman you know, personally or otherwise. Transwomen have gone through a process, an epiphany if you will, of accepting that the female mind inside them is real, and they are sometimes continually grasping for validation of that. So if you can honestly say “you look like a girl I knew in high school”, with no judgment on whether said girl looked good or bad, that would be very much appreciated as it’s validation of female appearance.
I mean…from talking with untold transwomen and reading innumerable books and papers, and personal experience of course, transwomen first and foremost want to look and be perceived as female, and looking pretty is secondary. So if she is clearly doing well presenting as female, even though she may not be attractive, focus on that first part.
And honesty should be appreciated. A transwoman who is probably one of my best trans friends wore a platinum blonde wig for the first few times I met her, which was expertly done and which fooled me completely into thinking it was her natural hair (not easy to do, I brag). When I complimented her on her wig, her reaction was an icy and self-loathing:
“It’s a WIG, Una. My real hair sucks. I’m really surprised you couldn’t see that.”
and my reaction was:
“How could I? Do you know how hard it is to make a wig look good? Women try for years and years and will never be as good at using a wig as you are. You have a natural female talent for it.”
See what I did there? Every word is honest, but I emphasized that she had a natural female talent in using a wig, and emphasized that many women do in fact use wigs (especially at my age, says Old Aunt Una…)
However, please note that probably half of new transwomen are in very unstable or metastable states due to the tremendous and overwhelming wave of societal and personal issues involved with coming out, as well as the tremendous mood-modifying impacts of estradiol. You may say nothing wrong whatsoever and still face a freakout. If that happens and you know you did nothing wrong, please be patient with your friend and don’t take any recriminations towards you personally. You cannot imagine the combination of terrifying lows and dizzying lows which come with the start of transition, especially if they are a transsexual on a high hormone regimen. Eight hours of dancing-around-the-room happiness can be followed by an hour of hiding in bed with box of Kleenex. New transwomen need a lot of help and support to survive, believe me, I really, really know this.
I just want to mention how extremely great that post was, Una.