Heavens, a lot of righteousness in this thread.
I’m going to… well, I’m going to answer this the way I would. I saw the answer before OP clarified, and I’m giving the same answer I would before, but maybe with a bit more details.
I am cis het, and present as such. I’m also middle-aged, so I predate the current increased visibility of trans people. Which means, you know. I’m the group OP is likeliest to be worried about, if they meet me in close quarters.
I have just OK liberal credentials with regard to transgender issues, I guess. I have learned a lot in the past year from being on Quora. I number several transgender and genderfluid people among my online friends, and I make a conscious effort to be supportive of them and to respect their boundaries—which I’m only finding out about now. I don’t volunteer with any transgender groups, and I don’t know any transgender people IRL; so yes, I could do more. But I guess ideologically, I’m aligned with most of the people who’ve responded so far.
Would I feel awkward talking to a transwoman at close quarters, who obviously does not pass?
Yes.
There’s some clear reasons for that, and I’m going to take the time to think them through. OP deserves as much.
First, I don’t actually know any transgender people IRL, so it would be a novelty. Not something to be proud of, but there you go.
Second, I anticipate that, with someone who obviously doesn’t pass, from a group that I have had minimal IRL contact with, I would experience a bit of the Uncanny Valley effect—the freakout people get when they see someone who doesn’t quite match their preconceptions of what normal is.
Of course one’s preconceptions are preconceptions, and nothing to be smug about. Of course preconceptions are battered down by more and more exposure to different images of how people do gender. Of course heteronormativity (cis-normativity?) is a thing.
And people unaccustomed to seeing trans people who obviously don’t pass (can I abbreviate that? TPWODP?) are going to stare a bit more, and feel awkward about the novel encounter, even with all the good will in the world. That’s not an excuse, but it is a thing that you will run into.
But you know, I’ve had that experience of awkwardness before. I’ve had it when I first moved to Melbourne, and saw Asians for the first time. If I stared every time I saw an Asian Australian in Melbourne, I’d never get anything else done; but I did stare at the age of 12. I’ve had that experience when I first met Australian Aboriginals. I’ve had that experience when I first met a butch lesbian.
And I got over it, and in fact I got over it within the time frame it would take me to hypothetically get stuck in an elevator with OP. My best friend for a decade was a butch lesbian. (Well, baby dyke, really, but I didn’t know the distinctions when I first met her; after all, I was unfamiliar.) I was bantering and singing with the first Australian Aboriginal I met within a half hour. The guys I’ve kept in touch with from high school are Asian Australians.
OP, you’re right to be worried about how people will interact with you. Some will not get over their unfamilarity. Some will be assholes. You need to be prepared for that, and you need to seek advice of people who’ve been on the receiving end of it, not just the dishing out side of it. Jae Alexis Lee for example.
But, if this cis het guy can say one positive thing: I stumbled across the transition timeline that my friend Nic posted online. Literally stumbled, actually; she was surprised I found it. (But hey, she did post it publicly, and gave me the address to her blog.)
And what others have said about their transition, well, it was true to see there too. As she transitioned, the light came on behind her eyes. The corner of her lips turned up. The confidence was visible. The joy in experimenting with different kinds of makeup was obvious.
She’s more beautiful now than before: not because there was anything misshapen about her as a boy; not because she is aligning more to heteronormative norms of what a chick looks like. She’s more beautiful now than before, because she’s visibly happier in her own skin than before.
And you know what? Those who do not willingly blind themselves: they’ll see that too.