I don’t know very many trans people in real life, but it’s something that I wonder about whenever having an interaction on a personal level. I don’t mean this to sound invasive or creepy. It’s an honest question from a person who simultaneously wants you to feel as free and welcome as I can help you to feel living on the same planet as me, while also having absolutely no paradigm for what it feels like to be a transsexual person. Do you tend to appreciate it when someone comments positively on your looks or clothes, either with or without reference to the fact that it’s sometimes somewhat apparent that a transition occurred at some point, or do you prefer that it goes mostly ignored like it does most of the time for cis people? Does it feel like a patronizing participation medal, or kinda validating? On one hand, I know that if I complete a project, it feels good if someone comments on it without me pointing it out, and asks questions about how I did it, and I’m likewise happy to acknowledge the amount of work and bravery that a trans person has put into themselves, but you also have other stuff going on in your life, and I don’t want to make it weird by making you feel like that’s the only part of you that anyone notices.
For clarity: this is on the premise that it’s done with social awareness and tact. I don’t mean complimenting someone by saying “You really do look like a guy.” I’m more asking about something along the lines of “I like your dress. That’s awesome!” With the extra “that’s awesome.” part, being verbal shorthand for: it’s awesome that you’re being honest enough with yourself to wear it in public, and I respect it. Thoughts?
You have good intentions, so that’s a good starting point. I think the trick is to not overthink it to much. You don’t have to overtly prove that you are safe and supportive. And as you already realized, you don’t need to call attention to the person being trans.
I play tabletop games at a local gaming store at least once a week and there are often a half dozen or more trans people there playing games. My friends and I just talk to them the same way we would talk to anybody else in the store. That doesn’t mean we’re all exactly the same. Some of us are bubbly and extroverted, some of us are more reserved and introverted. But the key thing is: we don’t change to some other “mode” of interaction when the person we’re talking to is trans.
So if you normally casually compliment people on their fashion choices, etc, and you can do it in a nonthreatening socially smooth way, sure, I think that’s fine. But if you are being “extra” just because the person is trans, and doing some kind of role play you normally wouldn’t…don’t do it.
I hope that helps.