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You don't have to understand it and you may never do so. Accept..it(?) as it is and that's that.

Dont overthink it

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Other peoples pronouns aren’t about you. Don’t overthink it.

Call people what they like to be called. It’s not that hard to be a decent person. It’s one of the most basic forms of respect for a person.

I can tell that your heart is in the right place, and you want to be kind and respectful to your friend. You're doing great about using their pronouns. I agree with everyone else's advice to not worry too much about it, though I know that it's easier to respect somebody different from you when things "make sense". Here are a couple things to think about.

>“if they see know they’re girly, and are okay with it, why does it bother them to be seen as a girl? They LOVE skirts and makeup, and strives for the same feminine beauty as I do?”

Could you imagine a man who likes skirts and makeup? Maybe a man who works at a beauty studio and always has his nails done, or a man headed out to a gay bar. What about a woman who likes manly things, like jeans and short hair?

>My first thoughts were something along the lines of “why would they chose to live a kind of life that makes then feel that way?”

I'm assuming you're a woman, since you say you also strive for feminine beauty. Sexism makes your life hard. Does complaining about sexism mean that you don't like being a woman? If you could snap your fingers and become a man, would you want to? Even if it would make your life easier?

>I care very much for this friend, I want to be kind and respectful to them, and this is coming from a place of wanting to understand them better. Since I wasn’t there when they decided to make this change, we’ve never really talked about it at all.

I've got some simple advice. Invite them to hang out and chat in a space where you both can have a candid but casual conversation. Then just ask them to tell their story. Your own words are the opening.

"I want to be a supportive and good friend. Would you be comfortable sharing your story and journey with me?"

Then listen

You could think of pronouns like this;

Imagine that you have a friend you've known since you were little. You've always called him "Johnny". You're now both in your 20s, and he's asked you not to call him "Johnny", but to call him "John". You might slip up now and then and accidentally call him "Johnny", but so long as you correct yourself and apologise, you should be fine.

Don't ever be afraid to ask for clarification, this shows that you want to respect the person and call them by what they want to be known as.

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That’s all I want. I tried to ask about itlast time we hung out, and they instantly seemed so anxious and gave me such short simple yes or no replies, and didn’t try to expand on anything I asked or they answered. I just… I don’t know how to start that without making them feeling like they’re just being questioned.

Gather your friends who knew this person pre-transition, and tell stories about this person using their correct pronouns. Don’t let your stumbles stop you from self correction. Don’t overly apologize in the conversation with your other friends, in the same way you wouldn’t with your friend with new pronouns.

It sounds like you are a wonderful and caring friend!

But you missed the chance to listen. If they didn't expand when you asked, that's what you need to hear. Let go of worrying about the past until they open up on their own.

Instead just be present with them as the good friend you are