Trans

I think most people, both male and female, tend to act differently around men and around women, and that this comes from a lifetime of cultural conditioning. It's definitely not limited to male behavior, and frankly, associating it with "toxic masculinity" seems like the same mindset.

If you asking if gender determines how people interact, the answer is absolutely yes. There are so many ways this is true.

Some of their questions are...interesting, but I think the important thing to keep in mind here is that they're making an explicit effort to interact with you in the way you prefer, and it is probably be worth pointing out the comments that make you uncomfortable with them directly. They clearly want to make the effort to make you comfortable, so being direct with them would most likely be appreciated by them.

In regards to "is this normal?", I will say that, as a cis person, the line between "don't stereotype based on gender" and respecting gender identity can be quite murky and it can feel precarious to assume how someone wants to be treated after or during their transition. Everyone will have different expectations and wishes, so having discussions like this, though blunt and likely awkward, will hopefully lead to a better relationship overall.

It does sound like this friend cares about you, so I hope you're both able to address this constructively.

We live in a cisheteronormative society in which, yes, absolutely, the way someone's gender is perceived impacts how people interact with them.

I (trans man) generally don't treat my friends too differently based on gender, but there are definitely some differences between my relationships with women and my relationships with men. When I hang out with other guys, there's a lot more "dude", "man", "bud" in conversations (obviously). When I hang out with women, conversations about feelings and personal issues are more common, and so are hugs/embraces. This is pretty much entirely "code switching" for me, and not a case of me imposing that this is how relationships with a certain gender should work.

I should point out, though, that this is not 100% based on gender and gender only. It's largely about the personality, and we live in a world in which there is a strong correlation between gender identity and personality traits (see: gender roles and stereotypes), and so gender can often (but not always) act as a shorthand for that. As a counterexample, someone I know is an effeminate (cis) guy, and I'd say that our conversations and interactions feel more like the ones I'm used to with women.

Your question's made me curious; you appear to be binary trans (please correct me if I am mistaken!) Prior to making this post and having this discussion, what had the concept of passing meant to you? Was it purely about automatically being referred to with the right pronouns and terms (son/brother/etc) without having to say anything? Or was there anything more to it?

As a cis guy, this strikes me as exactly the opposite of toxic masculinity: he's trying to respect your preferences as to how you want to be treated, and in order to do that he has to know what they are first.

(I suppose in the ideal world, there would be enough out trans folks around that cis people would learn how to interact correctly in childhood, but that's not the case yet so we've all gotta learn somewhere.)

Also, you say in a comment that you thought he knew you because you hung out numerous times, but if he just found out you're trans and/or just became comfortable enough to broach the subject to ask these questions, then he clearly didn't know you as well as you think he did.

You're being a bit too sensitive I think. And also what's with cis bashing? I'm bisexual but I have trans friends who I would have similar questions for. They would never be offended by these questions or look for the malice in them. Why must you look at it maliciously because the person asking is cis (or you just assume they are cause they haven't told you otherwise, like people do with me).

Simply existing gets you labeled with toxic masculinity these days. I wish the term would die because it's been so bastardized that everyone uses it for anything they don't like about men. Use the term toxic femininity though and you get crucified

I had no idea thr opposite was a thing tbh. Personally, I've always treated boys and girls (or men and women) differently, I assumed everyone did this ? Not deliberately -as a matter of fact I've only noticed rather late, probably in my late teens. I can only surmise that it's social conditioning. Just like in your story, it became evident when I met someone who was neither obviously a man nor obviously a woman: I realized I didn't know how to act and was completely thrown off.
Lately I have come to observe that the sexual differences I thought were deep were in fact pretty shallow, and I found myself trying to "see" men as women and conversely, in an effort to break down this conditioning. But to be frank I thought I was doing something completely original... I would never have guessed anyone else had naturally attained this ambitious goal I set for myself !

It sounds like this person thinks your gender is your entire personality, and that by transitioning gender you are becoming an entirely new person. I think it’s normal that they turn to stereotypes and binaries to try and understand something they are unfamiliar with though. The “will we ever hook up” would absolutely throw me off if a friend I trusted said that, and that’s a whole thing to digest alone.

I’ll refrain from giving advice because it wasn’t asked for, but unfortunately yes. Lots of cis people need the boxes and stereotypes in order to interact with others in the “socially correct” way rather than making those determinations on a person by person basis. I think it’s part of the cisheteronorm standard that is still said quietly rather than out loud.

I mean, I exhibit those same differences in behavior, it's just that it's based on the person and not their gender. Some of my friends and I flirt, knowing we don't actually mean anything by it. Some want to hear my TMI stories and knowledge. Some would be incredibly uncomfortable with that. Some of my friends come to me with problems, wanting solutions, and some just want to talk about the problem. Some of these things are more likely to fall one way or the other based on gender, but everyone's different and treating you in stuff like this based on your gender instead of you is wack.

Should I wonder if we'll ever hook up?

I honestly have a hard time realizing that pan is not the default lol

I don't know about the average cis person, but as a cis man myself I find those questions a bit unsettling, and they suggest a world view that makes me quite uncomfortable. If these attitudes go deep, this person might be hard to remain friends with.

Definitely not purely a case of toxic masculinity. Gender roles and norms exist in all cultures, even those that were matriarchal.

We can debate all day of that's a good thing or not, but it isn't going away any time soon.

Mind you, the examples they gave are pretty lousy ones, despite being currently a part of general existence. The things they used are part of how women and men expect to be treated, and there's likely a majority that want those behaviors. No telling how many would want them because they genuinely prefer them, or because they've been trained to prefer them over time.

We all know that individuals vary, that there's no 100% possible with what a given person wants in regards to gender related interactions. There's just no way to exclude any of those as valid preferences either. Despite the obvious toxicity of the flirt/chill dynamic where that's the only two options and the default presence of sex needing to be figured out as excluded or not, those things do matter in heterosexual interactions. It isn't solely toxic masculinity and the patriarchal paradigm either, there's an underlying question of "what are our gender norms going to be?" that exists any time there isn't already a rigid cultural standard.

One thing I've noticed with friends that I've known before and after transition is the same confusion present here. It's as hard or harder to learn social expectations that you didn't pick up as you grew up than the physical experiences of transition. Part of that is that we learn a lot by going through puberty and navigating the hormonal shifts at a younger age when we're cis.

People that transition as adults seem to run into greater difficulty absorbing all the things we're expected to just figure out on our own during puberty. Part of learning to be a man is learning how to manage and control the behavioral aspects of testosterone. So many of the unwritten rules of being a man are driven by that need. The same is true for women, but the precise aspects differ to some degree or another (usually to a high degree).

I'm not saying any given behaviors should be a part of overall gender expectations, just saying that they exist and that means an extra layer of things that nobody seems to think of until they're involved in transition (either by going through it, or being close to someone that is).

Being real, I was in my thirties before I figured out that the whole "will we?" question isn't irrelevant, and can't be totally hand waved away intellectually. Doesn't matter what I do or believe, because there's plenty of times it'll arise in other people needing it answered. I had always thought that if you're around a woman or girl that's a friend, you just ignore the sex issue because it'll resolve itself over time and not need addressing. But that's not true. A lot of women need that addressed just so that they can relax around a male friend.

That's not just because men tend to assertiveness and/or aggression in sexual matters. Women can get wrapped up in their drives too, so its usually better to have the possibility of sex and romance (together or separately) worked out early on. It isn't like we don't sometimes want or need sex as a human interaction without it being something more, so even if you're both certain that romance is off the table, sex may not be, and that can come from either party, regardless of gender or orientation (I've been sticking to hetero interactions here because your post is about male/female interactions, but the same need to work out the issues exists with homogender friendship as well).

And none of that gets into the other aspects of gender related minefields that exist for someone transitioning. There's a ton of them that are hard enough to figure out at all, and trying to do so when you've never experienced the complexity of things directly is harder. Just the nuances of how men adjust their behaviors around other men they don't know is ridiculously complex, as one example that I've seen come up frequently. How do you learn all the little body language rules when you've never had to use them in a fluid way? It's as hard as unlearning them when transitioning to female. Having access to hormone treatment doesn't grant automatic understanding of such things.

All of that gets tangential to your ultimate question though. It is true that a shit ton of cis people see the world that way, and even more follow that standard because it is so engrained that you can't just discard it all without running into trouble.

Again, that's not about what should or shouldn't be, it's just an observation about how things are currently.