Questioning my gender after years. Help!
Posted: Sun Oct 11, 2026 7:58 pm
Hi everyone! I'm a late 20s/early 30s lady (?) posting because I'm finding myself deep in the gender whirlwinds and would love some support or advice.
Long story short, I was a lifelong tomboy--it was pretty lowkey when I was a young kid, but as I got older I started to really dislike wearing and being "too girly"; men's clothes, hiding my hair under hats until I could cut it, presenting pretty masculine was a strong preference of mine. As I got even older, I started questioning my gender; "woman" didn't really feel right, so I was experimenting with transmasc/nonbinary identities, mostly with my presentation, nickname, and pronouns with some friends--no hormones or surgery. A few years after that, it kinda fizzled out. I felt awkward in my masculine clothes, and branched (a tiny bit lol) into femininity. I realized I liked my birth name, my pronouns didn't bother me, and I didn't feel a need for hormones or surgery.
Fast forward a few years, to now. My "feminine" era hadn't really panned out--part of me wants to be really cute and girly, but the other part of me loves cargo pants and deep pockets and work boots and hoodies, so I didn't get super far. But I know plenty of masculine cis women, so I figured it was fine. But there's been some other stuff on top of my feminine-failure-to-thrive; still getting a little gender envy from men, especially deep voices sometimes, wanting a penis and kind of getting curious about bottom growth with T. I gained some weight and it's made my boobs more prominent, and I don't really love how it looks in T-shirts, though I can't tell if that's cosmetic or gender related.
But yeah. Last night it all hit me that, yo, maybe I'm not totally "past" my gender experimentation era. Unfortunately, questioning phases = "freak out" in my brain, so just like I did the first time I questioned my gender, I have started freaking out. Questioning my whole reality, honestly. Like, do I want to be a man? Have I always wanted to be a man? Would I actually enjoy the realities of being a man? But then, I've also been doing some sexting/NSFW chatting (I don't really have any other sexual or relationship experience besides that), and being seen as a woman and using my "female" body parts never bothered me there--what's going on with that? Do I need to change my name? Does it bother me? Do I need to get on T? What's the end goal here? Why was everything fine two weeks ago and suddenly I'm wondering if my whole life was a lie? Can I just ignore this and resume my regularly scheduled woman programming? Do I want to do that?
And then, to compound on all of this, I recognize that I've also been having a tough time with body image and self-concept in general. I'm slightly on the taller side, definitely on the heavier side after some recent weight gain (stress eating :/ ), and I've always had big hands and feet. On top of that, I also have been basically buzzcutting my hair because I have a scalp condition that does better when I don't have a lot of hair. I haven't really loved how I look recently, and I think part of what makes that even harder is that there are a lot of things I can't change about myself, and other things that I just haven't really bothered to, that don't fit into the classically "feminine" box. So am I actually having gender-question-y thoughts, or is this my brain just deciding that there's no point in ~trying to be a woman~ because I'd probably look better/be "more congruent" as a man?
So, yeah. Any advice? Especially tips on calming the gender-anxiety, lol.
Long story short, I was a lifelong tomboy--it was pretty lowkey when I was a young kid, but as I got older I started to really dislike wearing and being "too girly"; men's clothes, hiding my hair under hats until I could cut it, presenting pretty masculine was a strong preference of mine. As I got even older, I started questioning my gender; "woman" didn't really feel right, so I was experimenting with transmasc/nonbinary identities, mostly with my presentation, nickname, and pronouns with some friends--no hormones or surgery. A few years after that, it kinda fizzled out. I felt awkward in my masculine clothes, and branched (a tiny bit lol) into femininity. I realized I liked my birth name, my pronouns didn't bother me, and I didn't feel a need for hormones or surgery.
Fast forward a few years, to now. My "feminine" era hadn't really panned out--part of me wants to be really cute and girly, but the other part of me loves cargo pants and deep pockets and work boots and hoodies, so I didn't get super far. But I know plenty of masculine cis women, so I figured it was fine. But there's been some other stuff on top of my feminine-failure-to-thrive; still getting a little gender envy from men, especially deep voices sometimes, wanting a penis and kind of getting curious about bottom growth with T. I gained some weight and it's made my boobs more prominent, and I don't really love how it looks in T-shirts, though I can't tell if that's cosmetic or gender related.
But yeah. Last night it all hit me that, yo, maybe I'm not totally "past" my gender experimentation era. Unfortunately, questioning phases = "freak out" in my brain, so just like I did the first time I questioned my gender, I have started freaking out. Questioning my whole reality, honestly. Like, do I want to be a man? Have I always wanted to be a man? Would I actually enjoy the realities of being a man? But then, I've also been doing some sexting/NSFW chatting (I don't really have any other sexual or relationship experience besides that), and being seen as a woman and using my "female" body parts never bothered me there--what's going on with that? Do I need to change my name? Does it bother me? Do I need to get on T? What's the end goal here? Why was everything fine two weeks ago and suddenly I'm wondering if my whole life was a lie? Can I just ignore this and resume my regularly scheduled woman programming? Do I want to do that?
And then, to compound on all of this, I recognize that I've also been having a tough time with body image and self-concept in general. I'm slightly on the taller side, definitely on the heavier side after some recent weight gain (stress eating :/ ), and I've always had big hands and feet. On top of that, I also have been basically buzzcutting my hair because I have a scalp condition that does better when I don't have a lot of hair. I haven't really loved how I look recently, and I think part of what makes that even harder is that there are a lot of things I can't change about myself, and other things that I just haven't really bothered to, that don't fit into the classically "feminine" box. So am I actually having gender-question-y thoughts, or is this my brain just deciding that there's no point in ~trying to be a woman~ because I'd probably look better/be "more congruent" as a man?
So, yeah. Any advice? Especially tips on calming the gender-anxiety, lol.