Trans-Man Stephen Dabby’s Origin Story

By Beatrice Tolan   |   July 21, 2026
Meet Stephen Dabby

In a man-cave bar in the L.A.’s Art District, I watch the World Cup… but I’m really waiting for the Pride event, a packed setlist of queer musicians, to set up next door. I’ve instructed my buddy Stephen Dabby to arrive an hour early for our chat. Stephen is a charming studio artist with a bright smile, bushy beard, and boisterous nature. Though we both grew up in Santa Barbara, it’s our first time hanging solo. What better conversation to break the ice than to discuss his transition into a man? 

Stephen graciously recounts his transition process, expounding on its highs and lows while dispelling common misconceptions. He also provides critical insight on how allies can support the trans community in the particularly scary time we find ourselves in. 

Q. When did you first come out as a trans man? 

A. Well, I first came out as gay at 14 or 15… I swear I came out like two to three times. But I was still presenting as a female. The second time I came out as genderfluid when I got voted as prom king.

Were you presenting as masc (masculine) at the time? 

Yeah, I had an undercut; that’s how it starts. And then I came out as trans at 21. That was definitely the most nerve-wracking one. 

How was that process?

So, I’m in my third year at Sonoma State University as a woman’s and gender studies student. And I’m like, holy shit: I’m actually a trans man. I guess I’d always known this. Growing up, I’d always been a tomboy. My parents never pushed gender on me either, so I never questioned my gender because it was so fluid anyways. And I always went by like an abbreviated version of my dead name [name before transitioning] because it was more affirming to me. At the time, I didn’t really understand what that meant for me. 

You didn’t attribute it to gender euphoria? 

Yeah, I just knew it felt good. And I didn’t question it more than that. Anything more than questioning would bring me to a really uncomfortable place. When I thought of trans people – and this was my internalized transphobia – I thought about sex and genitals. But once I started taking women’s and gender studies classes, I really peeled back the societal and patriarchal parts of why I was thinking that way. When I realized what was going on for me, I left school because I needed to start T [testosterone]. It was in a pretty serious way. 

How would you describe gender dysphoria to somebody who has never felt it?

It’s like you’re putting a puzzle together, and it’s the most beautiful puzzle you’ve ever seen… but the pieces that have the most detail in it are missing. Coming to the conclusion I was trans was like finding all of those last pieces in one bucket and knowing exactly where they fit. I sat my parents down and started crying. And I finally got it out. My dad was like, “Why are you crying?” And I was like, “I’m scared.” And he goes, “If you told me that you were a zebra, I’d go out and find the stripes for you.”

How would you describe the experience of transitioning? 

With this answer, I will take into account the privilege of now passing [appearing cisgender]. People don’t mistake my pronouns. But in the beginning, I wasn’t passing. It was a lot of weird looks, people misgendering me, and hostility. It would be stupid to not say that in my transition, I tried to follow the path of least resistance. There’s all these fish going downstream, and then there’s one salmon that just turns around like, “Okay, I’m going the other way!” That’s kind of how I saw my transition. People are not gonna be going with me in the current, but that’s my path to exist, and I just got to fucking do it. 

Was it interesting to reintroduce yourself to people who knew you before you transitioned? 

I never wanted it to be a big deal because I’m exactly the same person. The only thing that’s different is the way I present myself. Pretty much everything except for my soul has changed.

Yeah, that’s interesting. I sometimes sort of see my outer self as my avatar. And as I get older, the things I change about my avatar are what I would have naturally been doing if there wasn’t a societal expectation not to. 

That’s actually a great way to put how I feel being trans, especially in L.A. I feel way more comfortable experimenting with my femininity. I have fully accepted individuality within myself because it’s such a big town. I’m not seeing the same people twice. 

And to your point about leaning into femininity: I think a lot of people assume that if you’re a transman, you’re aiming to look like a cisman [non-trans male]. We are hopefully entering a place where a man, regardless if he is cis or trans, can lean into femininity, can wear skirts, can do whatever the fuck he really wants. 

Exactly. It’s that rebellious expansiveness that I’m leaning into, wearing tank tops and crop tops that I would never do before transitioning. 

How do you feel when people say something to the effect of “I don’t want to offend you” or “I’m nervous about saying the wrong thing”? 

To me, I am such a forgiving and open person. I can’t speak for anyone else. But you know what? We can talk about it and I’ll tell you if it’s offensive, which it rarely is in the end. There’s just this fear of saying the wrong thing, getting canceled, or having someone’s perspective change.

With recent laws targeting the rights of transgender folks, how can people who see themselves as allies make trans people in the community feel more welcome?

Support the Santa Barbara Trans Advocacy Network (SBTAN)! They were my first safe haven when I moved back to Santa Barbara. And the people who aren’t trans, I feel like they should do their own research. If I could, I would have everybody know a trans person. If you personally know someone who is trans, you build empathy and sympathy. You’re like, “This whole time I thought being trans was A, B, and C, when really, it’s just this person that I adore.” Even if you’re scared, ask questions. Lean into the uncomfortable. Don’t be afraid of the uncertain, because if we all were, then no one would be trans.  

 

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