I Started Transitioning in My 60s: I’m Happier Than I’ve Ever Been
7 min read | Jun 2022

I Started Transitioning in My 60s: I’m Happier Than I’ve Ever Been

Living authentically has me feeling like I’m in my 20s again.

Dana Paige / Baby Boomer / Progressive / Undisclosed

I’m 62 and I’m trans.

I've always felt that something was up, but I grew up in the ’60s and ’70s, so there was no trans path. There weren't resources, and there weren't doctors, and there wasn't information. I would read in Life magazine about somebody going to Germany to have a surgery or something, but really, for me, it just didn't exist. It wasn't like I had trans friends or we had someone in the family like that. There were no role models. 

As far as I knew, there were just the two paths, where you were either a heterosexual man who likes women or you were gay and you like men. And that was it. I kept wondering if I was gay, and I kept going no. Being gay never fit for me. I just never felt that way. But I was lucky enough to have gone through a lot of therapy and human development and done enough internal work that once I realized I was trans, I was able to be OK with myself.

There wasn't a specific moment for me when I realized it. There was a five-year buildup, and then suddenly, there was this crescendo of things that happened. It had to do with my doctor saying my testosterone levels were too low and he had to boost those up. It had to do with a couple of things going on in my life. I'm sure COVID had something to do with it, just being inside and being with yourself so much.

“”

I Wasn’t Comfortable With Myself, and I Needed to Do Something About It

I started transitioning in December of 2020. It was the weekend after Thanksgiving, right after the election. It was a very tumultuous, kind of horrific time for everybody. We were all locked in the house. The virus was running rampant. I knew something was going on with me, and I knew that I needed to get to the bottom of it. I never was comfortable with taking pictures of myself. I wasn't comfortable with my voice (and I’m still not that comfortable with it). I just wasn't comfortable with me. I was proud of myself before. I was smart, I'd accomplished a lot, but I was putting forward this name and image of someone who truly wasn't in alignment with my deeper sense of self, even though I didn’t realize it.

I started taking a deep dive into myself. It’s like I went into a dressing room, and I was trying on clothes, trying to find the identity that fit. Was I gay? I had tried on that suit, and it just never felt right to me. Then, I put on the trans outfit, in my mind's eye, and I just knew instantly. This has been it for all these years, and it was something I never even considered.

It was a revelation. I stayed up all night, not sleeping, typing away on my iPad. I start going back in my life and typing out incidents that I couldn't explain, things I had done, things I had thought, things that had happened, incidents from my life that just didn't really fit. It was pages and pages, going all the way back to college, to roommates, to being a kid trying on my mom's clothes. Everything I looked at, it was like, “Oh my god, this is what it's been all along.”

After that night, it wasn't a question of whether I was trans or not. I saw two pathways going forward: one that I had been living and the other that I could move to that felt more authentic to who I really was. It was a kind of a no-brainer, as long as my wife was OK with it. If I could go through it and not just pick up and leave, I was going to do it.

My wife and I sat down and I disclosed to her what was going on for me. And she looked at me and she said, “Oh, well, I guess that's what we're doing now.” She had no clue what being trans was or what it meant to have a husband transition. And I actually didn't know anything about it either, other than maybe things you hear from Caitlyn Jenner.

I Didn’t Know Anything About Transitioning When I Started

So I started transitioning. I was pretty much determined to be on the fast track because I didn't want to be in the awkward early stage for very long. There are trans people who go in a variety of different pathways. Everybody has their reasons for choosing theirs, and none of them are any better than the others. For me, I wanted to get through the uncomfortable part fast. So it took me a year to get to a place where I felt comfortable. Now I live as a woman all the time, and this is just who I am.

The process of transitioning is hard. I’ve had facial feminization surgery and breast augmentation. I've lost weight and learned how to take care of my skin and do my eyebrows and nails and just the million things that women do. I’ve spent a fortune, and we spend time and pain and emotional turmoil, just to be approved of and accepted. But now that I feel I'm on the other side, I wake up and live one thousand percent full-time female. When I go out into the world, I don't think twice about it anymore. Ever since I've been transitioning, there's been a joy and a comfort and a satisfaction with who I am that I'd never had before.

Regret is the one thing that’s been really tough. I wish I had transitioned when I was in my teenage years. I think about that all the time. You think about how you'd look and how you'd feel and just going through those years of my life that way, as my authentic self, would have been great. I see stunning trans women, and, of course, I want to get as close to that as I can. The older you are when you transition, the more surgeries you need to sort of counteract the puberty and all of the testosterone that's driven your body to build in a certain way. But I also know that if I had transitioned earlier, I wouldn't have the relationships I have now. It is what it is. And what I need to do is make the rest of this super exciting and successful for me. 

My wife and I have always had this soulmate-like relationship. When I told her that I wanted to transition, she knew nothing about it. I had a number of conversations with people on Reddit about how to talk about it with her because it’s this self-centered understanding that I'm going through. This is my journey. It’s been exciting for me to transition with her, but every moment that’s been exciting for me was another moment where the old person that I was, was being pulled away from her. My wins were her losses. 

And all of our friends, because I was going through the transition, rallied around me, and she didn't get a lot of support because you don't think that the partner needs attention too. But they're going through deep, deep work. They've got to decide, do I still want to be with this person? Do I still want to have this relationship? In her case, she had to ask, can I be with a woman? This isn’t what she signed up for. Attractive, to her, is Cary Grant, and all of a sudden, I'm wearing bras, and I'm wearing dresses, and I'm going shopping, and all of that stuff that happens starts to eat away at what she knew.

“”

Transitioning Made My Marriage More Complicated but More Satisfying

So we've had to really create a new kind of relationship, and it's been very difficult. There's been a grieving process on her end, over losing her husband. She had to go through all the stages of grief. Now we're at the stage of acceptance. One of the best things that she's done is she found a therapist who specializes in spouses of trans people. She needed to go through the same level of work as I did, just in a different way. And the more she did, the better our relationship became.

It takes a while for people to come to terms with their loved ones’ transitions. They’re dealing with their own stuff, right? I think people who are transitioning need to allow their significant others time to come to the table and accept them, in a sense, not that it's my responsibility that my wife accepts me, but I have to give her time and space to go through her process and not expect her to be there immediately. My father was a perfect example. He was never gonna say “she” and “her'' and call me by my new name ever. And now he does. I was like “OK, so listen, you've known me my whole life as a certain thing, and you're welcome to continue to use that if you want to. But as I transition, I don't look like that person anymore. I don't really act like that person too much anymore.” So now it doesn't line up anymore for him to call me that, and he just automatically is now moving to my preferred pronouns rather than me forcing that. It felt very natural. 

A therapist told my wife, “Well, you have a 17-year-old girl on your hands now,” because transitioning is so like a second puberty. I don’t feel 17, exactly. But maybe 27. I’m always like, “Let's go out. Let's go do this. Let's go do that.” And she's like, “Really? I don't want to do any of that.” But to me, it's all new and exciting and fun. I'm looking for those experiences that she's done a million times. Like New Year’s Eve. When you're in your 20s, you're like, “Yeah, let's go crazy.” And then eventually, you realize how terrible New Year's Eve is, and you're like, “I’d rather go to sleep before the ball even drops.” But now it's a little different. It's like, “Can I go someplace with a ball gown on? Can I wear this? Can I wear that? Can I do this? Can I do that?” There are so many things I’ve done a million times before and now it's all new and fresh and exciting.

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