Monika: Growing up in a conservative, evangelical environment, what were the first messages you absorbed about
gender, and which of those messages took the longest to unlearn?
Denise: The messages were very traditional. Like Mayflower-era traditional. Men were supposed to be masculine, women
were supposed to be feminine, and anything else wasn’t okay. They believed being a rainbow was a choice, and it was
the wrong one. My parents were conservative even by evangelical standards.
I knew I was different by four. When I was ten, I saw trans people on Maury and realized I was trans. I didn’t tell
anyone, but I knew the deal. My family believed it was something you buried and eventually it would go away. And if
it didn’t, have fun in hell. So I learned how to fit in. I played sports, worked out, had girlfriends, became a professional wrestler, and
eventually got married. I genuinely loved wrestling and many parts of that life, but I was also trying incredibly
hard to be the person I thought I was supposed to be. When I came out to my parents, they had no idea.
The hardest thing to unlearn was the belief that being different was wrong and made you a bad person. I spent years
worrying about what people would think if they knew the real me. Eventually I realized their response doesn’t affect
my life in any way and says far more about them than it does about me.
Monika: When you came out, did your mother embrace you as her daughter? And do you feel any connection to her in
the way you look, carry yourself, or even in your style and mannerisms?
Denise: No. My mom was really worried that people would see me being trans as a reflection of her and think she had
been a bad parent. We fought a lot, and it bothered me that she made my identity about her. She never introduced me
as her daughter unless it was to some single neighbor she was trying to marry me off to. After she died, I posted an old picture of her and several people told me how much I looked like her. That surprised
me because growing up, I was always told I took after my dad’s side. Brown hair, brown eyes, tall. I would have killed to be 5’7” and 130 pounds, though. As much as we fought, I do miss my mom. She passed away in 2018. I had a pink lotus flower with her initials
tattooed on my wrist a month later.
Monika: Do you remember the first time you met a transgender woman in person? What was that experience like, and
how did it make you feel?
Denise: Yeah. It was at a transgender support group meeting in Cincinnati, the first one I ever attended. I remember
meeting an older trans woman who had been married for 39 years and came out after her wife passed away. All those
years together, and she never had the courage to share who she really was with the person she loved most.
|
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“I wrote constantly and did
around 500 sets in 14 months.” |
Her story changed my life. In that moment, I realized I didn’t want that to be my story. I didn’t want to look back
30 years later and realize I had missed the opportunity to live a full life because I was afraid to be uncomfortable
and lacked the strength to let go of relationships that had conditions. When I came out, my ex and my mom both asked me, “Who could ever love someone like you?” It hurt so much, and those
words still haunt me. But the person I am now is the person I always dreamed of being. My relationships and
friendships are deeper because they’re real.
Monika: Many people experience transition as both liberation and uncertainty. What part of your own transition
surprised you most emotionally?
Denise: My strength. Transition taught me how to overcome hard times. I was the first person to openly transition at
the company where I worked, and I felt a lot of pressure not to mess it up and to make things a little easier for
the people who came after me. Before I transitioned, I thought keeping others at a distance was the emotional price
I would have to pay to transition. I was used to a world where being different wasn’t okay. Instead, I became
friends with some of the people I love most in the world and found a second family. Even the friendships I already
had from wrestling became deeper and more meaningful after I transitioned.
Monika: Many of us feel the pressure to pass as women, and even after surgeries, society keeps judging us. How
do you personally deal with the outside world’s expectations?
Denise: Early on, my goal was basically that if people were going to hassle me, I wanted to be hassled in a good
way. I’m lucky that I blend fairly well, but I also put a lot of effort into figuring out what works for me.
At first, I wore heavy makeup and dressed very feminine all the time. A lot of us don’t get to make those awkward
fashion and makeup mistakes when we’re younger. We’re learning on the fly. It takes time to figure out what works
for your body type and what style feels right for you. Pinterest helps, though.
These days, I don’t really think about it. I know what feels like me. Most days it’s skincare, foundation and
bronzer, cute jeans or sweats, a fitted top and a messy ponytail. Onstage, I hussy it up a bit. Heavier makeup,
slightly tighter jeans, same messy ponytail. Really, it’s about finding what works for you, makes you feel comfortable and then standing by it.
Monika: I remember the time right after my transition, it was pure euphoria. My closet is still full of dresses
and shoes that I literally bought by the dozens back then, and I must have tried on hundreds. I felt like I had
to make up for all those years that were taken from me. Did you feel the same way?
Denise: Yeah, for sure. I shopped a lot. Part of the fun was finally getting to explore all of that, but a lot of
it was also figuring out what worked for me. I think I found my style pretty early on, and it’s evolved over time. I’m still a power shopper, though. I’m terrible with directions everywhere else, but put me in a mall and suddenly
I’m a savant.
|
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“I’m lucky that I blend fairly
well.” |
Monika: How would you describe your personal style? Do you follow any specific fashion trends, or do you have
go-to outfits that make you feel confident?
Denise: Depends on the day. Early on, I used to call my style “edgy skater girl.” I was really inspired by my
friends in the wrestling business. I just loved their style. Then I went through a very Sandra Bullock in The Proposal-inspired “power bitch phase.” After that, I leaned more
ultra feminine and showed a lot more skin. For my special, I leaned into more sexy glam. Like a sexy gazelle in a
mini dress. I like being able to switch it up. Early on, I felt like I was trying to prove something with how I dressed. Now I
don’t really care because I know I clean up okay. These days I’m back to a little edge, a little bling and a much
more casual look, even onstage. Cute jeans, a fitted top and something I can actually move around in usually does
it.
Monika: By the way, do you like being complimented on your looks? Do you find it easy to accept compliments, or
do you struggle with believing them?
Denise: No, I hate compliments. By that I mean please give me as many as possible. Online can be incredibly toxic, so hearing something nice is never a bad thing. Early on, I needed that validation
more because of my own insecurities. I felt the same way about comedy. Now I don’t really need to feel validated,
but hearing someone say something genuinely kind is still A-OK in my book. The backhanded ones are a different story. “I never would have known you were trans” is probably the one I hear
most. I know people mean it as a compliment, but it’s so cringe. One guy asked me, “Are you really a lesbian? I thought you transitioned to date guys.” Then he tried to hit on me.
Monika: Did you ever feel pressure to meet a certain ideal of femininity, like I did by trying to look like the
women around me?
Denise: Early in transition, definitely. I always dressed very feminine and almost always wore heavy makeup. I
felt a lot more pressure to present a certain way. Now I’m much more laid back. I’m better at reading the room, more comfortable in my own skin, and way more secure
than I was when I was younger. I don’t sweat nearly as much of it anymore. I did a workout show last night in sweats and joked that being able to dress like that was one of the best parts
of being a comedian.
Monika: For a lot of trans girls, loneliness can become a part of life. Did you ever feel that, or were you
lucky enough to avoid it?
Denise: Yeah. I think loneliness is common, but not just for trans women. When I transitioned, I moved to Denver and didn’t know anyone. I had given up a lot of relationships and honestly
thought I might not have friends. I cried a lot early on. Some of that was probably too much estrogen. My doctor
looked at my dosage and asked, “Why are you on so much estrogen?” I told her my old doctor had asked if I wanted
more. She said, “Well, we have this thing called science.”
|
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“Being trans isn’t a limitation
or a ceiling on what we can do with our lives.” |
I was lucky to find community pretty quickly through a local gender center, support groups and friends at work.
Later, comedy became another community for me, the same way wrestling had been before. I still get lonely. Dating can be hard, my family lives across the country, and comedy itself can be pretty
isolating. There’s travel, writing, and a lot of time spent working alone. But when I see my comedy friends, it
feels like a family reunion. Zoom, FaceTime and texting make it easier to stay connected too. I’ve realized some of my loneliness probably has less to do with being trans and more to do with the life I chose.
The good thing is there are so many more ways now to find people who share your interests and build a community
around that.
Monika: What do you hope a transgender person watching your special takes away from seeing someone with such an
unconventional path standing confidently in the spotlight?
Denise: Being trans isn’t a limitation or a ceiling on what we can do with our lives. Representation matters
because seeing what’s possible can help us imagine more for ourselves. Embrace what makes you unique. Find what you love. If there’s something you want to do, work hard and go after it.
And if there isn’t a path for you yet, create your own.
Monika: Many trans women are writing their memoirs these days. Have you ever thought about writing your own
book, and if so, what would its central message be?
Denise: Maybe someday. I’ve thought about it. I’ve written a dramatic pilot loosely inspired by my transition,
although I took a lot of situations to their worst-case scenario for the story. I already share so much about my
life on stage that I’m not sure I feel a need to tell my story that way. I really like conversation, so I’d be
more inclined to host a podcast. As for the central message, I think it would be similar to my special: find out
who you are and be you.
Monika: When you imagine the next chapter of Denise Winkelman’s life, what feels more exciting right now, the
possibilities you can already see, or the ones you have not even imagined yet?
Denise: Both. Good things are happening right now, and I’m really excited about where things are going. Stand-up
is the love of my life, and what’s happening right now is everything I could have dreamed of. But I’m also excited
about the things I can’t see yet. So much of my life has taken turns I never could have predicted. I love where I
am, and I’m excited to see what happens next.
END OF PART 2
All photos: courtesy of Denise Winkelman.
© 2026 - Monika Kowalska
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