Monika: There’s this whole “passing” or “non-passing” thing we all face, and even with surgeries, society still judges us. How do you deal with that pressure?
Jenn: I’ve put a lot of work into myself—learning makeup, refining my style, finding the right accessories, maintaining an intense skincare routine, taking a high dose of estradiol, and even undergoing a trachea shave. Some people assume I did all of that just to “pass,” but the truth is, I did it for me.
Yes, I love that I can now walk into public without makeup and not get any extra looks. But every step I took—every change I made—was about becoming the person I always was, even if I didn’t always know it.
The moment I embraced that truth, I stopped caring what others thought of me. If someone has a problem with me, that’s exactly what it is—their problem, not mine. The only opinions that matter to me are from those in my close circles, the people who love and support me for who I am. Society will always judge, but I refuse to live my life by anyone else’s standards. My journey isn’t about “passing”—it’s about being.
Monika: What do you think about the present situation of transgender women in your country?
Jenn: There’s no denying that politics in the United States are polarizing and, at times, downright daunting. But even in the face of it all, I refuse to stop smiling.
Yes, a small but powerful minority is working tirelessly to push us down. But they will never take away my joy. My happiness and power come from within—no policy, no law, no politician can take that from me.
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| "I’ve put a lot of work into myself." |
Monika: I’ve seen some of your photos, and I absolutely love your style - simple, yet so classy and elegant! That’s exactly the kind of look I strive for myself. Where do you get your fashion inspiration from?
Jenn: Thank you so much! My style comes from within—it’s always been something I’ve naturally gravitated toward. I’ve always been drawn to ultra-feminine, classic garments, especially dresses. One of my biggest inspirations is 1950s fashion—I’ve always loved the beautiful fabrics, cinched waists, and full skirts that create such an elegant and timeless silhouette. While I do have a few dresses in that style, my fashion sense has evolved over the years into something that feels uniquely me.
Most of what I wear has a distinctly feminine touch, and as many people have pointed out, my style tends to lean professional. I love polished, put-together looks that exude both confidence and grace.
Probably the most unique thing about my approach to fashion is my process. Whether I was shopping in ‘guy mode’ or as my true self, I’ve always done it the same way: I scan the racks—or scroll online—and wait for a garment to speak to me. If something catches my eye, I pull it out or zoom in, then ask myself, Would this look good on me? If the answer is yes, I check the sizing measurements or hold it up to see if it would fit. And if it passes that test, I try it on—or buy it, try it at home, and return it if it’s not quite right.
For me, fashion isn’t just about clothes—it’s about self-expression. It’s about feeling beautiful, confident, and authentically me in whatever I wear.
Monika: Do you often experiment with your makeup?
Jenn: I experimented with makeup a lot when I was first figuring out who I was. Over the years, I’ve watched countless makeup tutorials, read beauty blogs, and tested out inexpensive products just to practice. But the biggest transformation in my makeup skills came when I invested in a professional lesson at Sephora.
I walked in with a full face of makeup, and the artist immediately gave me valuable feedback—what was working well, what could be improved, and which products might suit me better. She also taught me techniques that I still use to this day.
Another unexpected but amazing learning experience came from my friend’s high school daughter. She offered to teach me more about makeup, and not only did she share some great techniques, but she also introduced me to skincare products that have completely changed my routine. That knowledge made a world of difference, and I’m so grateful to both of them for helping me refine my look.
These days, I don’t experiment as much, but I’ve found a style that makes me feel confident and beautiful—and that’s what matters most to me.
Monika: Do you enjoy the compliments on your looks, or do you ever think, ‘Okay, I get it, I’m fabulous!’?
Jenn: I absolutely appreciate compliments on my looks—it’s always nice to hear kind words about my style or femininity. For so many years, I questioned whether I would ever see the woman I longed to see in the mirror, let alone be validated by others. So now, hearing that recognition is affirming in a way I never take for granted.
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| "I absolutely appreciate compliments on my looks." |
Monika: What was the most surprising part of your transition that you didn’t expect, either positively or negatively?
Jenn: The most surprising part of my transition was how completely it shattered my expectations of what I thought transitioning would be like. Before I transitioned, I was convinced I wanted a long list of surgeries. But as time passed, I kept reassessing and reducing them.
Right now, I’ve had a trachea shave and an orchiectomy, and I’m preparing for bottom surgery. But beyond that? I’ve been so happy with how my breasts have developed and how my face has naturally changed after just two years on HRT that I’m not sure if I’ll pursue facial feminization surgery or breast augmentation at all. That was something I never expected—I thought I would need so much more to feel like myself, but my body has taken me further than I imagined.
I also assumed that transitioning would change everything about me, but in many ways, I’m still the same person. I still love sports, the outdoors, and beer—things I worried wouldn’t “fit” into my identity as a woman. But instead of trying to force myself into an idea of femininity that wasn’t mine, I’ve learned to embrace every part of who I am. And that self-acceptance has actually helped decrease my gender dysphoria in ways I never expected.
Monika: If you could tell your younger self one thing about being a transgender woman, what would it be?
Jenn: I would tell my younger self that while being a transgender woman comes with its challenges—balancing relationships old and new, navigating body changes (especially during that awkward first year), and carrying the weight of those who will hate you—it’s still so worth it.
I’d remind her that transitioning alone doesn’t magically erase gender dysphoria, but finding your Gender Equilibrium™—that balance where your gender identity and your life align—is where true happiness happens. It’s not about checking off a list of surgeries or hitting some external standard of femininity; it’s about becoming comfortable in your own skin and living authentically on your terms.
And most importantly, I’d tell her: You are not broken. You are not a mistake. You are exactly who you were always meant to be.
Monika: Finally, what’s next for Jennifer Marie? What dreams and goals are you working toward now?
Jenn: Right now, I’m working on an exciting new podcast concept—one that goes beyond just gender identity. It’s about gender as a whole and why we are the way we are, but just as importantly, it’s about learning to understand the gender that is opposite of yours. So many of the struggles between men and women—cis or trans—stem from a fundamental lack of understanding. This podcast will explore those dynamics, diving into how gender shapes our experiences, relationships, and interactions with the world. I know this project needs the right team to bring it to life, so I’m taking my time to make sure it’s done right. But when it comes together, I truly believe it will spark real, meaningful conversations that help bridge the gap between misunderstanding and connection.
Beyond that, I’m always working on ways to foster understanding and break down misconceptions. Right now, I’m developing a short course for cis men who want to date trans women. There’s so much misinformation and unnecessary stigma around these relationships, and I want to create a space where men can learn, ask honest questions, and gain the confidence to navigate these relationships with respect and authenticity.
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| "We all deserve to live authentically." |
I’m also planning transformational retreats—and these are so much more than just a meet-up. These will be intensive weekends designed for deep growth, healing, and purpose. They will provide a space where gender-diverse individuals can come together, not just to connect, but to do the real inner work needed to step fully into their authentic selves. Whether it’s navigating identity, overcoming internalized shame, or simply finding the courage to take the next step, these retreats will be about more than just community—they’ll be about transformation.
There’s a lot ahead, but at the heart of it all, my mission remains the same—helping people understand themselves and each other better, and creating spaces where real growth and healing can happen.
Monika: Jenn, this has been such an amazing conversation! Your journey, your work, and your energy are truly inspiring. I’m sure a lot of people reading the interview will feel a little more hopeful and empowered because of you. Thank you so much!
Jenn: Thank you so much, Monika! It’s been such a pleasure sharing my story and having this conversation with you. If even one person feels more hopeful, seen, or empowered after reading this, then I’ve accomplished what I set out to do. We all deserve to live authentically, and my hope is that by sharing my journey, others will feel encouraged to take steps toward their own truth. Thank you again for this wonderful opportunity—I’m truly grateful!
END OF PART 2
You may contact Jennifer Marie on social media:
- Facebook
- BSKY
All photos: courtesy of Jennifer Marie.
© 2025 - Monika Kowalska
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