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?
Bobbie: I remember the recognition more clearly than the exact moment. I grew up in a small town, and there simply weren’t visible transgender people in my everyday world. What I encountered first were fragments, newspaper stories, library books, magazine articles, and what were then called “female impersonators.” That language and framing are dated now, but at the time, it was the only public window into gender variance. I absorbed everything I could find, long before I ever met someone face-to-face.
Monika: So when you finally met women living openly, what shifted for you internally?
Bobbie: The first time I’m confident I spent real time with transgender women in person was in my late twenties, during a business trip to New Orleans. In the French Quarter, I finally had the chance to talk, quietly, one-on-one, with women who were living openly, confidently, and beautifully. What struck me most wasn’t performance or spectacle; it was possibility. These were women who had accessed medical care, who were at ease in their bodies, who moved through the world with a kind of grounded assurance. I remember thinking, Oh. This is real. This isn’t a fantasy or a story, I’m looking at a future that could exist.
Monika: And yet you didn’t act on that recognition right away. What held you, and what stayed with you?
Bobbie: At the time, my own life looked very different. I was married, raising children, deeply invested in trying to perform a version of masculinity that never quite fit. But that encounter planted something lasting. It didn’t push me into immediate action, it gave me permission to imagine myself honestly. I don’t need that kind of mirror anymore. I don’t live my life vicariously. I live it directly. But I remain grateful for that early moment of recognition, because sometimes seeing one person living truthfully is enough to change the trajectory of an entire life.
Monika: I finally felt free after my transition. How about you? Was there a single moment, or maybe a series of moments, where you truly felt like you had stepped into your most authentic self?
Bobbie: For me, freedom didn’t arrive in a single moment, it came in a series of hard, clarifying ones. Coming out ultimately cost me a 35-year marriage. That loss was real, and I don’t minimize it. But there came a point when I understood that not transitioning was costing me my life. I wasn’t failing at marriage, I was disappearing inside it. Choosing to live honestly meant letting go of a future I had once imagined in order to have any future at all. The first real sense of freedom came when I was finally living on my own, fully out, with no secrets left to manage. The people who stayed were the people who truly saw me.
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| With one of her daughters at the ball field watching our son/grandson pitch. |
Monika: And once you were living openly, what surprised you most about the life that emerged?
Bobbie: I had to redefine companionship, and when I did, I discovered something unexpected: I was happier than I had ever been. I wasn’t lying anymore, to anyone, including myself. And then love found me. Being loved completely, without conditions or caveats, was transformative. It showed me what authenticity feels like when it’s mirrored back to you. That sense of wholeness deepened over time, and it culminated in a moment I didn’t anticipate at all.
While preparing for surgery in New York, supported, grounded, and at peace, I realized that the depression I had lived with for decades was simply… gone. Not cured in a dramatic sense, but absent. The symptoms no longer defined my days. With careful guidance, I eventually stopped taking antidepressants, something I never imagined possible. What replaced them wasn’t euphoria, it was alignment. My life finally made sense. So yes, I feel free now, but more than that, I feel integrated. I’m living as myself, without apology or disguise. And that freedom, once found, is not something you ever give back.
Monika: The journey to being our true selves often comes with a heavy price, losing friends, family, and sometimes even our jobs. What was the hardest part of coming out for you, and how did you navigate it?
Bobbie: The hardest part of coming out for me was that it happened without the luxury of careful planning. I didn’t get to map out every contingency around work, housing, relationships, or timing. Once I was out, I had to move forward in real time, inside institutions where I was already deeply known, teaching students and working with colleagues who had known me for years. Professionally, that was terrifying. I was teaching in public schools and at the university level, and there was no option to disappear and reemerge somewhere anonymous. I had to transition in place.
Monika: That “transitioning in place” sounds incredibly intense. How did you emotionally prepare yourself to walk back into those familiar spaces as a newly visible you?
Bobbie: I remember being advised to transfer schools for a fresh start, and then being surprised, deeply surprised, when the leaders around me urged me to stay, promised their support, and meant it. That kind of institutional backing matters. When leadership is clear, it sets the tone for everyone else. Personally, the losses were real. I lost most of my church community overnight. People I thought would always be there simply vanished. That kind of erasure hurts, and it takes time to grieve.
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| "For me, freedom didn’t arrive in a single moment." |
Monika: When so much is shifting at once, work, community, faith, what helped you not shut down or go back into hiding?
Bobbie: What made it possible to keep going was a decision I made with myself. I realized that fear was going to be part of this no matter what, so I chose not to let fear decide for me. I committed fully, mentally, emotionally, and practically, to moving forward. On the first day I returned to work, I made myself a promise: I would hold my head high, look people in the eye, and do my job with confidence and care. And then something remarkable happened. The world didn’t end. My students showed up. My colleagues showed up. My work deepened.
In many ways, I became a better teacher and a more present human being because I was no longer splitting myself in two. The price was real, but so was the return. What carried me through wasn’t bravery in the absence of fear; it was the decision to live honestly anyway, and to trust that integrity would eventually create its own ground to stand on.
Monika: What are your thoughts on the current situation for transgender women in your country?
Bobbie: It’s a difficult moment, and I don’t think anyone who’s paying attention would deny that. The public conversation around transgender women right now is often driven by fear, misinformation, and what I think of as constant rage-bait. If I allowed myself to absorb all of it, all day long, I wouldn’t be effective at anything that actually helps. So I’ve had to be intentional about where I place my attention.
Monika: That balance between staying informed and staying sane is so fragile. How do you decide what to engage with and what to let pass by?
Bobbie: There is real harm happening, particularly at the policy level, and that deserves serious, strategic response. Much of my work right now is focused exactly there: preparing for legislative sessions, coordinating with advocacy organizations, identifying allies, and doing the unglamorous, necessary work of persuasion and protection. That work requires steadiness, not constant outrage.
Monika: You mention steadiness. In such a hostile climate, where do you personally draw strength from to keep doing this kind of work?
Bobbie: At the same time, I’ve learned that communities don’t survive on resistance alone. They survive on meaning, connection, and hope. That’s why I also invest my energy in spaces that help people strengthen their inner lives, because people who are grounded, resilient, and connected are much harder to erase.
My work with Trans Gurus, for example, is intentionally non-political. We talk about spiritual growth, courage, character, creativity, and moving out of fear and bitterness into joy and purpose. That kind of inner work matters, especially in hostile climates. So my view of the current situation is this: it’s serious, it’s challenging, and it demands thoughtful action. But I refuse to let constant alarm define my days. I choose to focus on the work that actually changes lives, one conversation, one institution, one community at a time. That’s how I stay hopeful, and that’s how I stay useful. And for anyone interested, our Trans Gurus YouTube channel on January 1, 2026 had over 126K subscribers and over 650K views.
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?
Bobbie: This is a question I answer very carefully, because there is no single right way to be a woman, and certainly no universal obligation to “pass.” I want to be clear from the start that what I’m describing is my personal reality, not a standard I believe others should meet. I’m very aware that passing privilege exists, and I’m also aware that not everyone has access to it, or even wants it. Many trans and nonbinary people live full, courageous lives without centering passing at all, and I respect that deeply.
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| With Kathy Baldock, a world-renown biblical scholar. |
Bobbie: For me, though, the context matters. I live and work primarily in the Deep South. I travel frequently through states and communities where hostility toward transgender people is very real. In that environment, being read as a woman is not about validation or perfection, it’s about safety, access, and being able to move through the world without constant interruption or threat. I want to use a public restroom, board a plane, sit in a restaurant, and do my work without becoming a flashpoint.
Monika: When you’re in those spaces, airports, restrooms, classrooms, what are some of the small, practical things you pay attention to that help you feel more at ease?
Bobbie: So I treat my transition as an ongoing learning process. I pay attention to how I move, how I speak, how I carry myself, not as a judgment, but as information. I don’t think of missteps as failures; I think of them as feedback. Over time, that attention has helped me feel more at ease in my body and more secure in public spaces. I also recognize that I benefit from forms of privilege I didn’t earn, race, education, resources, and access to care. I don’t take that lightly. It makes me more careful, not less, about how I speak on this topic. Ultimately, the way I navigate the outside world is about alignment. I do what allows me to live safely, effectively, and authentically in my own circumstances. And I hold space for others to do exactly the same, in whatever way makes sense for their lives.
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?
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?
Bobbie: Oh yes, I completely recognize that phase. There’s something wonderfully liberating about finally having your own space and realizing you only need one wardrobe now, the one that actually belongs to you. After years of dressing for someone else’s expectations, suddenly being able to choose freely feels like opening the floodgates. Dresses, shoes, makeup, colors you never let yourself touch, it’s joyful, and it’s playful, and honestly, it’s part of catching up with yourself. I definitely went through that burst of enthusiasm. Trying things on, experimenting, making plenty of questionable choices along the way, it’s all part of the learning curve.
Monika: At some point the rush slows down. Was there a moment when you noticed your relationship to clothes and appearance shifting from “making up for lost time” to something calmer?
Bobbie: I’ve always said transition is a grand adventure in trial-and-error learning, and nowhere is that more true than in closets and makeup drawers. What I discovered over time, though, is that joy eventually wants a little discernment. Clutter can start to weigh on you energetically, and not everything you buy in that early excitement ends up being something you truly love or wear. So the abundance slowly gives way to intention, figuring out what actually feels like you, what you reach for again and again. But I wouldn’t trade that early phase for anything. It’s a celebration. It’s permission. And it’s a very human way of saying, I finally get to be here.
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?
Bobbie: I think of my personal style as intentional rather than trendy. At this stage of my life, I’m an older woman, a professional, and someone who spends a lot of time in public, on camera, on panels, and in advocacy spaces. So my style has to do a few things at once: it needs to feel authentic, polished, and approachable. Over time, I’ve learned to keep it simple. I really only have two rules, and they’ve served me well. First, it has to fit. Second, I have to genuinely love the way I look in it. If both of those are true, I don’t worry much about trends or even price.
Monika: That sounds wonderfully grounded. When you’re choosing what to wear for a talk or a recording, what are you paying attention to beyond just the mirror, maybe the message your clothes are sending?
Bobbie: What I’ve noticed is that people end up with closets full of clothes they don’t wear because they bought things for the wrong reasons, because they were on sale, or because they seemed like a good idea at the time, not because they actually felt right. I’ve also learned what works for my body and coloring. I’m not petite, and I don’t pretend to be. I tend to gravitate toward solid colors rather than busy patterns, and I choose pieces that work with my hair and eye color rather than fighting them. When something fits well and feels aligned, it shows, both in how I carry myself and in how comfortable I feel in the world. So my go-to outfits aren’t about fashion statements. They’re about feeling confident, grounded, and fully present. When my clothes support that, I know I’ve chosen well.
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?
Bobbie: I do struggle with compliments, honestly. I know the right response is simply to say “thank you,” and I’ve learned not to deflect or explain them away, but that doesn’t mean they come easily. For a long time before transition, I wasn’t comfortable seeing myself at all. I avoided mirrors, and I really disliked having my picture taken.
When I look back at family photo albums, there are hundreds of pictures of everyone else and very few of me, and that wasn’t accidental. Living in a body that didn’t feel like home made it hard to accept being seen, let alone praised. So when someone offers a compliment now, it still catches me a little off guard. I don’t dismiss them, but I do receive them slowly. I think of them less as something I have to believe immediately and more as gentle feedback, small confirmations that I’m moving in the right direction, that I’m more at ease in my skin than I once was. I’m learning to let compliments land without arguing with them. That, in itself, feels like a quiet kind of progress.
END OF PART 2
All photos: courtesy of Bobbie Dodds Glass.
© 2026 - Monika Kowalska
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