Monika: Let’s introduce Fantasia Fair to those who may not be familiar with it. Fantasia Fair (also known as FanFair) is a week-long conference held every October in Provincetown, Massachusetts. Established in 1975, it is the longest-running transgender conference in the U.S., providing a safe space for attendees to explore their gender identities, connect with peers, and advocate for their rights. Now known as TransWeek, it celebrated its 50th anniversary in October 2024. Back in the pre-Internet days, that was the place to make connections, right?
Vanessa: Actually, TransWeek (formerly Fantasia Fair) is the longest continuously running trans event on the planet! And no, this did not start as a place for us to “advocate for our rights”, at least not in 1983. It was designed as a fun event, something enjoyable, not political!
My first time at Fantasia Fair, I met our trans pioneer Merissa Sherrill Lynn, founder of the legendary Tiffany Club support group. Lost in the “pink fog” (that unrealistic euphoric sense when being ‘out’ for the first time), I suggested to her that we should go public, let the world know we’re not monsters or freaks, and even lobby Congress for beneficial laws. To my surprise, Merissa raised her voice and cut me off at the knees: “No, we should not do that, it’s a mistake. And if you do something like this, I will oppose you every step of the way! Outing us to the world will give them a reason to come after us!”
Monika: That must have been tough to hear at the time, especially with your enthusiasm for making a difference.
Vanessa: Yes, that hurt my feelings. But in her defense, it was almost a premonition of what we’re facing now in the U.S., trans people are firmly on their radar, and they are doing everything possible to negatively impact us. As Project 2025 outlined, their goal is that we “no longer exist.” Forty years later, I see her point. For the record, Lynn did eventually soften her stance on trans advocacy and became a supporter in spirit in later years.
As you noted, Fantasia Fair was created to provide a safe space, a way to connect with other trans people (and helping professionals) while also offering practical information, like voice training (which I took my first time with Linda Wheeler). It gave us confidence and a roadmap for our journeys. Other than the pandemic shutdown, TransWeek/Fantasia Fair has taken place every year in the same town: Provincetown, MA.
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| "Going to my 35th reunion in 2010 was a blast" |
Monika: I’ve heard Provincetown described as a one-of-a-kind place. Is it truly as special as people say?
Vanessa: The town itself makes the event. Not only is it a unique New England beach resort, but it has long been a gay mecca for the LGBTQ+ community. Unlike other hotel-anchored conferences that keep you in a cocoon, this event forced you to traverse the streets and interact in public, with little to no fear of backlash.
That said, my first time being accosted did happen there in ‘83. A quasi-drunk townie struck up what started as an amicable conversation but suddenly flipped, shoving me hard into the pharmacy wall and threatening more, had I not stood up and given him the indication I would fight back. Over the years, though, the town’s police force became much more vigilant in protecting attendees. They even made presentations to us, stating that they take any incidents very seriously and will not hesitate to arrest, bring charges, and push for hate crime enhancements. Today, it’s extremely safe.
Monika: How did you first hear about Fantasia Fair?
Vanessa: As for me personally, learning about Fantasia Fair, or anything trans, was impossible until 1980. That year, I had a Playboy subscription (and, geek that I was, read it cover to cover like a book). That’s how I came across an article by D. Keith Mano about Fantasia Fair! It was a watershed moment.
Before that, I had only learned what “transsexual” meant in 1976 when Renée Richards came out. The Playboy article introduced me to the concept of "heterosexual crossdressers", something I’d never heard of before. It was an epiphany, as my prior hetero tendencies had me repressing myself. Like most people in South Texas, I had mistakenly believed that if you were a “transvestite” or a drag queen, you had to be gay.
The only time I attempted to buy clothes and visit the one gay bar in town, they laughed at me and refused to let me in, saying I was “in drag” and violating their dress code! I threw everything away the next morning, convinced I was a failure at being gay before I even had a chance to figure it out.
At least that Playboy article educated me. It introduced me to terms like “transgender” and informed me about actual trans social support clubs and bars (though all were in the Northeast, Chicago, or the West Coast). Most importantly, it gave me the name Fantasia Fair, along with its contact information!
Monika: Was there an admission fee for attending, or was it free to participate?
Vanessa: It took me three years to save up for the event fee and to purchase clothes and makeup (mostly from catalogs I learned about in the article or at a K-Mart across the bay from Corpus Christi). Fun fact: It was those very K-Mart purchases that Mariette Pathy Allen photographed me in for her first book, Transformations.
In 1983, I drove cross-country in my old Ford Maverick, every stitch of femme clothing piled in the back seat! While I wasn’t polished in my presentation (I looked like a street girl straight out of New York), I made it work on my first time out. And it was thanks to Ariadne Kane coaxing me up there, and being at Fantasia Fair, that I learned all the basics to get started.
Even better, I made a friend in Mariette, who connected me to others and has stayed in my life all these years. That was a godsend.
Monika: Transitioning is not just a personal journey; it also reshapes our relationships, especially with those who support us. Have you noticed a shift in how people treat you since your transition?
Vanessa: That was almost three decades ago, but yes, I did. Overall, it turned out mostly positive! My dad, in his own way, was more okay with it than I expected (even though he always deadnamed me or misgendered me, I went easy on him, though). Surprisingly, my mom took it the hardest, despite having a gay best friend. Her reasoning was, “Why can’t you just be gay?” She and my sisters struggled with it at first, but they all came around in time. Most of my friends were initially surprised but had no real issues with it, though there were a couple of exceptions.
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| Playboy (1980 November) |
Monika: Oh yes, school reunions are definitely something special! When I attended mine, our name tags had our senior class pictures on them, so I instantly became the center of attention, people kept asking if my tag was really mine!
How did you end up in the spotlight at yours? For me, it was quite a shift. I hardly had any friends in school, but at the reunion, all the ladies suddenly wanted to chat, and some of the guys were eager to dance with me and buy me drinks. Quite the change!
Vanessa: LOL! Ironically, at our 20th reunion, a classmate from elementary school (Sharon Perry) and a football player (Richard Guerra) decided to pull a prank and switch nametags, it was a hit! A few months after that came my own first HRT and transition, so maybe it gave me ideas.
We didn’t have a 30th reunion (which I was looking forward to) because nobody stepped up to organize it. But for our 35th, I got a notice from our current organizer, Lorrie (who was in my 6th-grade class), and an old friend, Joey, about the reunion. When I responded to their emails, they never made the connection as to who I was!
At the 35th reunion itself, we didn’t have senior year badges at our initial get-together, so Joey, Lorrie, and others still had no clue who I was until I told them face-to-face—and also informed them that my fiancé at the time was female-to-male! Everyone there got an in-person lesson in Trans 101.
The reason I was “in the spotlight” was that I told Joey (who was going to DJ) that I had thousands of LPs recorded and categorized as MP3s on my computer, including most of the music from our high school era. So, he tabbed me as the DJ instead. And yes, I was right there onstage (albeit not speaking) for all to see! The support was overwhelmingly near-unanimous.
Monika: Did you attend any more reunions after that?
Vanessa: Four years ago, I attended our 45th (pandemic-delayed) reunion, still no issues at all, though it was a much smaller crowd. This year, I’m helping the committee by sending Joey my high school-era music, helping attract advertisers for our booklet, handling decorations at Moravian Hall, etc. But attending is vexing me.
I want this to be a successful and wonderful experience for everyone, especially since many more are coming this time, but I don’t want to be a distraction or disruption. This is the worst possible year for a trans woman like me to attend a reunion in conservative South Texas, thanks to Trump! Murphy’s Law strikes again!
It doesn’t help that I’ve had intense back-and-forths with a few classmates online (a couple even defriended me), and those tensions never fully disappeared. Some of my friends on the committee are trying to entice me, some even begging, promising, “Nothing will happen, they’ll have to come through me!” It’s touching, but it’s also no guarantee of safety.
So, whether I go remains to be determined.
Monika: Returning to your family dynamics, it’s understandable that your parents struggled with it, but why did your sisters have such a negative response? I was fortunate to have a very supportive sister, so I’m curious, what made things different in your case?
Vanessa: My family structure: I was the oldest, the protector for my sisters and my little brother, so they looked up to me. As my siblings went through their issues, where my mom would have to bail them out or take them in, I was always the “rock” my mom (and even my dad) depended on, whether for borrowing money or acting as a stand-in guardian of sorts. They all apparently thought I would never have any issues or problems like the rest of the family. My coming out threw their worlds for a loop, and for that reason, particularly for my sisters, they took it hard. Both my sisters, at various times, tearfully told me I was “killing off their big brother.” Even though I reassured them that my personality hadn’t changed, their first impressions and fears weren’t hard for me to understand.
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| "Google started as a great tool, but it became the bane of my life after that." |
Monika: We all know the journey to being our true selves comes with a heavy price. Like, losing friends, family, jobs, and all that. I must say I am one of them. Did you have to pay a heavy price for being you? What was the toughest part of your coming out?
Vanessa: The super-fast body changes took me completely by surprise, and I didn’t understand them until I got my karyotype results a year and a half ago. That’s when I realized I had a chromosomal abnormality. The poverty was another challenge, not just right after transitioning, but intermittently afterward beginning in 2003. Employers started using Google the same way I was using it, something I discovered during a job interview in early 2004. About the dumbest thing I ever did was not check to see if Google, but employers sure did! With all the people, legislators, bills, and other research subjects I’d looked up, you’d think I would have wondered about that sooner, but I was too busy searching everything else!
Google started as a great tool, but it became the bane of my life after that. Employers didn’t just find my name, they found my politics, activism, protests, press releases, and quotes from groups like NTAC, TGAIN, and the Women’s Political Caucus (one of which even pissed off Tom DeLay). They could also see photos of me out in the streets, waving signs, and participating in Occupy. Employers were already hesitant about considering Trans women, but throw in thousands of Google hits showing my liberal, firebrand ways, and even my involvement in organizing these events. So the more conservative, buttoned-down bosses became very skittish about having someone like me in their workplace. While I try to keep my work and extracurricular activities separate and behave differently in the office, they wouldn’t know that. The toughest part was definitely the economic side of transition.
Monika: How do you handle the pressure of "passing," given the constant judgment society places on our appearance?
Vanessa: This was the least of my worries. Pretty early on, I had the ability to pass, and I considered myself blessed for it. It didn’t help me keep my job, but at least I could ‘pull it off’ with prospective employers when I had to notify them that my legal name was still male at the end of the interview. That was often a deal-breaker. That said, I had the passing privilege that ‘true transsexuals’ have, as Denise Norris put it. Unlike them, however, I didn’t have the ideal transition or a stealth life, which, in hindsight, has been a blessing in disguise. Had I done what I initially set out to do, I would have become one of those 'I’ve got mine, it doesn’t affect me' transsexuals, wrapped up in my own life with little to no concern for the rest of our community. Yes, I’d have had a husband, a ‘normie’ life, a career, and likely a life with much less stress and more financial security then and now. But, Murphy’s Law!
Monika: That must have been a challenging reality to navigate.
Vanessa: This forced me to do the opposite of all my passable peers, to genuinely care about the community situation (including my friends who had it worse), and to use my passing privilege to get into spaces with other communities, meet them, get to know them (and them, me), and then casually drop a notion like, ‘I know about Trans stuff. I am Trans.’ By then, it was too late! I was already in their space, whether it was lesbian-only, conservative Republicans, or machismo guy-land. They already liked me, so it made it hard for them to do a hard 180 without looking paranoid and stupid. And it gave me the opportunity to advocate in spaces they wouldn’t let us into if they ‘saw us coming.’ It was something that could impact those who didn’t have my blessings, particularly people like Karen Peppard and Stephanie Rhynes, who didn’t quite make it to an easy life. In my view, it became my responsibility to do something with it.
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| "Pretty early on, I had the ability to pass, and I considered myself blessed for it." |
Vanessa: In the U.S., whether for Trans women or Trans men, the situation right now is harrowing. In the past couple of years, since the COVID pandemic passed, we’ve witnessed a sociopolitical paradigm shift in the country. With this new cultural movement, the goal seems to be to vilify the pre-COVID world and replace it with a new, moralistic, and chauvinistic vision for the ‘New America,’ as they see it. To achieve this, they’re pitting wealth against ‘leeches’ (the non-wealthy), male against feminism (anti-women), conservative religion against globalist humanism (mainstream Protestants and atheists alike), white nationalism against the ‘immigrant invasion’ (including legal immigrants and people with darker skin), and traditional family values against ‘amoralism’ (which includes divorced people, the GLB community, and especially Trans individuals).
Monika: And we end up falling prey to this rhetoric.
Vanessa: Trans people are seen as one of the first victories they want to score, using us as a stepping stone to gain momentum for further victories. As the first target, Trans people are largely fighting this battle alone, with other communities fearful that they could be next in the crosshairs of this movement.
Over the decades, Trans people have made significant social and political gains, only to see most of them almost evaporate in less than a month. There are very few political safe havens left, even Democrats are running from us. We’ve had some initial delays thanks to the judiciary, but the long-term question is: 'How long will that hold?'
We’re on the brink of a drastic shift that could have a major impact on the Trans community in the U.S. My greatest hope is that our community can find a way to stay safe and survive, whether in this country or elsewhere. My fear is that Trump and Musk have many more dirty tricks up their sleeves, and we’ve only seen the tip of the spear. Right now, I’m struggling to find any optimism.
Monika: What really boggles my mind is why we were singled out for attack, why us, out of all the groups in the LGBT community? Is it because we’re seen as the weakest and least numerous?
Vanessa: That’s exactly why. In truth, we are one of the smallest, most vulnerable, and income-insecure communities, with the fewest advocates willing to stand up for us in these situations. It’s tactically strategic, as I mentioned earlier. Due to our size and socioeconomic position, we’re an easy victory, a catalyst to propel them further afterward. It’s not a carbon copy, but there’s historical (and tactical) precedent from a bit over 90 years ago. Then, as now, trans and drag folks were among the very first they eliminated before moving up the iteration to other groups in their social and moral cleansing movement. For me, their targeting us first was unsurprising.
Monika: What was the most surprising part of your transition that you didn’t expect, either positively or negatively?
Vanessa: The most surprising part, I guess, was finding out a year and a half ago that I had a chromosomal deletion (about half of my Y chromosome), which explained why I had such a strange puberty in junior high. It also likely explains my lightning-fast body transformation, though it didn’t take away the body hair the way I was told it would! Coarse, dark brown hair on B cup breasts is not a good look! My TATS friends used to tell me, ‘You’re a natural!’ They mostly said it to calm me down and ease my insecurities, but in retrospect, they might have been right.
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| "I also wish I had found the personal relationship." |
Vanessa: No. Or at least, I didn’t consider it at all until my friend Ethan St. Pierre and I discussed the Trans community’s history, how HRC was trying to take ownership of or whitewash our community’s history politically, and their problematic relationship with us over the years. That conversation did make me pause and consider it, especially since we were both there for these events and can speak to them firsthand. Even with that, my biggest concern is that writing a book about myself feels like an exercise in egotism.
Yes, I’ve had people like Ethan, Lisa Gilinger, and others encourage me, surprisingly, even a Trump-voting MAGA couple from Illinois I met a few weeks ago. I educated them over a few days about Trans issues and shared my story. To have him, of all people, tell me to write a book about my ‘interesting experiences’ because ‘it might help someone someday’ was Twilight Zone-bizarre! In my mind, everyone has interesting experiences, so why would mine be worth turning into a book? And if ego is the enemy, why feed it? So mostly, no. But I’ll reconsider Ethan’s points at a later time, there’s just too much going on right now.
Monika: If you could tell your younger self one thing about being a transgender woman, what would it be?
Vanessa: Obviously, I wish I could have transitioned earlier, instead of waiting until I was 38. And I wish I had known the personal cost of political activism, so I could have warned myself to call it quits much sooner. Dallas Denny once said the typical shelf-life of a Trans activist was four years, I ended up going through three times that length before I finally realized it was for nothing. I also wish I had found the personal relationship I had always hoped for much sooner; it would have saved a lot of empty wistfulness. But you never know until you know, so…
Monika: Finally, what’s next for Vanessa? What dreams and goals are you working toward now?
Vanessa: Expatriating out of the country for my retirement! And with any luck, I’ll find the “man of my dreams” … someone I can settle down with, and finally figuring out if love exists(?) Maybe get married and see what that’s like. Who knows? Mostly just to have a stress-free and happy life! That would be nice!
Monika: Well, it sounds like we’re both on the same quest, searching for that elusive ‘man of our dreams.’ Here’s hoping he’s out there, and maybe we’ll both stumble upon him soon. Best of luck with your search, Vanessa. I’m sure he’s just around the corner... let’s just hope he knows how to find you!
Vanessa: iPos claro! And thank you for the opportunity! Hopefully my long-winded responses didn’t bore everyone to sleep, LOL!
END OF PART 3
All photos: courtesy of Vanessa Edwards Foster, unless otherwise noted.
© 2025 - Monika Kowalska
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