My Experiences as a Transgender Woman Using Dating Apps
Welcome to Love Transcends, a special project by Cosmopolitan that celebrates the resilience, wisdom, hope, and joy of the trans community as its members navigate romantic love. Through in-depth interviews and personal essays, trans people share what it's like to date, hook up, break up, and fall in and hold onto love in the midst of sweeping anti-trans legislation and attacks on personal safeties and freedoms of expression. Click here to see the entire collection.
I have always been a member of the LGBTQIA+ community, but about six years ago, I made the shift from 'G' to 'T.' Before transitioning, dating men was the one part of my gender and sexuality that made total sense. I loved being gay. For me, being a man who was dating other men was a way to bond with my partners; there's a closeness between lovers that comes from having a similar experience in the world.
After I transitioned, it was hard to let go of that part of my identity. I tried dating other trans women but couldn't make it work. And so, aside from the occasional sapphic make-out, I had to grudgingly accept that I am a straight woman—and that, while heteronormativity is everywhere, I didn't know the rules. Putting myself out there meant learning new references and dynamics.
I took a deep breath and dove into the internet—the place we all go to be collectively, unwillingly traumatized. Ask any trans woman who's been online about how we are hypersexualized by men, especially on dating apps. At first, I imagined these intensely sexual communications would lead to actual relationships. In reality, though, it was just all a fire hose of lasciviousness, with the men I met falling into a few distinct categories.
A blank profile pinged me on Grindr. When I responded, the guy sent over a photo of himself, a rugged and handsome man next to a motorcycle. I recognized his face. 'Mike,' as he called himself, was an actor who had played a mythical being in a show I'd watched. There'd been full frontal nudity and let's just say the image had stuck with me. I felt like a powerful sex witch who'd tranifested (a transgender woman doesn't manifest, she tranifests, thank you very much) this gorgeous man.
He told me he worked in 'the industry' and in Los Angeles, where I live, everyone knows that means Hollywood. I played it cool—L.A. is full of TV people. He was looking for hookups but ones that could hold his attention. Honestly, it felt like a bad fit, but I took the bait and told him I was 'killing time' on Grindr.
'I hope I survive the slaughtering,' he replied.
'The time won't, for sure,' I texted back. 'It will have its revenge one day, but hopefully not today,' I added, with the fingers crossed emoji.
Mike told me that sounded like a line from a J.R.R. Tolkien novel. 'You might be a writer and not know it,' he said. I clocked the patronizing tone but sweetly texted back, 'Lol, I am a writer.'
We agreed to connect offline and for a few weeks, I'd meet Mike at a coffee shop, a cute East L.A. corner store, and my apartment—but never for more than 15 minutes or so. At first, I was excited that he was making time for me, but I quickly realized he didn't want to be seen in public together and possibly 'outed' as someone who is 'trans-attracted.'
I was jolted by the realization that there's nothing for a man in Hollywood to gain by dating a trans girl. I never told him I knew who he was—I didn't want to seem weirdly parasocial. I thought he'd tell me at some point. Instead, he lied about his last name when I asked him.
Another app match, and it was clear from the moment I walked into the wine bar for our first date that no one loves a poly musician more than a poly musician. I pulled up a stool next to him and he told me he'd forgotten his wallet. The bar didn't take Apple Pay and he wanted me to cover the bill. He'd Venmo me later, he promised. This seems stupid but sure, I thought, and ordered myself an orange wine.
I told him I don't hook up on first dates and proceeded to watch him love bomb me over the course of the evening. Since I was already in fuck it mode, I decided to bring him home. Horny, chaotic sex ensued. My apartment at the time had a huge balcony overlooking Echo Park, and the next morning, we chatted about how fun it would be for him to fuck me there, looking down on the world. Then we went for coffee with my giant sweet dog at a shop where some of my friends worked as baristas. They did accept Apple Pay, so he got us coffee, we chatted with my friends, and then parted ways.
Except he went back to that same shop the next day to tell one of my barista friends, 'You just have this light in you.' Every woman knows that is creep for 'I want to suck your life force.' When I learned he refused to leave until she gave him her Instagram, I sent him a voice memo saying, 'Thank you for the good time. It was really fun, but I heard what happened at the coffee shop and that's really chaotic. I don't want to get involved.'
At least I was learning.
By the time I met my first Malibu Daddy, I understood the constant anxiety that chasers (people who fetishize trans women and don't treat us like whole people) always carry. No matter that it's the 2020s, I read as a woman in any room I enter, and he was rich enough to do whatever he wanted. I could tell that, for both of us, fear held on tight.
Still, this was a chaser with style and money and we had real chemistry. We hooked up at his gorgeous house the night I saw the new Hellraiser. I was inspired, so we played the original Hellraiser in the background and he begged for my cum in his mouth. It was sweet, though, and he held me close after. He said we had a 'good connection' and drove me home in his Maserati.
My earlier naivete was gone. I knew by then not to invest. High-profile men may seem interested in you, but they give you almost nothing and act like it's special treatment. Most beautiful women, cis or trans, experience this: The dating is transactional. The men flex their status and can be weirdly uptight about money. Once, when I was sick, I asked this Malibu Daddy to send me sushi. He did and kept reminding me how expensive it was, warning me not to waste it.
In my early days as a trans woman on the apps and in the world, it was thrilling and validating when men treated me like a delicate flower or catcalled me on the street. Passing as myself was exciting, but this kind of trans-affirming misogyny was like whiplash. The privilege of assimilation only came at a distance.
If my voice were a little too deep one day or a man got a little too close or if I fought back or argued when he said something condescending or misogynistic, would he kill me? I think this is something every trans—and cis—woman has experienced to some degree. Actual love seems rare in this world. It makes me sad to think of these men missing out on deeper, sexier connections. Dating them felt like squeezing a stone and hoping for blood.
This is why, last fall, I decided to take a complete break from the apps until the end of the year. I couldn't shake the feeling that I had missed some basic experiences of being treated with dignity by other people. One half of me shrugged it off thinking, That's love and that's life, get over it. Another part of me stopped, looked around, and thought, Is this really the world we wake up to and recreate every day?
I clearly needed space. If I were going to establish a connection, it would have to start in my real life and be part of my existence in my community.
That didn't happen, but in March, I had a dream that I was getting a piggyback ride from a handsome man in a field covered in wildflowers. My 'boyfriend' in the dream watched us looking sad. My hand was resting on the handsome man's chest. I let it get heavier, and he moaned. I pulled back a lock of his hair, leaned into his ear, and exhaled gently.
'I haven't seen this side of you in such a long time,' he said.
'I know,' I replied. He held my gaze and said, 'It's so nice.'
I woke up nodding in response. I felt at peace, like something had shifted. A few days later, I decided to download Hinge. I'd been on it before and liked that the people there are allegedly looking for relationships. Unlike Grindr or Taimi, it sets daily limits on how many people you can Like. I didn't want to get sucked into checking my phone for dead-end responses all day and night.
To my pleasant surprise, I matched with a finsexual guy—meaning someone who's attracted to feminine people, regardless of whether they're cis or trans. He was so excited about me, he wanted to meet up the same weekend.
He was from a conservative part of L.A. and someone I wouldn't have considered before, but I gave him a chance. On our date, he was thoughtful, caring, and nice. He was openly interested in me and a lot taller than I am (win, I'm 5'11"). He even screenshotted my list of must-avoid foods so he'd remember what I can't eat when we went out to lunch. During our conversation, I mentioned that one of my trans mothers says, 'A man will take you out in public, but will he take you home to meet his family?' He responded that he'd had the 'trans talk' with his mother five years ago.
It was wholesome. He even has similar piercing blue eyes as the man in my dream did. I don't know what will come of our time together, but I can tell that my sense of dignity is growing. For the first time, I feel like I can move toward the right match, lay my hand on his chest, look him in his eyes and say, 'It's so nice.'
For an expanded list of resources specific to the trans community, click here.
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