My bio on Grindr read: “Be trans friendly. Send face to chat.”
It was difficult to be on a gay hookup app as a trans woman. Most men in my feed desired to only sleep with each other. But I knew there were straight men on Grindr who hungered for a woman like me. I wanted them too.
That’s where I met Jack. At 22, he was a few months older than me, and, other than his age, his entire profile was blank, usually an indicator of a cisgender straight man who was guarded about his attraction to trans women. Typically, the messages I received would start with a vulgar sext, sometimes an unwanted nude photo.
Living in Morningside Heights, I was attending Fordham University for my master’s degree in strategic communication. One night I was up late working when I received a Grindr message from him, a selfie. Amid his light brown hair, two-day scruff and meek gaze, his lacrosse T-shirt stood out to me the most. He looked like a sporty boy I would have crushed on in high school.
He followed up his photo with “Hello.”
Messages in my Grindr inbox tended to cut to the chase: “Down for now?” “Car sesh?” Men who contacted me because they fantasized about trans women made it difficult for me to feel seen as a person in general, let alone a person worthy of respect.
Although my interest was piqued by Jack’s picture, it was his gentleness that drew me in.
Our sporadic small talk was harmless, spanning two months. I brushed him off, but as I commuted to school and spent hours in the library, he was persistent.
“My sex drive is pretty low these days,” I wrote. “Give me a bit and I’ll hit you up.”
“OK.”
When I turned back to my studies, he added, “Just so you know, we can do non-sex things and hang out too. It would be fun.”
This became our pattern: he being distant enough to show interest without pressure, and me appreciating his laxity, given my demanding schoolwork. His ease led me to trust him, so we set up a day to meet.
The first afternoon Jack came over, he admired my bathtub and drank his cup of water with two hands. His poised demeanor in a beige wool peacoat and long scarf reminded me, in a good way, of John Bender in “The Breakfast Club.” In my bedroom, he fixated on my yellow Power Ranger figurines, noticing my framed academic award next to them on the windowsill.
“You went to SUNY Oneonta?” he said. “I went to SUNY Potsdam.”
I pictured my friends who also attended Potsdam eating in the same cafeteria as Jack, getting drunk at the same frat party. Suddenly, the person I’d seen as a stranger now fit into my world.
I imagined what the deer looked like from his dorm room window, roaming the grass at dawn. Or how he spent his day when the school canceled classes because of snow. Or where he would have gone if his parents were able to afford private school.
We sat on my bed, my back leaning against the wall. He slouched his head onto my hip and wrapped his arms around my waist. “This is weird,” I thought. Aside from sexual intimacy, my hookups were typically aromantic, absent of cuddling and expressions of affection.
I kissed him and rolled on top. I took off my shirt and he hugged me tight. His face dug into my chest as he said, “I like you. I think you’re really cool.”
Unsure how I actually felt, I said, “Oh. I think you’re really cool, too.”
The next time I saw Jack, he spent the night at my place. It was then, awake in bed at 4 a.m., that I realized I had never let a guy sleep over before. His heat warmed the bed, so I crept to the bathroom to cool off. I Snapchatted a disoriented selfie to my friends, my hair messy and eyes bloodshot.
“How do you guys do this sleepover thing?” I wrote. “I can’t sleep at all.”
Customarily, my flings with strange men were brief. The men did not take note of my bathtub or my educational history before sex, and they did not linger after.
I came back into bed, disturbed by the rumble of his snoring, but his sleeping face on my pillow struck me. For the first time, the thought of sharing a bed with a man did not come from pure imagination. I now had a real image for this fantasy; I could pretend Jack was my boyfriend, reach for his face and whisper “I love you, good night,” then fall asleep and meet him somewhere in his dream as if we had done this a hundred times before.
The next day, he flew off to see his family for the holidays and the first weeks of the new year.
“merry crimmus,” I texted.
“u too, babygirl,” he replied.
After our sleepover, I didn’t hear from him unless I initiated — an unexpected change. Instead of giving in to my insecurity that the sleepover meant little to him, and therefore I meant little, I imagined other scenarios: him asking me to sleep at his place, for a change, or spontaneously calling me while I’m in line for my morning coffee. But because I had presumed a sex-only expectation from the start, I shamed myself for developing feelings.
“miss u,” he texted one random morning.
“really?”
We stayed in touch and occasionally saw each other, weeks in between. On a hot morning, he snored behind me as I sat on the floor beside my bed, working on my final thesis. He put his hand up to my face, letting me know he was awake. With my eyes on the laptop screen, I took his hand and planted kisses in his palm, wallowing in these ordinary joys — the kind of affection I slowly grew comfortable displaying.
Longing to be more than casual with him, I sought a therapist to guide me through my growing feelings.
Jack’s periodic “miss u” texts progressed with heart emojis, an unprecedented closeness. And I returned the sentiment. It felt thrilling to express my adoration so directly, until the weeks between seeing each other and texting ultimately turned into months of silence I knew to be ghosting.
I relied on Grindr as my safe dock because dating as trans is complicated. Sleeping around was easier for me. I had set the bar low, then met Jack, who saw me as more than a fantasized body, only to have his mysterious exit echo a looming insecurity I avoided for years: Being trans implies I am not real enough to deserve decency.
I broke down in therapy, mustering the courage to say out loud what was undeniably true: “He left me.”
“I don’t mean to put this on you,” my therapist said, “but could him being a cis straight man and you being a trans woman play a part?”
I didn’t want to blame Jack, who showed me a new realm of affection that made desire feel as simple as just a boy and a girl who liked each other. But he made leaving simple, too; all of this could still not be enough.
Deep down, I denied how my mere existence as a trans woman could ever cost him. Jack, in wooing me, nurtured the possibility that my romantic fantasies could come true, that I could be seen as a complex person rather than a fetishized token of someone’s imagination. After being deserted by him, I ruminated on my insecurity that being trans denied me of even a simple goodbye.
And yet I know myself to be real because my transition, as a teenager, required exceptional certainty. Doctors and psychiatrists double-checked my decision constantly.
“Yes, I’m sure,” I repeated, and I became more real each year. With Jack, I felt even realer. Not only had he seen me as a woman, but as a woman worthy of being held.
I could blame my being trans for Jack’s ghosting, but maybe it had nothing to do with that. Maybe he hated his job. Maybe his family fell apart. Maybe the pleasure we felt together contrasted whatever pain remained of our baggage.
On lonely days, I imagine myself at SUNY Potsdam. At a frat party, I drunkenly dance across from Jack, cheap blue lights grazing the curves of our cheekbones, sweat dripping like cyan fireflies. Neil Diamond’s “Sweet Caroline” roars through the party. “Good times never seemed so good,” everyone shouts. “I’ve been inclined to believe they never would.”
I put myself in the cafeteria, where Jack and I approach the salad bar at the same time. When he sees me, he steps back and says, “You go first,” with a grin so big I would need both hands to hold it.
Denny Agassi is a writer, actor and musician living in New York City.
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