A Short List of the (Often) Underwhelming Men I’ve Encountered as a Trans Woman on Dating Apps

Introduction

Welcome to Love Transcends, a special project by Cosmopolitan celebrating the resilience, wisdom, hope, and joy of the trans community as they navigate romantic relationships. Through interviews and personal essays, trans individuals share their experiences of dating, breaking up, and finding love amidst challenging times.

Transitioning and Dating

I have always been part of the LGBTQIA+ community, but about six years ago, I transitioned from “G” to “T.” Before transitioning, dating men felt natural and fulfilling. Being a gay man allowed me to connect deeply with my partners through shared experiences. However, after transitioning, I struggled to let go of that identity. Attempts to date other trans women didn’t work out, and I realized I was a straight woman navigating a world dominated by heteronormativity, with unfamiliar dynamics and references.

Exploring the Online Dating World

Venturing into online dating, I encountered the hypersexualization of trans women, especially on apps. Initially, I thought these interactions might lead to real relationships, but they mostly resulted in superficial encounters. The men I met online fell into a few distinct categories.

The Actor

One day, a blank profile contacted me on Grindr. The man, who I recognized as an actor from a show I had watched, was handsome and intriguing. Despite his charm, our interactions were brief and secretive, as he didn’t want to be publicly associated with a trans woman. This experience highlighted the challenges of dating in Hollywood, where there is little to gain for men by openly dating trans women.

The Poly Musician

Another encounter involved a poly musician who forgot his wallet on our first date, leading to me covering the bill. Despite the initial awkwardness, we ended up spending the night together. However, his subsequent behavior at a coffee shop with my friends revealed his chaotic nature, prompting me to end things.

The Malibu Daddy

By the time I met my first Malibu Daddy, I was familiar with the anxiety that comes with being fetishized by chasers. Despite the chemistry and his wealth, the relationship was transactional, with him flaunting his status while being stingy. This experience taught me not to invest emotionally in such encounters.

Reflections and Moving Forward

Being treated like a delicate flower or catcalled felt affirming, but it soon became clear that this kind of attention was superficial. The fear of violence or rejection loomed large if I didn’t conform to certain expectations. This realization made me take a break from dating apps, seeking dignity and genuine connections in my real life.

A New Beginning

After a period of self-reflection, I decided to try Hinge again. To my surprise, I matched with a finsexual guy who was genuinely interested in me. He was thoughtful and considerate, even remembering my dietary restrictions. Our date was wholesome, and for the first time, I felt my dignity growing. I am hopeful about the future and the possibility of finding a meaningful connection.

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