After We Broke Up, My Ex-Girlfriend Became My Ex-Boyfriend

transgender dating
Daniel Fishel/Thrillist
Daniel Fishel/Thrillist

Between the ages of 16 and 22, I enjoyed romances with a diverse roster of lovers ranging from a man who was 18 years my senior to a young woman we'll call Olivia, who was two years younger than me and my best friend. 

I'm engaged to a man now, but I've always known I was bisexual. I naturally just fell in love with people regardless of gender, creed, or religion. Chalk it up to the freedom of a New York City upbringing and the enlightenment of all sorts of areas of philosophical study; but I have always been very comfortable with the fluidity of my sexuality.

When Olivia broke up with me (on our six-month anniversary and one week before my birthday, but who's counting) she cut off all communication. It was months later that I found out Olivia was now Oliver -- and that my ex-girlfriend had become my ex-boyfriend.

I was too busy trying to "fix" my girlfriend to notice her shifting identity

I saw Olivia as a fixer-upper. She had no resumé at all, was coasting through design school, and flitted between jobs. No problem; I could help! In hindsight, I treated her more like my protege than partner.

I took Olivia shopping and bought her makeup. She said she liked feeling pretty; and proudly donned colorful blazers, applied eye shadow, and seemed to relish exploring her feminine side.

But while we were together, she often said things like, "I wish I had a penis" or "It must be nice to be a dude." Because we live in a society where it isn't unusual for a woman to hate her body, it sounded normal enough to me.

Gender awakening is not necessarily something that happens all at once

"What woman doesn't occasionally think it must be nice to be a dude or have a penis, like every time you have to pee on a long car trip or camping trip?" asks Diane Anderson-Minshall, co-author of Queerly Beloved, a book about Diane's relationship with a transgender man. Jacob, formerly Suzy, transitioned 15 years into his marriage to Diane. The two have now been together more than 25 years.

Diane says Jacob, similarly to Oliver, was his most feminine right before he transitioned. "You can see old photos of us, and he's wearing men's suits and a buzz cut our first year together," Diane says. "But right before he transitioned… he's wearing capri pants and belly tees and a ponytail."

Because he felt so secure in his masculinity while still living as Suzy, Jacob (then a park ranger) was equally comfortable if Diane, as she puts its, "Barbie'd him up." Suzy was, after all, a stereotypically hot, blue-eyed blonde.

Diane posits that my experiments gussying up my girlfriend likely sped up Oliver's gender awakening because it was a chance to try on femininity and ultimately choose masculinity.

When it comes to the matter of just how "normal" it is for a woman to be critical of her own body, that's what Jacob's first few therapists thought, too. No one understood it, until Jacob did.

What matters is this: People are always changing

From the day we're born to the day we die, we're in flux. People are always discovering new things, absorbing new information, and adjusting their preferences. How we identify, and what we claim as being intrinsically "ours," changes. Significantly.

Had Olivia wanted to transition while we were still together, I would have supported it. My girlfriend was a gentle, nurturing person. And that wouldn't have been changed by a pronoun, body part, or new wardrobe.

"Most people focus on Jacob's gender transition as this huge change: He was a woman, and now he's a man," Diane says.

"But I've gained and lost 200lbs during our marriage. He's changed careers three or four times; I've owned three media companies. We raised foster kids, went through a miscarriage, decided to become childless. His gender reassignment was tough for a spell. But in retrospect, it's just a blip. Today, neither of us is the woman we were in 1990. And for that, I'm actually grateful."

As for Oliver, we haven't spoken since our relationship ended. I can only assume he is also grateful to have evolved from the person he once was. And in the absence of knowing, I can only hope that whomever he is with now sees him as complete: not a project, not in need of fixing, and not anything but exactly who he needs to be.

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Helaina Hovitz is an editor, journalist, author, and media startup co-founder living in New York City.