Short film. Based on award winning story by LGBT fiction pioneer Richard Hall.

Playdates With The Ex

Assorted bottles of nail polish.


I was different as a teenager. I never wanted to look like any of the pretty cheerleaders at my school. Instead, it was my teenage boyfriend’s body that I envied.

He was beautiful. He was Native American and had gorgeous skin. His body was toned but not ripped, and, thanks to genetics, he was virtually hairless other than what was on his head. He had the genitals of a male, but other than that, everything about him screamed female. He was short, only slightly taller than I, and far thinner. He looked like a beautiful, exotic, flat-chested woman with a penis.

We lived a short drive from Tijuana, and we went often. He spoke Spanish fluently, and he would find cheap boarding houses for us to stay in, places that American tourists didn’t know about. At the guesthouse we preferred, we paid a whopping eight dollars a day for a room. There were six bedrooms, three for the family members who resided there and three for their guests, and there was a total of one bathroom for us all. There was no hot water, so showers were quick.

One day, we had just arrived back at our room after getting some lunch. It was unbearably hot, so I went straight into the bathroom to take a shower. It couldn’t have taken more than three minutes. When I walked back in the room, my boyfriend was standing by the mirror, applying the mascara I had left on the bed. He looked terrified.

I walked up to him and gently said, “You probably shouldn’t put makeup on a dirty face. Go take a shower.”

He literally ran out of the room. When he returned, he came back a different person, acting with a machismo that I had never seen. Before I could say anything, he blurted out that I was insane for thinking that he was applying makeup. He was emphatic that he was just cleaning up and that I was crazy for believing anything else.

I said nothing. I was young but fully aware that this was a pivotal moment for us both. Anything I said was probably going to stay with him for a long time. It was still early in the day, and he wanted to go out drinking, so I feigned illness and asked if we could just stay in. He liked to restore vehicles, especially older VWs, so he brought several Hot Rod magazines with him and was sitting on the bed, perusing them. I looked over and gently touched his hand.

“Hey, your cuticles look terrible. Can I clean them up a bit?”

“I don’t care.”

His tone of voice showed that he was still perturbed, but he did move off of the bed and over to the small, rickety set of table and chairs in the corner. Surprisingly, he let me give him a manicure, something he had never let me do previously.

He was fully engrossed in his magazines, so I grabbed the black nail polish out of my bag. For someone who worked on cars daily, his hands were so soft. I painted the nails on his left hand. “What do you think?”

He looked down at his hand and burst into tears. “Take it off! Take it off right now! My dad will kill me if he sees this!” He truly seemed concerned for his safety.

“Baby, can you keep it on, just for 10 minutes? That’s all. I’ll remove it in ten minutes. Okay?”

He was livid, but he agreed. He just sat at the table and looked at the clock for those ten minutes without speaking to me. Panicked, he said, “Ten minutes are up.”

I went over, straddled his legs, and sat on his lap facing him. We sat like that a lot when we were alone. It made a kind of safe space for us. “Hey, it’s okay.”

He shook his head and contorted his face. He would not look at me. Tears were streaming down his cheeks. “Why are you trying to turn me gay? I’m not gay.”

“No, you’re not. But you like girly stuff, and that’s okay. We can do this stuff when we’re alone.” Oh, how I wished that I knew of the term “genderfluid” at that time. It was infuriating for him not to have a word to put to what he was experiencing.

We stayed in Mexico for three more days, and during that time, we barely left the room. I watched him struggle to come to terms with who he was. He was in pain, knowing that if his family knew, he would be a great disappointment to them.

I stayed with my boyfriend for years after that. We went off to college together, continuing our “playdates,” our word for his times as a girl. And even though we didn’t have much money, we made sure to take small day trips to places where no one knew us so that he could go out in public as “Roxy.”

After graduating from college, I applied for a job teaching English abroad. He was terrified of my leaving, of having to live without the one person who allowed him to be who he was. My heart ached for him, but I knew that it was the best decision for us both. Had I stayed, we probably would’ve been together forever. But we needed to grow. So we made a pact that I would go away for one year. If we were both unattached when I returned, we would pick up where we left off.

Twelve months later, I returned and was introduced to his boyfriend. Yes, his father had disowned him, but he looked happy and healthy, and that was all I had ever wanted for him.

I don’t know where my ex is today, and that’s okay. We kept in touch for a while, but we’ve both moved around a lot. I’ve done searches for him and questioned people we both knew. No one has seen or heard from him in years. But I’m not worried. I’d like to believe that they have transitioned, living an authentic life, and have taken on another name, one that truly fits.


DJ Tombe is the author of The Bunny Trail Series, which consists of three Young Adult LGBT+ books including the theme of gender fluidity. The three book titles include The Bunny Trail, Thou Wilt Go Now, Rabbit, and I Go With Thee.


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