From Tension to Terms: Resetting Without Drama

I am not a trans woman, but I respect the heck out of the sugar babies who are. I mean, they must go through some (at best) awkward stuff with these older guys who are genuinely confused when they hear they/them pronouns. I’m not going to say that I get it right all the time, but I can at least understand the concept and try my best not to misgender anyone.

And for sure, I didn’t come across this problem that much in my daily life. I’m a young woman. I date older sugar daddies. There hasn’t been much confusion or conflict. That is, until one of my sugar daddies, Barry, said something that I couldn’t ignore.

We were out to eat at our usual spot, and I was enjoying myself. Barry and I get along great, and we’re super open about everything. He tells me about sugar babies he’s dating. I tell him about guys I have crushes on. It’s all on the table.

But this time, he told me, “I had to break up with one of my sugar babies last week, if I can even call him a sugar baby. I don’t know what the term is for men who are trying to be sugar babies.”

My hackles went up immediately, but I stayed calm and put on my best innocently curious face.

“What do you mean, men who are trying to be sugar babies? Sugar babies aren’t just women.”

“No, no, you know what I mean. Transgender or whatever. He/she. I know your generation is all willy-nilly about this kind of thing. But it’s just disingenuous, is what it is. I went three whole weeks talking to this guy, thinking he was a woman, talking about starting a relationship. And then, on our first date, he mentions that part of his allowance will go towards paying for his transition? That’s when I slammed the money for the meal on the table and left.”

I could tell that Barry was hurt by what had happened. His anger was only surface-level. And I knew that Barry had a history of being very sensitive about deception. His dad had left when he was a kid on the false pretense that he was taking a work trip and would be back in a couple of weeks. Then, his wife cheated on him and lied to him about it for months. He’d had sugar babies who had duped him into paying for expensive beauty treatments only to ghost him before they really got to know each other. All of this stuff added up.

“Did you already block her? Can I see her profile?” I know that his eye roll was for my using her chosen pronouns, but he handed over his phone so that I could take a look. Clear as day, right in her bio, she said that she was a trans woman.

“Barry, I say this with all the love in the world, but she clearly mentions that she’s transgender three times in her bio.” I pointed it out to him.

“Oh, you know I don’t really read those things. Or, he could have put them in after. I feel like he was trying to get one over on me.”

Now, I know that Barry is not looking for a physical sugar relationship with his other sugar babies. He likes companionship. He likes to be seen about town with a pretty girl. If there’s kissing or anything more, it’s rare and never goes very far. So I felt like he could actually be happy with a trans woman if he could get his knee-jerk reaction under control.

“Let me ask you this,” I said, making sure to keep a playful note in my tone so that I didn’t shut him down. “Did you like your conversations with this person? Before you found out?”

“Yes!” he practically yelled it. “Of course! I wanted to keep seeing her, when I thought she was a her.”

Great, this kind of enthusiasm and openness I could work with.

For the next hour, Barry and I talked about what it was about having a trans sugar baby that made him uncomfortable. We talked about why the finding out was such a shock and whether it had something to do with his past. We talked about identity in general.

“Remember, Barry, when I showed you pictures of me in my early 20s when I went through my emo era? Do you remember what you said?”

He rolled his eyes again and laughed, “Yes, I said, thank goodness you came to your senses, or we wouldn’t be here right now.”

I laughed too. “I told you that I went through that phase when I was trying to fit in. I wanted desperately to like it as much as my friends did because I really did love my friends who were emo. However, I never really felt completely comfortable in those clothes or that makeup. It didn’t suit me as it suited them. I was playing a part.”

Barry could see where I was going.

“When I moved away from those friends to come here, I took it as a fresh start. I tried something new, something that felt more like me. And I finally feel like who I am on the outside and who I am on the inside are the same.”

To my surprise, Barry waved his hand. “Yeah, I get your point. I do.”

I could tell he didn’t want to talk about it anymore. But he was brooding. I could see that there were gears turning in that stubborn head of his.

Anyway, we got through the end of our date, and I figured that would be the end of it.

But it wasn’t. The next time I saw Berry, he had a devilish little smile on his face.

“Okay, tell me,” I said.

“I saw Phoebe again, the sugar baby we talked about last time.”

I was genuinely shocked and asked for more details.

“I realized that I was being unfair and judgmental. It was my problem that I didn’t read the profile. And I thought, ‘Why don’t I give this one more shot and see if I’m really against it or if I can get past it?’ So we met for coffee.”

“Did you apologize?”

“I apologized, yes. I told…her…I wanted to have a couple more dates to get to know each other and see if there was really a spark or a connection. I kind of thought that at the very least, it would give me a chance to meet someone like her and pick her brain.”

“Oh god, I hope you didn’t give her the 3rd degree,” I teased him.

“No, no, nothing like that. I had questions, yes. But she was very open to talking to me about whatever I wanted to know.”

I squeezed his shoulder. “I’m proud of you. You really opened your mind on this one.”

“Well, to be honest,” he told me. “It was because of our last talk. Anyone else that I had ever talked to about this kind of stuff was always so quick to shut me down or call me a ‘homophobe’ or whatever. You didn’t judge me.”

I was touched, honestly. It was nice to be reminded that these kinds of conversations, the ones that are more playful and curious, could be more powerful than shame and accusations.

“So,” I joked, “If you’re paying for Phoebe’s transition, does this mean you’ll finally support my transition to becoming a woman with a bleached blonde pixie cut?”

Barry looked agonizingly at my long brown hair. “Please don’t. I’m open-minded, but I don’t think that’s a shock that I could take.”