How My Sugar Baby Guided Me in Supporting a Friend’s Gender Transition Respectfully

Bridging age gaps is often more complicated than understanding pop culture references and explaining the new slang. Birdy and her sugar daddy, Pat, learned how important empathy and patience are for finding common ground between generations.

Birdy, sugar baby, 25

For my sugar dating life, I identify as a femme, straight woman. And I’m perfectly happy with that persona. I like dressing up and getting my hair and nails done. I fully embrace the role of “ princess,” allowing my sugar daddies to take me on dates and treat me like royalty.

It’s funny, though, to imagine what my sugar daddies would think of me when I’m not on a date with them. In all likelihood, they wouldn’t even recognize me. My everyday attire is somewhere more along the lines of Billie Eilish in her skater boy era. I love playing around with out-there hairstyles and makeup. I hang out with my friend group, which is mostly queer fashion students (a demographic that is staunchly anti-gender norms).

I love jumping back and forth between these two worlds. It keeps things interesting. It’s fun. It allows me to explore different parts of myself.

I know, though, that my sugar daddies tend to be more close-minded, so I don’t tend to share that other part of myself with them. To be honest, I can just picture them jumping on the idea of me being bi-curious as an excuse to suggest a threesome with another sugar baby. And, I’m just not there, you know?

The other thing is, I don’t have any desire to be any old man’s educator. If I’m on a date with someone and he goes on a rant about cancel culture or how he’s glad to be dating a girl like me who “isn’t like the other girls my age who reject traditional gender roles,” I’m staying quiet. I know who I am, and I know I’m not going to change his mind, and it’s not worth the stress.

At least, that was my policy before the whole thing with Pat.

Now, Pat is one of those men who has been through war or whatever, so he feels like no one can tell him anything about being a man. Okay, fair. He has a ton of unaddressed trauma that he doesn’t talk about and pretends doesn’t affect him. But like, I’ve been there when he wakes up drenched in sweat. I’ve felt his hand tighten around mine when he hears a far-off car backfire. So, I know that he’s a feeling, sensitive guy deep down.

Anyway, around the time that we had been dating for close to a year, I felt like we had a good rapport. But we never talked about politics. We never mentioned what my life was like outside of our dates. When we were together, we watched old movies, danced tango, and ate at Michelin-star restaurants. I wasn’t about to rock the boat for any reason.

I noticed, though, that Pat was down for like three dates in a row (the better part of a month). He wasn’t as chatty. He was more tired than usual. Sorry, but I thought maybe it was something medical. He was getting up there, after all.

When I asked him if he was doing okay, I expected that he was going to brush me off. But he opened up pretty quickly. Said that he had a falling out with an old friend. When I pushed a little harder, the floodgates opened.

He said that this friend, Stan, someone he had worked with for years before retiring, had told him that he was finally ready to make the transition to live as a woman. Pat was beside himself. He felt like his friend had been brainwashed and was making a mistake. He said that he couldn’t understand why his friend would want to spend money on something so stupid and actually risk his health.

“Hormones!” Pat cried. “He’s actually going to start taking hormones! Do you know how insane that is at our age? And what, he’s going to start dating men? Is he going to try dating me? I shared a locker room with this man for years. I allowed him to stay in my home. I trusted him.”

Listening to Pat was tough. I could feel my heart tighten and my stomach drop. I didn’t want to validate any of the ignorant and hateful things that he was saying.

At the same time, I could hear such deep-seated pain in Pat’s voice. There was something under the facade, here. So, I allowed him the space to talk himself out. I didn’t nod or approve of anything he said. I just listened.

Once he had talked himself out, Pat looked like he was actually on the edge of tears. He seemed to remember that there was someone in the room with him, and it made him self-conscious.

“Oh, I know what you’re going to say,” he said defensively, “This old geezer is a bigot. He doesn’t know what he’s talking about. Your generation is all mixed up. You’re used to this. But it’s not right.”

“Actually, I was going to say,” I said slowly, “that I’m sorry you feel like you’re losing your friend. That must be difficult.”

“I don’t feel like I’m losing him, I am losing him.”

“Hmm, I wonder about that. You might find that he’s not actually all that different than how he’s always been. Only, he’ll go by a different name. And he might be happier.”

That’s when Pat kicked me out. Fair enough.

Pat, sugar daddy, 73

Of course, Birdy didn’t deserve to get kicked out. She hadn’t done anything wrong. She had listened to me and then asked a question. It was the question that bothered me. I was worried that she was right. It’s exactly what Stan had said during our last conversation: “I’m not a different person than you’ve always known. I’ve just been living with a mask on in front of the world. I’m ready to take the mask off and be happy.”

The truth is, I was deeply hurt about the whole thing. I’m too old to take change gracefully. I want things to stay the same.

That night, I called Stan for the first time in a month. When he answered, he sounded tired.

“You sound like crap,” is the first thing I said to him.

“I feel it,” he responded. “Wanna go get a beer?”

So maybe things weren’t going to be so different after all.

Stan showed up wearing the same clothes that he always had. But his hair was getting long, and I noticed that he had earrings in both ears. In the eyes, he looked worse than he sounded in person. But also, in a different sense, a little better. It was strange. I asked him about it.

“Well,” he said, “It’s been tough to tell people about the changes to come. Lots of people reacted as you did. So that’s been lonely. And hard. There are also some medical things I’m going through that aren’t easy. But I’m going through them. Overall, though, I’m feeling…free. That feels good. I’m sleeping pretty well. I’m meeting new people, people who get it.”

We sat in silence for a while. Just like old times. I asked if he had watched his team lose at the Super Bowl (my team had won and I had been disappointed not to be able to tease him about it at the time). Stan laughed and said he turned off the TV during the fourth quarter.

We finished our beers, paid, and walked out to the parking lot.

Stan thanked me for coming out, “You don’t know how much it means to me to have an old friend right now.”

I grunted, not in approval but not in a dismissive way, either. I told him I’d be in touch when I was ready.

I called Birdy when I got home. She was understanding, but I think also a little bit pissed off that I had treated her the way I did. So, I had to make an apology and tell her that she was right. She seemed genuinely touched that I had seen Stan.

“I have an annoying request,” I told her, “and if you rub it in my face, I swear I’ll hang up.”

She told me to go on.

“I was wondering if you might…help me with this. I want to stay friends with Stan. But I don’t know how. I don’t know what to call him. I don’t know what to expect.”

“Well,” Birdy started, and I could already hear her smiling, “You might start with learning her name and asking about her pronouns. Don’t you worry, it will feel more comfortable as you go. I’ll help you.”

And that’s how I managed to fix my oldest friendship and my sugar relationship in one night. There were many more months of missteps and frustrations, and wanting to give up. But none of us ever gave up. And the three of us are doing just fine with the changes.