Discovering My Sugar Baby's Hidden Talent: A Game-Changing Perspective Shift

I’ll be the first to admit that as a man in my 40s, there’s a lot about people in their 20s (Gen Zers, I guess we’re calling them now?) that I don’t connect with. The whole TikTok dancing thing and recording videos of yourself talking while putting makeup on and using insanely informal language on emails—I just can’t help but shake a virtual fist at them. And for a long time, I wrote them all off as naive and totally helpless.

Taylor, of course, changed all that. Actually, when we first started chatting online, I didn’t believe that she was really 25. I figured she was probably at least 32 but didn’t think that she would be able to find a sugar daddy unless she said she was mid-20s. I mean, that’s how worldly and mature this girl was (okay, she would punch me in the arm for calling her a girl instead of a woman, sorry Taylor!)

On our first date, she did look young, but I still didn’t believe it. I even kind of grilled her a little bit about it. I asked her what kind of music she listened to in high school, what she thought of 90s fashion coming back, and what the first movie she ever watched was.

She kind of narrowed her eyes at all these questions and said, “Do you think I’m lying about my age?”

I was kind of dumbfounded. I thought that I was pretty smooth and making seemingly innocent conversation. But she saw my intentions right away. So I came clean.

“You just don’t really fit the mold of what I thought a 25-year-old would be like.” Admittedly, all the sugar babies I had before were in their 30s.

“Why, because I can carry a decent conversation?”

“Well, yeah,” I said. I pointed to her purse. “Like, the fact that you haven’t taken your phone out a single time during our date is not really typical for your generation.”

I could tell that I was starting to walk on thin ice.

“I get it, though,” I was backpedaling. “I do. You guys grew up with phones in your hands. It’s normal for you. Honestly, I’m kind of surprised that you’re able to hold eye contact so well; you’re not distracted. As you guys would say, you’re ‘locked in.”

“Well,” she said, trying to hide her annoyance at this old guy making assumptions about her, “I’ve had some practice. I have a podcast.”

Oh, here we go, this generation and their podcasts. But I was trying to be friendly, so I asked her about it.

“I interview people. The idea is really simple. It’s always a stranger, a friend of a friend, or sometimes a person I’ve met just that day at a coffee shop or on the subway. And, we set a timer on the clock for an hour and see how much they can open up. Then, usually I have a segment for people who have written in looking for advice or whatever.”

It actually sounded much more profound and interesting than I would have expected from someone so young. I asked her where she got the idea.

“Well, a lot of the podcasts out there are interviews with famous people like celebrities or influencers. And, to be honest, I find those kinds of conversations boring. It’s not very fun to listen to someone with such obvious media training or an agenda that they’re trying to push, you know? So, I came up with the idea to do it with normal people, or at least, not famous people. And it really changed my life. I’ve met really interesting people and I’ve gotten better at interviewing in general.”

We talked more about how sugaring had become an extra source of income so that she could invest in better equipment and sometimes offer to buy lunch for the guests. When she had a very good sugaring month, she would pay for an editor and an assistant, which was great because she was getting a bigger following.

“You should be on, actually. I think it might change your perspective.”

I told her that I was flattered but not very interested in being a guest. But I was fascinated by the concept and would like to watch, if that was allowed. For what was feeling like the millionth time that night, she said no.

“I want to respect my guests by giving them a safe space to open up,” she explained. “Having someone else in the room, I think, would throw things off. But how about this? I’ll send you an unedited version of my last interview so you can see what it’s like.”

Throughout this whole conversation, I was realizing that if this girl really was 25 like she said, I might have to rethink my assumptions about this generation. She was light years ahead of what I was like at her age.

That night after our date, Taylor sent me the raw footage from her podcast, as promised. I was knocked out of my chair. She had this unbelievable talent for making her guest feel comfortable. And she was a brilliant interviewer. I mean, she asked all the right questions; questions that I would never have thought to ask but that kept the conversation flowing effortlessly. She was charming and sweet. And sometimes she even teased the guest, and it was amazing to remember that she was talking to someone she just met.

As soon as I was done, I sent a message to Taylor and said, “I don’t want to be a guest. I want to be a sponsor. I want to fund it.”

“Nope,” she said, “I mean, yes, I would love to have you as a sponsor. But, no, I mean, you’re definitely not getting out of being a guest in that case. I think it’s more real that way, and I always want this podcast to be genuine.”

It’s been a year and a half since my episode of the podcast and becoming a part of Taylor’s team, officially. But, actually, she didn’t need me after about 6 months because her podcast got picked up by a big-name podcast network.

Once things took off, Taylor didn’t have quite as much of a need for sugaring as she had when she was first starting out. So, our relationship did slow down, and it was totally without drama or bad feelings. I was honestly so proud of her for everything she had accomplished in such a short time.

I told her during one of our last dates that spending time with her really opened my eyes to my own blind spots about people in their 20s not being serious or motivated. Her talent and integrity surprised me, not because she was necessarily different for her age, but because I had written off her generation before meeting her. So, she really did me a great service and I am a lot more open-minded thanks to her.