From Boomers to Gen Z: Bridging the Generational Divide in Sugar Dating

Wondering how sugar babies and daddies bridge the age gap? Take a look at these three stories from people in the Bowl!

Stephanie, sugar baby, 25

I met my sugar daddy while I was waitressing in the financial district of my city. He would come in during his lunch break and ask for me, which I didn’t mind because he was always very nice (and would tip amazingly). Eventually, he asked if I could sit with him just for a couple of minutes after I cleared his plates. I told him that I would get in trouble for that, but would be open to going out with him on my day off. I wrote my number down on a piece of paper and slid it under his plate.

I think this was the first cultural gap between us; he wasn’t used to a woman being so forward. But it didn’t seem like a problem, at least not yet.

Anyway, we went on the date. He took me to lunch at a really nice place with a view of the river. And honestly, I felt really out of place. I was underdressed. I didn’t know about wines. He immediately started talking to me about his job, which I could not understand at all. And, I know that this is terrible, but about forty-five minutes into our date, I found myself checking my phone to see how much time had passed.

“Expecting a call from someone?” he asked. I was mortified.

“Sorry,” I said, “I have a friend who’s going through some medical stuff and I just wanted to make sure that she hasn’t messaged me.” Total lie.

“I think maybe we should just get the check,” he said. We had just barely finished eating. I was filled with both embarrassment and relief.

There was an awkward silence in the car that I kept trying to fill with commentary about how beautiful the view was from the restaurant and how much I liked my food.

He turned the radio up. It was playing a song by Fleetwood Mac that had become trendy recently. I genuinely loved that song and started to sing along.

“I would think you’re too young for this kind of music,” he said. He started to tell me about seeing them play live when he was young, how he dated a girl who had named her dog Stevie.

I started laughing. “Guess who has a cat named Stevie?” I asked and pointed to myself.

For the rest of the ride home, the conversation was fluid and easy. By the time we pulled up in front of my house, I didn’t want it to end.

“Look,” I said. “I’m so sorry about checking my phone at the restaurant. That was really rude. To be honest, I felt really out of place there. I feel like maybe I’m too, I don’t know, uncultured or naive to be a good match for you.”

He waved me off. “I immediately regretted bringing you there. What was I thinking bringing a fun, young girl to a stuffy place for old rich people like this? I thought, ‘she’s never going to want to be seen with me in public again.”

He asked if I wanted to go get ice cream somewhere, anywhere I wanted. I took him and his nice BMW to the nearest fast food drive-thru we could find. We sat in the parking lot trying not to get soft-serve all over everything, and it was probably one of the best first dates I’ve ever had.

Cole, sugar baby, 33

I will admit that I was one of those jerks who thought that life essentially ended after 30. Every person over 30 seemed to complain endlessly about their age, being tired, aches and pains, and the dating scene. It all just seemed like such a bummer that I took my own 30th birthday pretty hard.

Now, I had been sugaring on and off throughout my 20s. But again, because I had this kind of bias towards older people, I’ll admit that I never really made any emotional connections with my sugar daddies. As soon as they started opening up, and especially if they started complaining about anything, I would end things (I know, not a good look, but I was young!)

Anyway, right after my 30th birthday, I revamped my sugaring profile. And mind you, I thought that I wouldn’t get any kind of attention anymore because in my mind, all sugar babies were young, hot 20-somethings. I just didn’t think anyone would be interested in me.

But as it turns out, I started getting attention from a different kind of sugar daddy. They seemed to be looking for more long-term relationships, someone who could attend business events with them, or travel partners. It all seemed a little bit more serious. And on a first date with a sugar daddy who was in his late 50s, I asked him about why he pursued sugar babies in their 30s.

He said, “In my experience, it can be easier to connect with a sugar baby in their 30s. They’re a little bit more settled, more mature. They won’t just ‘ghost’ you. But they’re still open to new experiences. Fun, energetic. It’s worked out well for me.”

His ghosting comment really struck me, I’ll be honest. I had been guilty of that because, like I said, I was pretty self-centered and didn’t want to get wrapped up in other people’s emotions. And, I’m not going to say that every sugar baby in their 20s is like I was. But I do feel that it became a lot easier to connect with older sugar daddies once I had gained a little bit of life experience (you can read that as empathy). As I got older, I was able to listen and connect with partners on a more emotional level, which actually made my sugaring practice more successful and stable. So yeah, I had to do a little bit of growing up on my end before I was ready to bridge the generational gap. But once I did, it made things so much better!

Joe, sugar daddy 63

By the time my own father was 63, he was one of those men who literally would sit on his porch yelling at the neighborhood kids. He was essentially a caricature of a grumpy old man, and because he had me later in life, I struggled to connect with him. I’ll never be like him, I thought.

It’s safe to say that I took a different approach to life. Exercise and especially strength training were always a priority. My blood work always came back with flying colors. I limited my alcohol and stress, and all of the things they say you need to do to stay young.

But there was something that I didn’t realize yet about growing old. It’s not just in your body, it’s also in your head. And I’ll explain what I mean.

I went on a few dates with sugar babies throughout my 50s that were disastrous because I felt like I couldn’t connect with them. But instead of really asking myself why, I just blamed them for it. “These young people don’t know how to have a conversation,” I heard myself saying. Or, “I knew how to show gratitude at their age. Everyone now is so self-centered.”

And on one particular date, when a sugar baby was talking about some political thing that I thought she didn’t know anything about, I let it slip. I said, “You young people are so naive.”

She said to me, I kid you not, “If you’re so angry at young people, maybe you should just go sit on a porch somewhere and yell at us to stay off your lawn.”

It shut me up so fast that I almost choked on my food. I realized immediately that it didn’t matter how young I felt in my body because of exercise and protein powder, and (yes) Botox. I was allowing my mind to get old.

“You’re right,” I said. “I’ve gotten stubborn. Why don’t we start over, and I’ll listen to your side and then I’ll offer my perspective, and we can see if there’s somewhere that we meet in the middle.”

And that’s how I started to exercise my worldview instead of just my body. Now, at 63, I feel younger than I did throughout my 50s because I’m more positive and open than I had been. And it’s not like I never get annoyed with young people, but anytime I find myself writing them off or grouping them all together, I think of that old man on the porch and how much I don’t want to be him.