Confidence and Connections: Lessons Learned from My Sugar Daddy

I got into sugaring the way that a lot of women my age do: because I was a broke art school student who was tired of living on ramen noodles and saying no to going out with friends because even happy hour deals were out of my price range.

And that might be why my early sugaring experiences were, well, pretty superficial. I didn’t really know what it meant to be a sugar baby. I just kind of thought that I would show up looking pretty, have a predictable conversation about what the young kids were up to these days, and then walk away with an envelope of money.

I’ll be the first to admit that those expectations made my first few dates pretty miserable. Those poor guys saw through my disinterest right away. And, yes, they paid for my meal (and my way too many glasses of expensive wine.) But I was absolutely not getting asked out on second dates.

I was discouraged, so I went online to read about the experiences of other sugar babies. And, I saw pretty quickly that my approach wasn’t going to get me far in this world. The actually successful sugar babies weren’t just doing this as a side hustle. They were serious. And if I wanted to be successful, I would need to get serious, too.

So, at the end of 2023, I sat down and I wrote out what my goals were after art school and what I would need to do to achieve them. I decided to think big and set a goal to get an artist's residency, really anywhere, but it would be so cool to be sent abroad somewhere. And then, I started tailoring my sugar daddy search so that I could make connections with guys who were interested in art or investments, or business.

And, after a few conversations that fell flat and first dates that didn’t pan out, I met Tim (we’ll call him.) Tim was in corporate law, but he had a private art collection that he had curated over many years. I’ll never forget that our first date ran way longer than I expected it to because we were talking about our favorite artists and some of his most treasured pieces.

He knew that I was in art school, but I hadn’t told him about my post-graduation goals or the fact that I was freaking out that I had sent out a bunch of applications and hadn’t heard anything back. Actually, I was a little bit nervous to bring it up.

But by the end of our first date, he said the words that I hadn’t heard yet in my sugar dating career, “I want to see you again.” I was finally about to get my chance at negotiating a sugar relationship!

Again, I will reiterate that this was my very first time. So, of course, I almost messed it all up.

“I want you to mentor me.” I blurted out.

“Oh, okay,” Tim looked disappointed. “Well, if you’re looking for something platonic, I did say in my profile that I want a more traditional type of relationship. Maybe this isn’t…”

“No no no,” I clarified. “I do want that too. But I’m applying to residencies for next season, and I would like some help with the interviews, and also, if we keep seeing each other and you go to an art auction or something like that, I’d love to be your date and maybe network, although I’m terrible at networking.”

He laughed and pressed his palms down on the table. “I only have one demand,” he said. “When you’re rich and famous, I want to buy one of your paintings.”

Over the next few weeks, Tim and I would get together once and sometimes twice a week, and for the first fifteen minutes, he would ask one single interview question to help me prepare. And then, when we had cycled through those, he asked me to bring in my artist’s statement so that he could look over it, and then my portfolio.

Finally, after about two months of this, he told me he had a gallery opening invitation that he wanted to bring me to. I was so excited and touched that he wanted to bring me as a plus-one, and also incredibly nervous because, as we’ve established, networking is not my forte.

But as it turns out, Tim was already so familiar with my work and my goals by that point that he made the perfect wingman. He introduced me to seasoned artists and art curators, and up-and-coming artists. And yes, I even met a woman who worked at an art center currently accepting applications for artists for their residency program. Tim later said that I kept my cool pretty well, but I think he’s lying.

And, no, I didn’t get that residency. But hey, I did get another one before I graduated from my art program. And even though I wasn’t even selling my paintings yet, Tim bought one at a price that would fund my plane ticket and my first few months of rent.

I think all the time about all of my art school friends who thought that I was “selling out” when I started taking sugar dating more seriously. Well, my entrepreneurial spirit won out in the end, and now I’ve got the confidence to keep working towards what I want my art career to look like!