From Mentor to Partner: How Learning New Skills Strengthens Our Sugar Relationship

This is the story of how I taught my sugar baby how to lie, how she taught me to speak Spanish, and how we both learned a thing or two about empathy.

My sugar baby, Karina, is a good example of how sometimes it’s okay to lie on your resume. After all, she’s beside me right now in our condo in Cabo, getting dressed in clothes that I bought her so that she can go to a nail appointment that I’m paying for. It all worked out, is what I’m saying.

But that was only after a huge fight, and both of us were thinking that we’d never see each other again.

Anyways, context. I was living in New York at the time, working as a restaurateur. Basically, my job was flipping restaurants. I would find one that was struggling, buy them out, usually fire and completely replace the staff, and then sell it to someone rich who wanted to live the dream of owning an NYC restaurant without having to go through the stress of starting from nothing.

I won’t get into the details, but you can imagine that it’s a job with really long hours, lots of stress, constant dealing with unsavory people (ornery failed restaurant owners, chefs who don’t want to be pushed out, contractors, inspectors, potential buyers looking to lowball, the list goes on and on.) So, I had zero time or energy to date the old-fashioned way.

Sugar dating always made a whole lot of sense for someone like me. For the last four years or so, I would find someone who was interested in living with me part-time, who could cook, clean, take care of my wardrobe, walk my dog, all of that. It was a great gig, honestly, and I never really had trouble finding anyone.

But the last sugar baby left because she wanted to move back to the Midwest to be with her family (New York City isn’t for everyone), so I was looking for someone new. That’s how I found Karina.

Now, I was very clear about what kind of arrangement I was looking for. I needed someone with lots of experience cooking home-cooked meals. It might seem like an odd request, but you spend enough time in restaurants, and the last thing you want is restaurant food night after night. I’m saying this was a big non-negotiable for me. Whoever I found needed to cook. And Karina said she did.

So, we have our first meet & greet just to get to know each other and talk a little bit more about what this would look like if she decided to become my sugar baby. She was super enthusiastic, and so was I. I’ve been in this business long enough to know a good quality person when I see one. And Karina was smart and funny. Additionally, she was Puerto Rican and worked part-time as a Spanish teacher for adults, which was a huge plus since I was considering possibly flipping a few restaurants in Mexico later that year.

And then, we got to the conversation around cooking. And, it only took me a couple of minutes to realize this woman was lying to my face about her experience in the kitchen. Now, I’ll admit that I get kind of satisfaction when I get the chance to call someone out on a lie. I mean, it happens all the time in my line of work. And if I didn’t find it kind of entertaining, much of my job would just be soul-crushing.

So I say, “Hey, you know what? I’d love to get a taste of your cooking before we move forward. The kitchen is about to close. Why don’t we head back there, and you can show me what you’ve got?” I forgot to mention that I plan all of my first meet & greets at restaurants I’ve flipped where I have a good relationship with the current owner. A perk of the job!

I saw the color drain from her face. But, I have to hand it to Karina, she wasn’t about to back down. We went into the kitchen, and I suggested that she make something fairly easy, like an omelet. Of course, an omelet is actually a deceptively difficult dish to make if you don’t know what you’re doing. Most amateurs end up with a mess of scrambled eggs. Which is exactly what happened to Karina. A soggy, over-salted, stuck-to-the-pan mess.

“So, what?” I asked. “Were you just going to sneak delivery in and then hide the boxes? What was your plan?”

Clearly angry, she brought the skillet of scrambled eggs over to the trash and threw the whole thing—skillet and all—inside. Then she said something in Spanish to me that I can only imagine meant something like, “I hope I never see you again.”

I went home, a little bit smug but more feeling disappointed that it didn’t work out. I really liked Karina. And a couple of hours later, I get a voice message from her that I still have saved in my phone:

“Hey, look. I’m really sorry for leaving like that. And obviously, I’m more sorry for lying. The truth is that I never learned how to cook because I grew up with my uncle. My mom passed away when I was a kid, and my dad is still in PR. And my uncle worked, so he never really had time to teach me. The best I can do is rice and pasta, sandwiches, easy stuff. I know that you probably don’t ever want to see me again, but I just didn’t want you to think that I’m lazy or something like that. Honestly, being in the kitchen always reminded me of her, and it would make me sad. So yeah, that’s it, I guess. I just wanted you to know that.”

I slept on it, but I knew pretty quickly that I was back on board. I mean, who among us hasn’t lied in a job interview or on a first date to try to impress someone?

I called her and said, “Look, if you’re going to lie on your resume, you should at least know how to convincingly make an omelet.” And so we set up a date for that night, back at the same restaurant, and I taught her how to convince anyone that she knew how to cook with one simple plate.

Now, obviously, we’d have to work out some things if this was going to be worth it. The home cooking thing was non-negotiable, so I ended up hiring an at-home chef who could teach Karina how to cook for a couple of months, and we evened it out with Karina teaching me Spanish three times per week.

And as I said, here we are in Cabo. It all worked out even better than I thought it would. Karina has been helping me with the restaurant renovations. She’s essential in working with the contractors, and when it comes to negotiations, we’re a pretty good team. She’s been able to keep her part-time job teaching Spanish to expats living here in Cabo.

And if you were to force me to think a little bit deeper about what skills we’ve both learned since Omelet-gate, well, I could point to a lot. I, obviously, felt bad about putting Karina to the test during that first date and have learned that I don’t have to be so right all the time. And, learning Spanish has taught me patience, of course.

On Karina’s end, who knows? Like I said, lying on her resume worked out pretty well for her! Haha! But in all seriousness, being vulnerable and telling me about her mom was a big turning point for her. And we wouldn’t be here if she wasn’t willing to get back in the kitchen and learn how to build a new relationship with cooking that celebrates her mom instead of focusing on her loss. We’ve both softened a bit, and that’s been good for our relationship!