Mastering the Art of Long-Term Sugar Relationships

Wondering how to make sure that your sugar relationship goes the distance? Take a look at this story from Calvin and his sugar baby, Sandra, to learn about how to build a connection that lasts!

Calvin

I used to be the kind of sugar daddy who would cycle through a new partner every couple of weeks. I enjoyed the excitement of meeting new people. And I tended to go for sugar babies who I knew would probably naturally want to move on quickly anyway. My sister would give me all kinds of grief for my “revolving door of hot young things,” as she would say. This phrasing always bothered me to no end (just because our relationships were short-lived didn’t mean that I was treating them as “things), but anyway, there wasn’t much I could say.

Then, I bought a new house, and truly, it was the house of my dreams. I had been a homeowner for many years at that point, but this one felt like “the one.” I worked with an architect to design it to my taste and lifestyle. I had a huge housewarming party that lasted all through the night and part of the next day. I mean, I really felt like I was living large.

And then, Thanksgiving came, and my sister insisted that I host since the family wanted to see the new place. And suddenly, for the first time in my life (I was 45 at the time), I felt a kind of pang of regret that I would be hosting as a single guy.

It’s not like I had any kind of dreams of being a family man, so it was a surprising feeling. I talked to a buddy of mine about it, and he suggested that wanting companionship didn’t have to mean that I wanted a wife and a family, necessarily. He asked me whether I would be interested in finding a sugar baby who could be a more stable fixture in my life. And when I hemmed and hawed about it, he reminded me that it didn’t even mean that I had to stop seeking out new experiences, as long as I was honest with everyone involved about what the situation would be like.

And it sounded okay, actually. So, I updated my bio, and along came Sandra.

When I met her, Sandra was sugaring as a way to save up money for a down payment on a house. She said that she was hoping to be with someone for the next two years, and then once she had found her dream home and put down the deposit, she would stop sugaring.

I thought this sounded like a great middle ground for me. I wanted to try something long-term, but I had been worried about meeting sugar babies who were obsessed with the idea of getting married eventually. Sandra, though, seemed like she would be able to do something long-term, but without expectations of things becoming more serious.

Well, I guess when you’re talking about long-term relationships, there’s not really a way for things not to get serious. And, I can’t say that I was ready for that. But Sandra is persuasive and patient. And if anyone was going to get me to come around, it was her. But I’m going to let her tell that side of the story.

Sandra

I absolutely knew that Calvin wasn’t ready for a long-term sugar relationship. He had told me about his previous dating habits and how no one had lasted long enough in his life for him to form a real connection. To be frank, it was a red flag for me. I almost said no. But when he told me that story about hosting Thanksgiving and being sad that he didn’t have a woman in his life to share that experience, I felt like, okay, there’s potential here. And hey, potential might not be enough for love. But I think it’s enough for sugaring. So, I gave him a chance.

The first month was a breeze. He was the perfect sugar daddy: he planned dates, arranged for a car to pick me up, and he always wanted to impress me by ordering the nice wine and whatever dessert I wanted. But listen, I knew what his track record was. So, I knew that this might not last. I expected him to get bored or maybe pick a fight that he would be able to use as an out to end the relationship. I was ready.

And then it happened. We had our first fight. It was a miscommunication thing. I don’t really remember the details, but I think it was something like he had arranged for a car to pick me up at a certain time, and I told him that it conflicted with my work schedule. And, either he had forgotten to tell the driver or had forgotten that I had said that the time didn’t work for me, or something like that. Anyway, whatever it was, I got an angry text that I didn’t see until an hour later because I was at work. But it was basically chewing me out because the driver charged him for the ride even though I never showed up.

Now, I had been preparing for this moment, and I kind of knew that Calvin wasn’t going to admit that he had messed up, so I sent him a message that was sweet as pie that said, “Oooh seems like there was a miscommunication between you and your driver since I remember letting you know that I wouldn’t be available until after my shift. If you still want to see me tonight, feel free to book an Uber for 7:30 as we had previously agreed upon. Or, if you need some time to cool down, that’s fine too. I’m happy to check in with you tomorrow to see how you’re doing.”

The way this man folded immediately! He really had expected me to match his energy, and when I didn’t, he had no other option than to admit that he had messed up. Luckily, it didn’t take him long to come around, and he scheduled my Uber so that we wouldn’t miss our date.

Well, I was crafty because I called ahead to the restaurant and had them have two shots ready at our table when we sat down. Calvin looked confused until I raised my shot and said, “To our first conflict, and our first resolution.”

He had to laugh at that.

Now, I don’t want to make it seem like I’m a perfect saint and never did anything wrong. I had to work on my own stuff, like that time that I got mad at him for being on his phone at dinner. which I consider to be a huge sign of disrespect, and it turns out that he was busy booking us a trip to the beach. Or, there was that time that we ran into each other in person and he pretended not to know me because he was with a colleague and I had to remind him that we were essentially dating for the next couple of years and he would have to start treating me as such, otherwise he could go back to dating a new sugar baby a week. You get the picture. We had stuff to work through.

But what always helped me was that story about Thanksgiving and reminding myself that Calvin really is a good guy; he just never had to consider another person in his life.

Let’s fast-forward to the following Thanksgiving, which we had at Calvin’s place with his family. By this point, we had ironed out a lot of the issues that we had had at the beginning of our relationship, and he felt comfortable introducing me to his family as a girlfriend. The evening went off without a hitch. I got along well with everyone, even though I’m pretty sure they knew what the situation really was.

Once everyone had gone home and I was about to head out to run over to my own family’s Thanksgiving, Calvin gave me an envelope. Inside was a check for the amount that I still had to save up for a down payment.

“Are you breaking up with me?” I asked him playfully.

Always a gentleman, he said, “I want to keep this going as long as you’re still interested. But it felt weird feeling like you were chasing some carrot on a string. So, I’m leaving it in your hands. If you’re ready to call it quits, I’ll respect your decision. If not, I’m here.”

I took the check, but I told him, “Well, obviously, I’m going to need your help picking out my dream home.”

That was about four years ago. And no, we didn’t end up getting married and moving in together. In fact, we both ended up meeting other people through more traditional routes and eventually ended our sugar relationship amicably after being together well over two years. Every year, my partner and I are still invited to Calvin’s for Thanksgiving.