Embracing Simplicity: My Secret to Sugar Dating Success

One year, my New Year’s resolution was to “work on myself,” so I decided to try a crack at therapy. Well, suffice to say that it didn’t last long. I guess I was a bit of a difficult patient. But, I just couldn’t help but roll my eyes when this woman, scribbling in her notebook while I spilled my guts out (a woman who was younger than me, by the way), told me that maybe I was responsible for my failed marriage and the subsequent string of relationships that ended poorly.

According to my therapist, I was choosing women who were “emotionally unavailable” and “looking for drama” because my parents hated each other. I was overcomplicating things because complicated was what I was used to. And when I did actually find a partner who was even-tempered and normal, I ended it because I got bored. But, instead of being bored, she said, what I really was was scared to form a healthy emotional connection.

This take of a licensed professional, in my opinion, was a bit of a stretch. What did my parents have to do with the fact that most women these days are either shallow clout-seekers or entirely without a personality? Maybe I’m a bit picky, but I didn’t think I was a complicated man. In my view, back then, I just was not willing to settle for anything less than my dream girl. And if I had to cycle through shallow relationships, blind dates, and the occasional messy ending, so be it.

Maybe it’s in bad taste to break up with a therapist after three sessions, but I was pretty used to break-ups at that point.

Cut to three years later, and I had discovered what I thought was the solution to my dating problem: sugar dating. And, to be fair, it did turn out to be the solution, just not in the way that I thought at first.

Basically, what appealed to me about sugar dating was that it was simple. I could find someone I liked. We would come up with an arrangement that worked for both of us. And if there was even a whiff of drama (or boredom), then it was onto the next. No hard feelings. No messy breakups. I wished I could call up that therapist and say, “See? I’m a simple man with simple needs.”

But then I met Sadie.

Now, it’s not that Sadie was some saint who came in and showed me the light. She had her own blind spots and quirks and was the lightest of lightweights when it came to alcohol that I had ever seen. But she was also far more grounded and even-keeled than anyone I had ever met. And smart as a whip. And physically…Well, I won’t go there. I was smitten. That’s all I have to say.

By the time I met Sadie, I had already been sugar dating for a while, and I had a few rules. First, because I was an entrepreneur with a public image, I needed an NDA. There were also a few guidelines about posting on social media, being seen together in public, exclusivity, intimacy, etc. Oh, and agreements always had to be renegotiated after a three-month period. Most sugar relationships didn’t make it past a second renegotiation, which was how I liked it.

When I explained all of this to Sadie, she had an amused look on her face.

“A bit more complicated than I’m used to,” she said, smiling. “But, I’m pretty easygoing. I think we’ll get along great.”

I’ll admit that the word complicated stirred up that same feeling I had in the therapy session. Part of me wanted to end it right there, but then I thought, “Well, that would just prove that therapist’s dumb point.” So I set up another date with Sadie.

Sadie, as it turns out, was right. We got along great. More than great. Our time together flew by. I hardly ever wanted to say goodbye at the end of our dates. I had to keep myself from calling her throughout the day, and I even kept a list of things I wanted to remember to talk to her about in my notes app.

There were times that I thought, “Is this the dream girl?”

This was also around the time that I started overthinking. If Sadie showed up to a date a little bit distracted, I assumed it was because she was getting bored with me or had already started seeing someone else. If she didn’t react exactly the way I expected her to when I got her a gift, I told her that I would rather just return it than see her pretend to like it. I split hairs, I overanalyzed her words and gestures.

Finally, she put her foot down. I had told her that I had gotten a reservation at a place we had been talking about for a few weeks, but the timing didn’t work for her. She suggested an hour later (which was our normal timeslot), and I told her that maybe we should just cancel the date and try to make something work the next week.

Was it a tantrum? Looking back, I can see how it probably was. Sadie recognized it immediately, but she didn’t take the bait. She also didn’t let it slide.

“Sorry to hear that. I was looking forward to seeing you this week. I can only make our normal timeslot work if you’re free. That is, after all, the agreement we made, and I have that time blocked off for you. But if not, sure, let’s try again next week and see if we can make something work.”

I didn’t respond. She didn’t follow up.

Maybe karma was on Sadie’s side because on the day that we were supposed to have our date, I got very ill with food poisoning. I was probably feeling kind of lonely and pathetic, so I sent a message, something along the lines of, “Our date wouldn’t have worked out anyway. I’m homesick with food poisoning.”

Sadie responded immediately to let me know she was sorry to hear about the food poisoning. She also told me that she would love to bring over a care package if I didn’t mind. Even though I hadn’t talked to her, she had kept our normal date time free. I was of two minds about it, but I said yes. Deep down, I wanted to be cared for. We’re all a little weak when we’re sick.

It was a Friday, and Sadie showed up at my doorstep with soup, movies, electrolytes, and noise-cancelling headphones.

“What are the headphones for?” I asked.

“Those are for me, to give you some privacy when you need to use the bathroom,” she was laughing in a way that I couldn’t say no to. I let her in, and she proceeded to take care of me the whole weekend.

But, as much as that therapist might have been delighted to hear it, I wasn’t done with my drama, just yet. After that weekend being taken care of by Sadie, I decided to end it with her. Things were just getting too complicated, and I was a simple man with simple needs. I didn’t want a girlfriend. I was done with messy breakups.

When I sat Sadie down to give her the news, though, she gave my knee a squeeze and said, “No, I don’t think so. Our agreement isn’t over for another six weeks. It’s not complicated. You agreed, I agreed. Neither one of us has done anything to break that agreement, at least I haven’t.”

I was momentarily speechless, so she went on.

“I think what’s happening is that you’re feeling weird about how well things are going between us. I get the sense that this might be the first healthy relationship you’ve had in a while, or maybe ever, and that’s unfamiliar. You don’t have to keep rocking the boat. You can just enjoy the ride, you know.”

For some reason, hearing it from Sadie didn’t feel like an attack, but something more like a validation. I was trying to ruin a good thing, just because it was a good thing. A memory from the past came shooting into my mind: the time that I watched my dad push his plate away after my mom had made his favorite dinner of steak and potatoes.

“You love steak and potatoes,” my mother had responded angrily.

“And that’s exactly my point,” he had shouted. “You always give me what you know I like. It’s boring. It’s suffocating.”

I remember thinking at that time, as a fourteen-year-old, “What an idiot. If a woman ever treats me that good, I’ll never let her go.”

And here I was.

I apologized to Sadie and admitted that she was right. I had been foolish. I had been scared. I wouldn’t make that mistake again. I didn’t call the therapist again, but I did start to think about how I might have been looking for complicated when simple and wonderful was right in front of me.

When it came time to renegotiate, we decided to keep seeing each other. Three months later, we did the same. And again and again, to this day.