The Sweetest Lesson: How My Sugar Baby Taught Me to See Life Differently

I will admit that I have been described as stubborn.

I don’t necessarily think of myself that way. I think when you grow up taking care of your younger siblings because your parents were absent, you get tough. And when you have to put yourself through college (and then grad school, and then business school), you get a little tougher. And when you take over a business with hundreds of staff that provides life-saving services for many thousands of people, well, you either reach your toughest version, or they replace you with someone tougher.

So, no, to me, it’s not stubbornness. It’s simply an ability to make decisions under pressure, to trust my instincts, and to not settle for anything less than what I know I deserve. If I go to a restaurant and the wine list is sub-par, I’m going somewhere else. If a dinner party at a colleague's house runs late, I’m leaving early. To me, that’s not stubborn, it’s discerning.

At least, that’s what I thought until I met Alison. On our first date, she asked me about my pet peeves. Of course, I told her that it bothered me when people called me stubborn. I expected that her response would be to ask me whether those people were right, and I would have to explain my high standards. It’s actually a conversation that I like to have on a first date with a sugar baby, so that she can get a good sense of what it’s like to date me. It kind of sets the tone.

But her response wasn’t what I expected. She said, “That’s surprising because I don’t take you as an insecure person.” I asked her to elaborate. Who had said anything about insecurity? She continued, “To me, very stubborn people are that way because they are afraid of change or they’re afraid of getting vulnerable. They make decisions that protect themselves or are familiar instead of being open to other opinions or admitting that someone else might know something more than they do. And, I don’t see you that way.”

It was more thoughtful than I expected. And to be honest, I was flattered that she didn’t see me that way. But to be very, very honest, her statement shook something loose in me, and I realized that I did tend to stick with what was familiar or under my control instead of allowing myself to trust someone else.

I thought about the many times that I shut down other people’s ideas at work, not because they were bad, but because they were risky, and if they didn’t pan out, I would take the fall. I never took time off work because I didn’t trust anyone to fill my shoes. I thought, also, about how I never climbed into the bouncy house with my daughter because I felt like the other parents would lose respect for me. Those instances, after that statement, felt more like cowardice than ever before.

I went out on a limb and asked her if I had done something tonight that could fall into this definition of stubbornness. And, I could tell that she didn’t want to hurt my feelings, but I insisted that I wouldn’t be offended. Finally, she said, “Well, I guess, maybe this restaurant choice? Like, it’s nice and all, but I know of a new place in the neighborhood that has better ratings for the same food. And, I was going to suggest it, but you seemed really set on this place.”

I decided that maybe I could be a little bit more open.

So, I ended up bringing it up again with Alison later on. She was very sweet about it and told me that she hadn’t meant to offend or upset me. But I suggested that maybe one of the things that we could incorporate into our sugar relationship was the chance for me to practice being less stubborn. I actually wanted her to call me out when she saw me being hard-headed, like with a little wink or squeeze on the hand.

What worked about it was that I never felt like Alison was judging me or trying to change me. But instead, she was giving me little reminders of moments in which I had a chance to choose different options: the stubborn way or the more flexible way. And I could choose which one I wanted in the moment.

There was one time when we were driving back to the city after a weekend trip away, and I wanted to take the most direct route to get home as quickly as possible. Alison suggested that we take the more scenic route and stop at a restaurant with an ocean view that she had always wanted to try. I was pretty adamant at first, and she jokingly said, “If you want to choose the option that gets you into your pajamas and on the couch watching TV alone, I support you.” How could I fight with that logic? What was I in such a rush to get home for?

We ended up taking the scenic route, and I got the satisfaction of taking her to a restaurant that she had always wanted to go to. Sure, the food was subpar, and we hit traffic coming back into the city. But she had a great point: the only thing that my stubbornness was going to get me was a few extra hours of being alone in front of the TV instead of across the table from a beautiful woman. What had I been thinking?