When I met my sugar baby, Masie, 8 years ago, she was a recent college grad, living care-free and wild in New York. She was far from ready to settle down and just wanted a wealthy older gentleman to treat her to all the nice parts of the city and maybe help her pay for the occasional mouse exterminator or locksmith when she drunkenly locked herself out of her apartment.

And, make no mistake. I was happy to take on that role for her. I found her to be so charming and sweet, and I loved her tendency to get radically political after just two glasses of chardonnay. In fact, I learned early on that I couldn’t invite her to my work mixers unless I was ready to haul her away from a verbal altercation with one or more of my older conservative colleagues. Despite her insults, everyone in my life loved “Crazy Masie.” And I may not have loved her fully, but I certainly had love for her. Even when she called me at 2 am, asking me to come get her from Long Island and bring her back to her place in East Harlem. Like I said, she was living the wild New York life, one that I missed dearly and had long since put to bed for myself.

Anyway, we spent a couple of happy years like this. She jumped around from odd job to odd job in digital marketing, which gave her just enough of an income to scrape by (along with my allowance, of course) and plenty of free time to enjoy herself. She wasn’t overly ambitious. She never expressed long-term goals like owning a home or starting a family. For the moment, she was content.

For some reason, this kind of bothered me after a while. I think because when I was her age, I was under a lot of pressure to start my career, move up the ladder, do the traditional American dream thing. It was equal parts child of immigrant mentality, personal ambition, and simply not knowing that there was any other way than putting in 60 hours a week.

But any time that I brought it up to Masie that maybe she should start building a long-term plan, she wouldn’t have any of it.

“Just because you allowed yourself to be put into a box doesn’t mean that you can put me in one, too,” she would say to me. And that would shut me up, sure. But not before I reminded her that my box was the reason she was able to live so carefree and young all the time. Then, I would leave dramatically and give her a couple of days of silence (never missing an allowance, of course, I’m not a monster.) And inevitably, she would call me at 2 am and apologize and ask for a ride. And inevitably, I would. As I said before, I had a lot of love for that girl.

Things changed for Masie when she got hit by a car while she was riding her bike. She didn’t have any life-threatening injuries; she walked away with a broken rib and sprained ankle. But I could tell from the minute I arrived at the hospital as her emergency contact, that she was shaken emotionally.

We all have that horrible, eye-opening moment, don’t we? When life gets real, and we realize that we’re not immortal. I stayed with Masie all day and night and then checked in on her every day after work that week, bringing her food, sending her laundry to the cleaners. I even cleaned the litter box, and I hate cats.

Really, I was worried about Masie, who seemed to have lost her crazy aura. She was subdued and moody. Her recovery was slow because she wasn’t doing the exercises that her PT recommended. I kept teasing her that if she didn’t do her recovery workouts, she would lose her ability to dance on tabletops all night. She would smile, but it honestly didn’t seem like she wanted to go back to that life.

Finally, I got tired of waiting for her to bounce back. I asked her outright what was going on.

“I don’t want to hurt your feelings,” she told me. My stomach sank, but I encouraged her to go on.

“It’s just that,” she said shyly, “I am in this kind of helpless state. I’m really having a hard time with it. And you’ve been great, you really have. But I want the person who takes care of me to be, you know, my person. I didn’t want it before, or maybe I did but I thought it would be way in the future. But now I’m sure. I want to find someone to share my life with. I want someone who is in love with me.”

“I care about you, Masie,” I told her.

“I know you do,” she put her hand out for mine. “But you don’t love me. And I care about you. But I don’t love you. And that’s okay. I didn’t have any delusions about what this could be long-term. I’m just thinking that maybe I need a break so that I can focus on—ugh, you’re going to love to hear me say this—getting my life together. Maybe it’s finally time to find my box.”

I told Masie that there was no way I was going to leave her without help while she was still in recovery, but I offered to hire a caregiver for the time being, someone to help her get back on her feet. She was open to that, but told me that she didn’t want my allowance anymore. And that once she no longer needed the caregiver, she wanted us to take a formal hiatus.

I was pretty down about this, but I didn’t show it in front of Masie, or at least I tried not to. And I didn’t mention anything to my friends; they would have laughed right in my face at the idea of me crying over the end of a sugar relationship. I simply went to work and exercised, and went to happy hours after work. All the normal things.

A little over half a year later, I got a call from Masie. Not at 2 am but 2 pm.

“What, are you in a different time zone?” I teased, “It’s not the middle of the night here.”

She laughed and told me, “No, and I can’t believe that you’re not congratulating me on how strong I had to be to not drunk call you for the last 7 months. A true feat, on my end.”

Our old banter sent a pang of feeling through me.

“Listen,” she said. “This might be weird. I hope it’s not because I really, really want you to come. But I’m having a dinner party. I’m introducing my new boyfriend to some important people in my life. And I totally understand if you don’t want to come.” “I’ll bring the chardonnay,” I told her.

“Please do, but actually…I’m not drinking anymore.”

There was a pause as my mind went to a million places, or more specifically, to calculations. 7 months.

“No, no!” Masie interrupted my thoughts. “I’m not pregnant! I’m just not drinking anymore. I told you, I’m getting my life together. It’s all good things happening.”

Leading up to the dinner party, I found myself getting more and more nervous. What was Crazy Masie’s idea of inviting her former sugar daddy to meet her current boyfriend? Was I going to be some kind of prop to make him jealous? Was I there to add some kind of odd flair to the guest list?

But I should have known Masie better than that. When I arrived, she brought me straight over to her new guy and introduced me by saying, “This is who I’ve been telling you so much about. Without Clark, I would probably still be in my party phase. But, he really turned me around.”

Masie’s guy was warm and open to me, which was surprising. Masie would tell me later that he also had had a sugar momma early in his 20s, so he understood. In fact, he never batted an eye when Masie and I continued to have the occasional lunch date together, platonically, of course. And while she no longer drank wine, I could even still sometimes coax her into an inappropriately heated political argument in the middle of the day at an upscale restaurant. Good old Masie. I was so glad to have her back in my life again.

I’m not going to say that the transition from a sugar relationship to friendship wasn’t without its thorns. A few years later, when I received her wedding invitation, I left it unopened on the side table for weeks before I felt ready to tear it open and face the music. When I finally did open it, Masie had included a handwritten note saying that she had finally found her box (with a very beautiful ring inside) and was paying for the wedding with her own money from a career that she had started after I had pushed her to get serious.

She said she hoped I could attend. And, I did.