From Sugar Arrangement to Love: My Journey with My Sugar Baby

I remember the moment very clearly, the same way that you might look at your partner and realize for the first time, “I think I’m falling in love with them.”

It was not at a particularly romantic moment. In fact, it was decidedly not romantic. I thought we were breaking up. And I had been a real jerk about it.

But first, some backstory. I had been in a terrible mood all day at work, for a variety of reasons that don’t matter. But I remember that I was not feeling warm and fuzzy about seeing these people, my colleagues, again after work for the firm-wide mixer, no matter how much it might boost my career. And in fact, I had been strongly considering ditching it altogether and taking my sugar baby out for dinner and a movie instead. I was thinking she’d probably actually prefer that instead of being my date, even though she was always such a good sport about being my plus one.

Then, I got the text from her that said, “Can you meet up for coffee before the mixer? There’s something that I’d like to discuss.”

Great. I thought, for sure, she was going to break things off. Maybe she was done with this whole arrangement concept. Maybe I had said something stupid. Maybe she had met someone better and richer. I (barely) kept myself from spiraling so that I could get through the day and then meet up with her at our favorite coffee place.

She looked, as always, beautiful. Her black hair was pulled back in a neat bun, she had gone with a natural makeup look and professional (if maybe a little too tightly-fitting) pencil skirt and blazer. And she was chewing on the inside of her bottom lip and staring at the coffees that she had already ordered for us. That little vertical line between her eyebrows that she hated so much was present and accounted for, as it usually was when she was nervous.

For the first time since I had read her text, all of those self-pitying doubts and abandonment fears fell to the wayside, and I could see clearly that the real tragedy here would be losing her.

We had spent five months together. And for the most part, I had been able to keep from getting attached. She never stayed over. I didn’t ask about her personal life. I only knew that she had a dog because sometimes she would come over with one or two wiry stray hairs that had managed to escape her meticulous lint rolling.

And then, one day, about a month before this gut-wrenching moment, I had slipped up. I had an emotional response to her ice cream order. Yes, I know. It seems too trivial to be life-changing. But there was something about it that strummed at my heartstrings just a little bit. I mean, who orders plain vanilla ice cream? That’s borderline psychotic! It was just, I don’t know, too endearing not to create an emotional stir within me. Listen, I may be a defense attorney, but that doesn’t mean I don’t have a soft side.

Well, as they say, it was a slippery slope from there. I started to want to know more about her, about her favorite films, and whether she listened to podcasts. I asked her what kind of hobbies she had, what her friends were like. She told me some things. She was vague about others.

Maybe, I was thinking as I sat down across from her after planting a quick kiss on her cheek, she had realized that I was developing feelings for her. Maybe that’s what this was about.

I can’t logically explain this next part, but for some self-sabotaging reason, I decided to just get ahead of this thing. End it. Rip the band-aid off.

“Listen,” I told her. “I think I know what you’re going to say, and you’re right. I’ve let myself get a little bit more attached than I thought. And we both know how these things go when one person starts to develop feelings; it all goes to hell. So, let’s just do ourselves the favor of ending this quickly.”

As horrified as I am to admit it, I pulled out my phone and deleted her number right there in front of her. Her jaw literally dropped open. And then, I left enough money on the table for probably ten coffees, and I left.

The panic was threatening to hit me as soon as the door shut behind me on the way out, and I realized there was no way that I could face going home after that. So, I did the only thing I knew to do: I went to that stupid mixer. There’s always plenty of alcohol at those things, so I started taking long gulps of whiskey anytime anyone asked me where my sugar baby was. Of course, they called her by her name, but I had always introduced her as my girlfriend. I told everyone she was busy that night, which puzzled one of my colleagues, who said, “Wait, isn’t that her over there?”

I tried not to spin around dramatically, although the alcohol probably made that impossible. And there she was. She was smiling as she smoozed her way through the crowd towards me, stopping to say hello to my colleagues, asking after absent wives. When she finally got to me, though, I could sense that she was raging underneath the facade.

“Can I speak to you outside for a moment?” she demanded politely.

We went up to the roof, which in hindsight was a bit risky given how angry I knew she was.

But as soon as the door to the stairwell closed behind us, she started crying.

“I asked you to coffee so that I could tell you that I broke things off with my other sugar partners and deleted my dating apps. I wanted to be exclusive with you. I also have feelings for you. But what the hell was that? Like, is that how it’s going to be the next time you freak out? You’re just going to try deleting me out of your life?”

I immediately started blubbering about how sorry I was, what an idiot I had been. That I didn’t want to be with anyone else and had acted out of sheer panic that I was losing her. The sun set in front of us, and we were still talking about what this relationship would even look like and what it would mean for me to rebuild trust between us. And by the time we came back down to the mixer, everyone was already gone.

I was a bit annoyed that I wasn’t able to have her on my arm as my real girlfriend for the first time. But there will be many more mixers in the future.