The Sugar Arrangement That Turned Into a Long-Distance Relationship

When I first met my sugar daddy, we had the idea that it would be a short-term, casual situation. I was back in the city where I grew up for just a few months before I would be starting a new job on the other side of the country. And I didn’t want to work at a coffee shop or sit around on my couch all day, so I decided to spend my time off sugaring.

And to be honest, I had a lot of free time. So I was doing a lot of sugaring. Sometimes I was someone’s girlfriend for the weekend while their family was in town. Sometimes I was a plus one to a fancy dinner party. Sometimes, I just met up with a sugar daddy for one single date before realizing we weren’t compatible (but still very much enjoying the high-end sushi and dessert).

But throughout my time home, one of my most consistent sugar daddies was Riley. My dates with Riley were so easy! He’s such a Type A planner and a thoughtful person. He knew that we didn’t have that much time to spend together, so he made every date unique and fun, and he gave me sweet gifts every time we saw each other.

Towards the end of our time together, it was becoming obvious that we were going to miss each other. Or, at least, I was realizing that I was going to miss him. I mean, I had a feeling that Riley was probably this dreamy with all of his sugar babies and that he would easily find someone to replace me once I was gone.

So, it took me by surprise when, on our second-to-last date, he started crying. Yep. A pushing-50-year-old man in a fancy dress-code restaurant on his first whiskey on the rocks of the night. Broke down in tears right in front of everyone.

I picked up my chair and set it down right next to him so that I could put my arms around him.

“What in the world is this?” I asked gently.

“I’ve never met anyone like you,” he said. “And once you’re gone, I’m just going to go back to my normal life, which isn’t bad. But, it’s just been better since you’ve been in it.”

I was almost speechless. Almost.

“Okay, well, first things first. We’ve still got two weeks together. So, let’s make sure we’re enjoying the time we’ve got left instead of wasting it on thinking about the future. Next, I’m not sure what you think is going to happen when I move, but I’m not going to be living in a bunker with no contact with the outside world. We can call and talk anytime you want to. I want that too, I’m not just saying that.”

We enjoyed the rest of our evening as usual, but there was a part of me that was eager to get home and think things over for real.

I realized that this may have been developing into more of an emotional connection than I had anticipated. And seeing Riley break down, when he had never so much as teared up at a heart-wrenching movie, I knew that he was feeling the same way.

But, did I really want to start a long-distance romantic relationship right now? I would be starting a new job in a new city. I would need to focus on meeting friends, and honestly, I had been planning on sugaring on the side in order to have a little bit of extra spending money. So, I wasn’t sure that I would have extra time for a long-distance relationship.

I spent quite a long time that night journaling about what I was going to do. And mind you, Riley hadn’t actually said that he wanted a long-distance relationship. I was worried that he was going to try to convince me to stay, which absolutely wasn’t possible. It helped to put all of it out on paper. I also called a friend of mine who married her husband after being in a long-distance relationship for two years. By the time we finished our call, I had a feeling that I would know what to do in the morning.

It’s true. When I woke up in the morning, I had this lightness in my chest, which was a weird mix of resolution and anxiety. I knew that I had to call Riley, and when I did, he said, “Okay, I hope this doesn’t scare you off, but I’m looking up flights to come visit you next month. I don’t want this to be over, even if that means I only get to see you once a month.”

“Make it every two weeks, and you’ve got a deal.”

And, that’s how it started: our year and a half of long-distance romance.

For sure, the adjustment wasn’t always easy. We had to have a conversation about the fact that what he had set aside every month for allowance was now going to go to flights. So, effectively, we were not only starting a long-distance relationship but also ending our sugar relationship. And we had to talk about what that would mean. We agreed that if we were going to do this for real, I wouldn’t want to see other sugar daddies anymore, and that we would become a romantic couple. So, you know, talking to each other every day, video calls a couple times a week, gifts in the mail, all of that.

Seeing each other every two weeks (taking turns going back and forth) was absolutely the key, but it still was tough. I was trying to use my weekends to make friends and find hobbies, but that's not so easy to do when you’re unavailable two weekends a month.

And, of course, there were issues with the difference in time zones and scheduling, and just plain missing each other. At one point, we kind of ran out of things to say.

Something that helped was that I actually started to follow long-distance relationship content on social media. I got ideas about how to keep the flame alive from afar and games that we could play to stay connected. I got more creative about my care packages to him and planning dates that weren’t just us enjoying our alone time after two weeks apart.

At the end of a year and a half, I think both of us had kind of reached the end of our rope. I didn’t want to keep doing this forever. I had already decided that I would rather end things between us than keep going the way we were going. And, as much as it pained me, I was thinking about how I would tell him.

Before I could, Riley called me to tell me he had booked an impromptu trip to come see me the next week. I thought maybe he was planning the same thing I was, and I didn’t want to wait until our next visit.

But when I picked him up from the airport, he told me that he had somewhere that he wanted to take me instead of going home. He looked excited and happier than he had in quite some time.

We pulled up to a fairly fancy neighborhood, and he pulled up to a beautiful house with a for sale sign out front covered up with a “sold” sticker.

I felt my heart start to pound, but didn’t want to come to any conclusions just yet.

Riley reached into his pocket and pulled out a pair of keys. And then he grabbed my hand.

“You don’t have to move in with me,” he cautioned. “Unless you want to. I mean, that would be wonderful. But I just couldn’t do the long distance anymore. I told my job that they could have me in the office one week out of the month, and the rest of the time, I’ll be remote, here. The hours are going to be an adjustment, but I’ll adjust anyway I need to to have you in my life.”

Now I was the one crying. I moved in immediately, although I kept my apartment for a few months, just in case.

And that’s how we went from short-term hookup to long-distance relationship to moving in together! Like all love stories, it had some ups and downs and moments of frustration and desperation. But I couldn’t imagine a better ending.