My Sugar Daddy Lost His Fortune, and It Redefined Our Entire Relationship

We got the call when we were just landing in Fiji, ready for two blissful weeks of beaches, yoga, and meditation. The call was from my sugar daddy’s wife, soon-to-be ex-wife, and I begged him to just call back when we had reached the hotel. But, you know, it was a stressful time in their relationship, and he wasn’t going to be calm until he took the call. From what I could hear, his wife was somewhere between cackling and crying hysterically. I could just make out her saying his name, “...Howard…” over and over in different shades of desperation and anger.

Mind you, we hadn’t even passed customs. We hadn’t even got our bags. It was 2 am, after a 16-hour flight, and I was trying to shepherd us through the airport so that we could find our chauffeur and get to the hotel. But, just as I found our driver with a sign with his name on it, Howard stopped in his tracks. Just stopped right in the middle of families hugging and couples on honeymoons.

“It’s all over,” he said, almost under his breath as he hung up the phone.

He was in shock; I could see it immediately. And I knew the only thing to do was to get him to a place that was away from everyone so that he could talk and we could figure it out together. Once we got to the hotel, Howard threw down his bag, picked a pillow up off the bed, and threw it across the room (sweet, Howard, even when he’s furious, he’s never destructive.) Then he crumpled to the floor and started crying.

From what I could surmise, Howard’s wife had learned about our relationship and had already started the divorce filings while we were in flight.

At first, I selfishly thought, “Well, okay. At least he won’t have the burden of keeping secrets anymore, and we can start living more openly.” I knew that Howard had been extremely unhappy in his marriage for a long time. And his wife had certainly had her own string of affairs before I ever met him. So at first, it did feel like a potentially positive thing.

But then Howard went on to explain that he had married into his wife’s wealth and she had made him sign an airtight prenup before they got married.

The timing couldn’t have been worse. Howard had just made a huge investment in a new company that he was certain would make him independently wealthy. His idea was that once he was on his feet financially, he’d be able to divorce his wife and they could go their separate ways more or less amicably.

But now, with legal fees and his wife’s desire to end his business venture any way she could, Howard had to admit that this was checkmate. Over. He was about to hit some very hard times, very quickly.

It was the longest night of our lives. I didn’t know what to say or how to help Howard. We did plenty of breathing exercises, but there are some things that you just have to go through, you know? Howard’s body and mind were in the early stages of a whole new chapter of life, and there’s really nothing that anyone can do to make that easier.

By the morning, he was still a wreck, but he managed to sleep a couple of hours. He had already booked a flight back to New York but insisted that I stay for the next two weeks without him. This was crazy, of course. I told him that I had no desire to stay here by myself, especially considering the state he was in.

But he was pretty stern when he told me that he wasn’t doing this to be nice. For one thing, the trip was already paid for, and he would be livid if all that money he spent was going to be wasted. That was exactly what his wife had wanted by waiting to call him when he landed in Fiji.

There was a part two to his reasoning, though. And this one was harder to stomach. Howard said he needed some time alone to figure things out, and he would prefer if I weren’t with him while he did it. This was honestly scary to hear. I didn’t like it at all. And I told him as much. But he assured me that it was just something that he had to do. He wasn’t breaking up with me, he said. He just needed some time to be on his own. He wasn’t planning on ghosting. He just needed to not see me for a little while.

I did try to make the most out of my solo vacation. I journaled a lot, and a lot of the journal entries were actually letters to Howard, telling him about what I was up to and how much I wished he were here with me. I did yoga. I swam in the ocean, and I met other people on vacation.

Of course, I worried constantly about Howard, and I couldn’t wait to call him when I landed back in New York. He said that he wanted to meet up for a coffee a few days later, and I got a sinking feeling in my stomach, but I said, yes, of course.

When we met, I could see that Howard had in mind exactly what I hoped he didn’t. He wanted to break up.

“It’s not personal,” he told me, “I have feelings for you, and the last thing I want to do is stop seeing you. But I can’t give you the lifestyle I agreed to when we met. I can’t give you anything. I’m going to be spending a long, long time rebuilding. Maybe when I’m in a better position, I can reach out to you again, and we can see where we’re at.”

I know a lot of sugar babies who would take the out and never talk to someone like Howard again. And I do agree that you shouldn’t date a man for his potential, especially when you’re sugar dating. This situation was different, though. I genuinely had feelings for Howard. It had always pained me to see him so unhappy in his marriage, and I had always felt really bad about being the other woman in his life.

I told him flat-out, “No.” I wasn’t going to let him break up with me like that. For sure, we’d have to rearrange some things. I would continue sugaring, so he’d have to be okay with that. And I didn’t want him to go further into debt just to take me out to dinner, so I told him we’d switch to free or low-cost dates. You know, coffee walks in the park. Trips to the museum on discount days. Yeah, he’d have to be more romantic and thoughtful, maybe, but this was how the relationship would have to change if we wanted to keep seeing each other.

The good news is, sometimes seeing someone’s potential isn’t just wishful thinking. Yes, Howard took huge losses with the divorce. He moved into a sad bachelor pad, and he sold off all the assets that he was granted in the settlement just to pay off debts. He stopped dying his hair (I mean, that was a relief, to be honest) and started dressing more casually.

But, it turns out I wasn’t the only person who saw his potential because the guys he had gone into business with when his life went sideways didn’t want to kick him to the curb. They actually did everything they possibly could to keep him on. And their belief in him paid dividends. Within three years, Howard had the level of financial stability that he had always wanted. It wasn’t what he had before. But it was enough for him to live comfortably and treat me to pretty luxurious dates every once in a while.

We were even able to plan that trip to Fiji again. Okay, not in as fancy a hotel as before. But this time, there was no drama. There was no crying. Actually, that’s not totally true. It was during this trip that I brought out my journal from those two weeks alone and read it to Howard. I’m pretty sure he teared up when I read the part that goes:

“I’m looking out over the most beautiful sunset I’ve ever seen. It doesn’t even look real. I’m drinking a coconut water with a lime garnish, and I can hear birds and waves crashing. It all feels very luxurious. But it’s also hollow. I would easily give all of this up for something more low-key with you. I hope you feel the same way.”

And now he knows that I’ll be with him for the highs and the lows. Sometimes, you gotta take a chance on a guy like Howard.