I Dated a Rich, Older Man, but his Money Stopped Feeling like Care

I admit I like being taken care of. 

A part of me was curious. I had, for some time, been harboring this fantasy: I’d go on a date with an older, rich man. I’d have an excuse to get dressed up, to be alluring. To wear earrings, heels. To feel like I was a delicious treat for this charming man to lavish with expensive gifts. 

I don’t even know where the fantasy came from except that I grew up with money. When I was a child, I didn’t go to McDonalds, I went to Baccas, the little French bistro one town over. I traveled to Europe when I was 14, went sailing in the Carribean to celebrate my high-school graduation. In choosing to follow my dream of being a writer, I let that all go. Perhaps I wanted a “Daddy” to give me that life again. How different it would be from the broke, split-the-pizza artists I was used to dating. 

I wasn’t quite curious enough — or perhaps brave enough — to go on sugaring sites, couldn’t quite bring myself to straight up exchange sex for money. Instead, I replied to this man’s message on OkCupid, my fantasy illuminating his faceless photo — a body in a suit — with a halo of light. Looking back now, going straight to a sugaring site would have made things much simpler. 

The truth is, my fantasy didn’t extend past a date or two. 

I didn’t think as far as whether I’d go home with the man, if we’d have sex, or if we’d go out again until we were, quite simply, in a relationship. 

Our relationship developed slowly. Outside of my fantasy, I was intimidated by his age, money, and power, so I told him I just wanted friendship, and for a while, that’s what we were. I brought him to arts events and he brought me to dinner. He had money, but I had spirit, I knew where to go for a good time. 

It took me a while to warm up to the idea of dating him, but a couple of months in, I felt a shift. Getting ready to go out and meet him at the white-tablecloth Vietnamese restaurant, I found myself putting on a low-cut shirt, heels, and some silver earrings. I realized I was getting dressed for a date. 

I certainly didn’t imagine I’d end up spending eight months with him, making plans to move abroad and leaving my life as I knew it to be with him. I hadn’t expected to fall in love. 

The longer we stayed together, the more the fantasy wore off and reality set in. 

This was not just a fun night out — we were in a relationship. The exciting life we’d begun sharing of flitting from show to show, restaurant to restaurant, each night ending up at his place for sex and sleep, only to do it again the next weekend, screeched to a halt when the pandemic hit. It left us with the barebones of what was just us. 

The rest of our relationship was limited to his apartment where I learned of his eccentricities and he learned of mine. He wasn’t just “some rich guy” — he needed his apartment spotless, my voice steady and unemotional, and he didn’t like when I said certain words. I wasn’t just “some sexy young woman”; I had an emotional streak that was becoming harder and harder to control. 

I began to feel uncomfortable with our income discrepancy and with him paying for every meal. I chipped in when I could, but as a writer who worked odd jobs to make ends meet, the restaurants we went to were well above my budget. Then there was the fact that if we followed through with our plans of moving abroad together, we’d be doing it on his dime. 

It’s one thing to let someone treat you once or twice, it’s another when that “treating” becomes a constant feature of a full relationship.

I began wondering how much money was impacting our relationship. I was attracted to him —  I knew that —  but I started getting caught in my head and questioning the sincerity of my feelings. I liked him — I loved him — and I wanted to be with him, to have sex with him. It wasn’t because of his money, right? 

We talked about our income discrepancy multiple times. 

Because we talked openly about BDSM and kink, feeling our way into our own personal version of what that was, it wasn’t strange when he suggested:

“Maybe sometime when we go out, I’ll pay in cash. You’ll have to sit there and squirm.”

I imagined it — I’d have to watch him take out a wad of bills. He’d be entirely focused on counting them. He’d ignore me. 

Indeed, the thought alone made me squirm. I felt all the uncomfortable feelings of submission that I was becoming familiar with through playing with bondage and the D/s dynamic we engaged with in the bedroom.

There was self-doubt, a desire to flee, and helplessness. But I was trapped — not by rope, but by social etiquette and, quite simply, commitment to our relationship. I couldn’t just leave because of a single moment of discomfort. 

We never got the chance to play with that fantasy. The pandemic summer of outdoor dining became a pandemic winter of take-out food. 

When playing with submission in bed, I learned to enjoy the feeling of being trapped in discomfort. When I couldn’t escape the discomfort, I would get aroused. 

But I only felt safe to go to that place because I knew that at the end, he’d untie the rope and we’d be equals again. 

I couldn’t find a way to untie the rope in real life. 

His money, career, gender, and age all put him in a position of power and privilege. In my vague fantasy of being with a man like this, I didn’t imagine how uncomfortable it could become to feel powerless to these facts, never escaping them. 

That’s why I realize now, had I wanted to play with money as power, a sugaring relationship would have been much clearer; expectations and boundaries would have been clearly spelled out at the beginning.  

Being with him, I stopped feeling “taken care of”. Maybe money could be a form of care, but I needed more than that. His small requests about how I should behave began filling me with resentment but I continued complying because we were at his place and eating the food he paid for. 

This lack of care I felt at the end was what led me to lose my cool. 

I could no longer contain my frustration and keep following his rules, and one night I lost my temper. He ended our nearly year-long relationship on the spot. 

The last I heard, he was dating a 24-year-old woman: 10 years younger than me and several years younger than half his age. We attempted to continue a friendship for a while, and from what he told me during one of our phone conversations, she’s comfortable with their age, money, and power differences. 

Perhaps a dynamic like this can work. For me though, I felt I was always in ropes, and I didn’t seem to have the ability to untie them.