I’m 50, A CEO, & A Former Sugar Daddy — Here’s What I Want You To Know

I’m a founder and CEO of a global software company. My net worth is north of $50 million. I travel a lot, but I'm based in New York. I was divorced about 3.5 years ago, and when it came time to get back into the game, I realized I couldn't go back into conventional dating. I’m 50 years old but I probably look 38. I’m incredibly fit, I work out all the time, and I have the mentality of someone in their 20s because I just love to have fun. I jump out of planes, you know? I’m just one of those guys.

My schedule just prohibited it. When I dated conventionally, it always followed the same pattern: Meet a girl, get to know them, they like the vibe. Then I start my crazy travel schedule and there's an awful lot of stress and texting. When are you coming back? Where are you?

So I thought okay, what if I financially support someone and when I'm here, I have the company of someone I enjoy. It seemed like the perfect solution.

I started using the site because I thought it was the only way to meet women who have not been tainted by life.

I just found that as women and men age, they get more tainted by their experiences. They create within themselves a negative bias as a standard operating procedure. I went on many dates with women in their 40s, and what I found consistent between all of them was they were immediately looking to find out how I was going to hurt them, even from date one.

Then I happened to meet a friend’s sister for dinner, and the sister was 31 and we talked for 6 hours. It was so incredibly refreshing. It was just amazing to me. I thought, maybe I should start to pursue younger women. But then it became clear to me that conventional dating wasn’t going to work. I wasn't meeting younger women in the bars I went to, and when you go on a site like Bumble, you’re aren't going to find many women on there who are open to dating a 50-year-old guy. So I found Seeking Arrangement.

There were three women I met on the site. The first woman was the "upfront woman." I met her for a drink and she was very open about the fact that as long as there was some chemistry, she would meet with me and sleep with me for money. Unfortunately, that's not really who I am. I need more of an emotional connection with someone, even though it might sound weird in that environment.

The next woman was someone I would call a "girl next door." She probably shouldn't be on the website, and she wants an emotional connection, but she needs financial assistance. So I dated her for four to five months. After two months she said, I don't want money anymore, I just really enjoy getting to know you. It really told me she wasn't looking for a long-term monetary benefit, and that you can have a real chemistry-laden relationship with someone.

Over the next two months, the age difference was slammed in our face. I remember I went out to brunch with her and her friends, and someone was whispering, you know, Whose dad is that? It didn't really impact me, but I saw the look on her face. When we talked about it later, she said she wasn’t necessarily prepared for that. So we decided to remain friends.

The third woman I call the "mercenary," and she was the most dangerous person I think I ever met. She scared the shit out of me. She would say anything to make you think she loved you. She lied about not having a boyfriend, not living with him, got all the money, gifts, trips, and plane tickets, and when her boyfriend finally threw her out, she came crawling to me. So she ended up moving in with me for a while, and then I got set her up in an apartment. Once, I got really ill, and I told her what was going on, and I said, hey, look we need to have a real relationship, or this isn't going to work. And to this day, I haven't heard back.

I didn’t expect monogamy but I was asked for it. So I told her, okay, well you have to be upfront with me, not just honest. If you have feelings for someone else then just let me know and we’ll cut it. That should be the best part about a site like Seeking Arrangement is you shouldn't have to lie. Like, this is who I am. this is my situation, if you want to be with me under these conditions then we’ll be together.

But the thing was, I was exposing her to my entire world — I have kids who knew about her, my ex knew about her — and she wouldn't expose me to anyone. She was saying all the right things but her actions weren't matching what she was saying. So I told her, either you change or it's not going to work. And then, ghost.

I spent $200,000 while dating on the site, and about 90 percent of that was on the third woman. I bought her a lot of jewelry. I'd buy her a ring, she would lose the ring or say it got stolen, and I'd buy her another ring to replace the ring. Then her rent, it was $3,500, $3,600, plus a security deposit. I know. It was sort of like, hey dude, what are you doing?

I went back on the site and had one phone conversation with a woman, but that was it. That last relationship actually destroyed my ability to trust, and it was one of the factors that broke up the relationships that followed. I would go into relationships prior with, let’s assume she’s not crazy and she’s nice unless there's proof that something is wrong. After, I approached relationships with, it’s probably going to be a terrible relationship, she’s going to lie and deceive me.

Absolutely. It was a really difficult thing to deal with. I became what I didn't like about other people through that relationship. It really took an awful lot of time to be able to process through that, and I'm still working on it. When the urge comes up for me to say, I think you might be misleading me, I just squash it a little bit.

If I were single, I would definitely date women who are older. I was looking at older women as being tainted and having the view that life is not the greatest thing in the world. After processing everything I went through, now I realize they’re just not necessarily willing to put up with bullshit and they’re not going to sit there and think everything is rosy all the time. I feel like an older woman is more likely to be communicative and say, "I don't want to do this anymore." What I've come to realize is that sometimes younger women don't know how to do that, especially if they're in a relationship where they need financial support because of the fear of the unknown, like, Oh my god, what’s next.

The girl I met on Seeking Arrangement used to say that all the time. Just because you have the money you have the power. But I view the dynamic of sugar dating as a mutually powerful relationship unless the sugar baby is desperate for money, and when they’re desperate for money, that’s when it’s a power imbalance. But I don’t necessarily view sugar dating as the man has all the power, because it's just as easy for the women to walk away. Unless, of course, financially they can’t.

The girl I’m dating now, I was eating at a restaurant outside and she walked by, dropped her phone, it broke in a million pieces and I helped her pick it up. And she ended up sitting and having a glass of wine with me. She is younger than I am, but it’s interesting — her mother is much younger than her father, so she's used to the concept.

A little bit, to some degree. I had a conversation with my current girlfriend about the dynamic of power because I clearly make a lot more money than she does. And I asked, do you ever feel like I have more power in this relationship than you do? And she looked and me and said, Not more power, but you clearly can do things I can’t, and that may make me feel a little jealous.

I am much more concerned now about the perception from my girlfriend's friends as they potentially view me as more predatory. And I think I have changed my behavior. In New York, I’m more likely to stick to places I know, where people know me. The bartenders, owners, or servers, they don’t just see me as some old guy dating this young girl.

My current girlfriend does have a job but she doesn't have a job that can pay for the lifestyle she likes, so I do find myself supporting her financially almost as much.

It’s perception, maybe. I want chemistry to come before the financial for me. That's the difference. Whereas the other way around, it's, Give me money, and then I'll spend time with you. When there's no feeling behind it, no desire to be with someone because you have a semblance of attraction, you're just providing a service. I could just hire a hooker for an hour, it's the same thing. And it's not just about sex; if the only reason she’s spending time with me is because she’s getting paid, then it doesn’t matter if we're having sex or not, that’s not something I would undertake.

I was always concerned about that, and there's no real way to know. Unless you stop helping them financially, I guess. That’s the only way I could know. Right now, with my current girlfriend, it's a little different. It's not something where she gets a monthly check from me every month, I just help her out here and there when, you know, maybe she has to travel to see her mother and she can't cover her airfare until she gets paid two weeks later so I cover it.

But that was the whole problem with sugar dating sites. I couldn't believe anything I was told. Like if I asked, Hey, if I’m not helping you financially, would you still want to see me? Of course they'd say yes, but there was no real way to understand if it was real.

I don’t necessarily know that it’s fair, honestly. I think the dynamic of a website like Seeking Arrangement is, you have to assume that whoever you meet on that site is going to say whatever they can say to accomplish whatever goal they might have. And that goal is getting money. I mean, I came to that conclusion after that mercenary relationship. There was no way to get around the fact that without money, that relationships would never had happened.