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Skip ! In the past, we've interviewed several sugar babies both men and women as well as sugar mammas to chat about their experiences with sites like Seeking Arrangement, where men and women get paid to date, and find people willing to pay them. Each interviewee had varying experiences with sugar dating websites, with some sugar babies ready to marry their partnersand a sugar mama considering giving her dates a "gift fund.
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Tell me about yourself. I travel a lot, but I'm based in New York. I was divorced about 3. I jump out of planes, you know? Why did you feel like you couldn't go back into conventional dating? 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. So how did you end up on Seeking Arrangement? I started using the site because I thought it was the only way to meet women who have not been tainted by life. What do you mean, 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. It was so incredibly refreshing. It was just amazing to me. I thought, maybe I should start to pursue younger women. So I found Seeking Arrangement.
Who did you end up meeting on there? There were three women I met on the site.
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The first woman was the "upfront woman. 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. 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. What happened with that relationship?
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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. So we decided to remain friends. And the third woman? 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.
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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.
What do you mean a real relationship? Did you want monogamy? So I told her, okay, well you have to be upfront with me, not just honest. That should be the best part about a site like Seeking Arrangement is you shouldn't have to lie. 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. How much did you spend supporting her? I bought her a lot of jewellery. 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.
I know. It was sort of like, hey dude, what are you doing? And you haven't been back on the site since? 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.
Well that's interesting, because isn't that how you were describing older men and women who are "tainted by life" ly? 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 meI just squash it a little bit. Has that experience changed whether you would date women of a certain age? 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. I feel like an older woman is more likely to be communicative and say, "I don't want to do this anymore. The girl I met on Seeking Arrangement used to say that all the time. Just because you have the money you have the power. Well, so who are you dating now? And she ended up sitting and having a glass of wine with me.
With a lot of discussion about moneyed, older men abusing their power, has it changed the way you view your relationships? 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?
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 behaviour.
Given the fact that you make more money than your girlfriend, do you also support her financially? 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. So how would you differentiate what you're doing now from sugar dating?
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. Were you ever concerned about people only dating you for money? I was always concerned about that, and there's no real way to know. Unless you stop helping them financially, I guess. 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. Of course they'd say yes, but there was no real way to understand if it was real.