One night, Rebecca, a New Yorker in her late 20s, opened Netflix and decided to watch This Is Life With Lisa Ling alongside her same-aged boyfriend.
The docuseries, which focuses on different subjects, has one episode specifically dedicated to the topic of Sugar Babies, and the website Seeking Arrangement. On the site, Sugar Babies (typically women who are paid for dates) meet their Sugar Daddies (men who pay women for dates). Sometimes, women are Sugar Mommas and men are Sugar Babies. This applies to same-sex arrangements as well.
A few months later, unrelated to the docuseries episode, Rebecca and her beau parted ways.
“One of the participants [in the episode] was a woman about my age,” says Rebecca. “She was seeing a much older man, and they ended up having a multiple year ‘arrangement’ as the site calls it.”
The site, which has gained a fair share of backlash and criticism, states on the homepage “Relationships on Your Terms. Where beautiful, successful people fuel mutually beneficial relationships.”
“Most assume these arrangements must include exchanging sexual favors, which is illegal, and the Seeking Arrangement website talks a lot about this,” says Rebecca, “However, [in the documentary], this pair truly built a special friendship. In this case, there were no sexual favors exchanged: the arrangement was really about spending quality time together and enjoying each others' company.”
Rebecca had what she calls an “ah-ha” moment while watching, and thought, "This could be a helpful form of therapy for some people." From her perspective, individuals in need included lonely, aging men with wealth, who enjoy taking care of beautiful women. In theory, these would be gentlemen who preferred to spend time laughing and feeling upbeat through their dates' youthful energy.
Simultaneously, she realized, there are young women in need of financial assistance that are willing to be paid for their time. “I see this as a win-win,” says Rebecca.
Through more independent research, she decided to sign up.
On the Seeking Arrangement app, both babies and daddies create profiles, just as singles do on other dating sites, services and apps. The twist: Sugar Daddies indicate how much money they are willing to pay for an arrangement. They’re also not required to post a photo of themselves, while the Sugar Babies are. Sugar Babies can include their price point as well.
“You are able to ‘like’ profiles, and can message each other within a messaging platform,” says Rebecca. “This is how most arrangements start. I spent a lot of time messaging before I met anyone in person, as a safety measure and to just feel more comfortable. It's also good to nail down the terms of the arrangement prior,” says Rebecca, who felt in control and maintained the power throughout. “I set the terms on offering no sexual favors of any kind, how much I expected to be paid monthly, and many dates were included.” Rebecca notes, you can also set terms for travel (such as vacation or how you’re getting to and from dates/meet ups), and when they can text you.
Before connecting with men on the app, Rebecca thought twice about using her actual name. “I did use a false identity, and I think most [people] do. Obviously, those paying – the Sugar Daddies – are much more private. Some are really well known men. Some are married,” said Rebecca, who only revealed her actual identity after meeting her match three times in person and agreeing on an arrangement.
As an attractive, fit, and fun female, there was no shortage of men looking to meet up with Rebecca and connect. She received roughly six to ten messages per day but only chatted with half of those. There were a range of personalities. Some guys were incredibly wealthy (they can choose to include income figures on the site), while others traveled a lot for work and wanted to share a meal with when they popped into NYC.
The conversations started as other dating app connections do: with witty quips or a comment about a photo or profile detail. “I was pleasantly surprised. I thought it would be creepier, deviant, and scary, even. But it wasn't at all. I was the one with the power, the one in control, and the one setting the terms.”
While most of Rebecca’s suitors were well-mannered gentleman, one made it clear he was looking for sexual attention. She ended the chat immediately.
“I was looking for a smart, unmarried, older business man that I would actually enjoy spending time with,” she says of her search. “Beyond wanting to pay off my grad school loans, I was looking to engage on an intellectual level and create a sort of mentorship-type relationship out of it."
Rebecca decided to meet up with one of her matches. It was her first in-person meeting, and she agreed to an arrangement on the spot.
“He was super sweet. The arrangement was for $6,000 per month, seeing each other about once per week – but he traveled for work a lot, so sometimes less. He understood I was working full time and couldn't drop everything to travel with him,” says Rebecca. “Our dates were very date-like, as with any other relationship. We went to dinners, walked in the parks, and watched the political debate one night. We talked about normal things: background, family, work life, etc.”
Actively looking for a romantic life partner, Rebecca was seeing other people and felt odd at first. “In the beginning it felt a little weird, but after a date or two, I truly saw it as business.”
After two months of seeing each other, Rebecca decided to end things. “He indicated we would like to include a sexual component to the arrangement,” she says. “This was not acceptable to me, so we parted ways. In the two months, I made $12,000.”
Even though the relationship terminated, it was amicable. “While he was a bit frustrated that I wasn't willing to add a sexual component, he was a gentleman and understood.”
Rebecca hasn’t engaged in an arrangement since, but she’d be open to it again.
“I would recommend it to very strong and independent women who don't necessarily need the money,” she says. “I would not advise this being your full-time job; many [women] on the site do this.”
Her best advice for Sugar Baby participation?
“Have your own life, have a great job, and have fun with this to pay the extra bills or treat yourself to things you couldn't afford otherwise.”
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