From the Magazine: Sugar Babies

Is it love or an arrangement? Here’s another take on dating in 2021

It was a Tuesday night, and Marina was getting ready for a second date with a former colleague of hers. Their first one was a dream—they went out for drinks and “everything was perfect.” She remembers that her legs were shaky under the table. He asked her out on a second date, and she was elated. He would pick her up at 6 p.m.

To prepare, she did her hair and nails and slipped into a dress. They would meet at the office to go out for dinner. She texted him to check in before she headed over, when he had bad news. He had to cancel. He would let her know when he could reschedule.

“When they tell you ‘I will let you know,’ when they are not rescheduling right away, OK, he’s not interested in going on another date,” Marina* explained. “I was pretty much already dressed up, I was getting ready, I was getting my nails done, my hair done, for what? Being ditched?”

Originally from Italy, Marina, 40, has lived in Miami for four years working as a teacher at a local college. She said she’s always been attracted to men who were 15 to 20 years older than her—the man who stood her up was 65—but her relationships always ended badly. One man she dated proposed to her in front of her parents, then she discovered he was already engaged to multiple women. She constantly felt used by her partners.

Then, she saw a documentary on television that mentioned a dating service called Seeking Arrangement—a sugar baby and sugar daddy dating site that touted “relationships on your terms.” Marina had never done online dating, but something about this site intrigued her. There tended to be older men who were wealthy and could treat her the way she wanted to be treated.

When she signed up for the dating service, she found that there were a lot of guys who caught her attention.

*Name has been changed for privacy

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The Sweet Life

For those outside of the sugar world, it seems like sex work. After all, isn’t a woman providing companionship for money? But according to Seeking Arrangement, this simply isn’t true.

“The biggest misconception is that this is commercial sex work adjacent, or that sugar babies are prostitutes or escorts, and that’s just not the case,” says spokesperson Kimberly De La Cruz. “We call it relationships on your terms, and that’s sort of the beauty about Seeking Arrangement and sugar dating in general.”

She explained that sugar relationships are meant to be just that—relationships. While there are certainly financial benefits for sugar babies, it should not be transactional. In fact, signs of transactional acts or pay-per-meet will get you banned.

Based in Las Vegas, Seeking Arrangement was founded in 2006 and now also has offices in Singapore and the Philippines. The dating service boasts more than 22 million members from around the world. On the site, sugar daddies and sugar mamas pay for different tiers of membership while sugar babies join for free. Members on the site are encouraged to be upfront about their expectations—are they looking for a platonic friend, weekend companion, or a longer-term relationship?

While the typical relationship meets the stereotype of sugaring—an older, wealthy man with a younger woman—the age gap is not as large as one might think. According to De La Cruz, on the dating site, the average man is 42 years old and the average woman is 24.

“Men who are older have had more time to get their success together and get their life built. They’re the ones who are able to be generous and stay chivalrous and take care of their partners,” she says. “The women on our site, at that age, a lot of them are looking for someone who can help them grow.”

In fact, Marina is just one of more than 49,000 teachers who are members on Seeking Arrangement. Nationally, Orlando has the second-highest number of teachers on the site, while Miami comes in third. While chatting with men on the site, she found Scott, a man in his 50s who was tall, handsome, smart; the conversation flowed. About a month into dating, he asked her “if there was anything he could do for her.”

She told him that even though she was working two contract teaching jobs and had more than enough money to pay for a condo, the bank wouldn’t approve her loan. She made an agreement with the seller of the house to pay 50 percent up front and then pay off the rest over two years. After finding out how much money she made teaching, Scott would unexpectedly stop by her home to give her an envelope with money. Over the next few months, he gave her $15,000 to go toward paying for her condo.

“They call it a sugar relationship, but this is normal in Europe, that it’s the man who pays for things for the woman. So I didn’t find it weird,” Marina says. “I find it weird here if I go on a date and the guy is expecting me to pay the half.”

The two continued to date—she would cheer him on at his dragon boat race competitions, she was his date at a Christmas party he hosted, they ran errands at Home Depot together, cooked together and traveled to Key West. They introduced each other to friends as boyfriend and girlfriend, and Scott even met her parents in Italy.

But, like many relationships, Scott and Marina fizzled out after about six months. Even though it didn’t work out, she said it was one of the best relationships she’s had.

“It was probably the only time that I ended a relationship with someone and I didn’t feel that kind of anger, sadness, feeling of being used,” she recalls. “He always treated me with respect.”

Spreading the Wealth

With her baby pink hair clipped back and thick, long lashes, Dash Preistly was sitting in front of her camera in Tallahassee to record a new video for her YouTube channel back in January 2020. She had already posted tutorials on applying henna eyebrows, but this time, it would be about something she’d been doing for nearly six years.

Being a sugar baby.

“People think getting a sugar daddy is an overnight process,” she says. “Sugar dating is just like dating somebody that you would date regularly; the only difference is you get paid for your time or you’re compensated for your companionship.”

A year later, it’s still the most popular upload on her channel, and she’s uploaded more sugar baby how-tos since then. But where she gets the most traction is on TikTok, where she has more than 100,000 followers. In the Group Meet app, she hosts a sugar baby “level up” group with more than 200 members.

It all started when Preistly was attending Florida State College at Jacksonville on a volleyball scholarship—as a student athlete, she didn’t have to worry about how she was going to pay her bills or rent. This was a good thing, as she and her teammates didn’t have time to work between school, practice and games. She had no idea about sugaring until a teammate told her about it. Curious, she looked up Seeking Arrangement and signed up.

She was in sugar relationships from 2014 to 2016, took a hiatus for the next year when she transferred to the more rural Tuskegee University in Alabama, and has been sugaring on and off since 2017. Then in 2020, she posted the YouTube video that started it all. Preistly created the “21 Day Sugar Baby Challenge” online course in August 2020, where each day her students are given lessons on building their profiles, taking photos, creating a wardrobe, and conversation prompts, as well as building self confidence, valuing their time and being in control of their intentions. By the end of 2020, she had about 350 students enrolled. Preistly also published the e-book Cyber Sugar Baby 101 for strictly online relationships and has a new one, How To Date Wealthy Men.

“What I really want someone to understand is the confidence you have to have in doing this, or you won’t be successful,” Preistly says. “Being pretty gets you through the door, but it doesn’t keep you in the building.”

Girl Power?

At its most basic, feminism is simply equality of the sexes. But this gets complicated in relationships, when we balance what it means to be a woman in 2021 with leftover traditions and dating rituals. For De La Cruz, sugaring is about as feminist as it gets.

“When people say it’s not empowering, I say, ‘what is not empowering about having absolute say in who you’re dating?’” De La Cruz asks. “If you want to date somebody who owns a house, what’s wrong with that? I think as people start to understand what our community is and what we’re trying to accomplish, it’s a matter of time before people realize this is the modern way to date.”

Looking at even the most modern relationship, there are rules and expectations of give and take, and whether we like it or not, we all probably have a subconscious standard for how successful or wealthy we want our partner to be. A woman who is climbing the ladder at her job and can pay her bills may want to have a partner with the same ambition. She may not be interested in a 22-year-old man who can barely afford to pay his rent. (Or, maybe she does?)

“Regardless of what we do, we are all exchanging something for something else—time for money, gifts for services, money for attention,” says sexologist Marla Renee Stewart, a sexpert for the Lovers adult wellness brand and retailer as well as a teacher at Clayton State University just south of Atlanta.

She emphasizes that as long as all parties are consenting, no matter the relationship type, it’s fine. Both parties should be benefiting from the relationship, including sugar babies and sugar daddies.

“When a person uses their agency that feels beneficial to them, that is a feminist move,” she continues. “If they expect something out of you that doesn’t fit, then it’s time to move on and out of the relationship. Understand that not all sugar relationships are long-lasting, so it’s best to understand that upfront and know that your relationship might be a few months or a few years.”

On the other hand, Jane Caputi, a professor of women, gender and sexuality studies at Florida Atlantic University, believes sugaring is not feminist. With her research focusing on popular culture and gender-based violence—namely violence against women by men—she argues it’s the product of an unequal society.

“Women are originally defined as property and made into a resource,” she says. “Women have had to make a deal—particularly with the threat of violence out there. You have to make a deal and have a man to protect you and your children, and agree to keep other men away from you. That’s been the original deal. It’s not new at all.”

While a woman does have control and benefits from wealth in a sugar relationship, Caputi notes that it stems from women not having equal opportunities for wealth and achievement. She is still relying on a man to pay for her schooling or start a business, and she’s using her sexuality and companionship to get it—and there are preferences for thinner, fair-skinned women—and these resources are only available to her for a short window of time.

It’s a “transaction based on someone’s unequal station,” Caputi says. “Basically, if you even look at the language of ‘daddy’ and ‘baby,’ you see a power dynamic that’s very much rooted in a patriarchal society. The sad comment is that this is what our society offers.”

Not Everyone’s Taste

For Marina, sugaring was not a means of paying for her bills, but a way of maintaining a relationship and a lifestyle she wanted. Working two teaching jobs in higher education, she never had a problem paying for things.

“I think the main misconception is that the woman is lazy,” she says, sharing that she can work 70 hours a week between time in the classroom and the office. “I’m not lazy.”

Stewart explains that the desperate woman is a stereotype of the sugar world, but quite simply, some women are just good at it. While all relationships have benefits, sugar relations “are just a bit more transparent about what those benefits are.”

But as empowering as those in the sugar lifestyle claim for it to be, Preistly has written in her books and teaches her prospective sugar babies that it’s not for everyone. In fact, the stereotype of the woman doing it out of desperation is the worst candidate to be a sugar baby.

“I do think there’s also many people who are in desperate situations. I’ve gotten crazy emails and DMs on Instagram, ‘Oh, I’m so broke, I need to feed my kids,’ and people don’t understand that’s not why you try to resort to being a sugar baby,” she explains. “Part of being a sugar baby is having your ish together, and obviously you don’t.”

In fact, even though Preistly had success as a sugar baby in college, she recommends it for women who are more established than that. And as a sugar baby, Preistly has been strict about her boundaries. She said she has never had sex with a sugar daddy, and she turned down a man who wanted her to move across the country to be his sugar baby and assistant. Even though the money was good, the age difference was too great for her.

“I always teach girls how to really be in control within a relationship, and I know that the men that I was talking to were more focused on companionship,” she says.

As for Marina, after taking almost a year off from dating, and especially after being stood up on her date, she’s ready to get back on Seeking Arrangement.

“I have a PhD, so I like to look for men who are educated, who have work experience, I like to look at a certain type of man,” she says. “I think I’m ready now.”

When Sugaring Goes Bad

Just a quick scroll through the internet, and you’ll find stories from sugar babies with vastly different experiences. While some say they were able to make hundreds of dollars from every date and were lavished with gifts from their sugar daddies, there are also those who had a saltier experience.

One woman shared her experience being duped by a sugar daddy with the New York Times in 2018. After making good money going on dates with sugar daddies, one man had sex with her after pretending to send her $2,500 via PayPal. She later discovered he was on multiple dating sites, touting himself as a “sugar daddy seeking arrangement.” Then there are the women who recount receiving photos of men’s genitals, being asked to send videos of them pleasuring themselves, and proposals to set up weekly “meetings.”

“The first time I went on a date I was petrified. I chain-smoked five cigarettes and had scissors in my pocket,” a woman told The Independent about her sugaring experience.

“Even on a Tinder date, you can worry, ‘What if this person is not who they say they are?’ But this was not a date because one person might get some cash out of it or another might get something they want out of it.”

But unfortunately, this seems to be the lay of the land in the cyber dating world, where you don’t know who is behind the screen.

According to a survey by Pew Research, 53 percent of women 18 to 29 have received explicit images they did not ask for.

The online dating site Match started comparing users to sex offender registries back in 2011 after a woman sued the company when she was matched with a man who was convicted three times for rape. However, when the company expanded to include other dating sites such as PlentyofFish and Tinder, they didn’t keep up the practice, according to a study by ProPublica. There are no background checks or identity verifications on either.

On Seeking Arrangement, for a cost, members can opt to be screened for sex crimes, violent crimes, felony and misdemeanor assaults, domestic violence and the sex offender registry. Those who pass receive a badge on their account to alleviate concerns from other members.

However, those who fail are not removed from the site—members with “high-risk background failures will result in temporary suspension,” according to Seeking Arrangement.

In the cases of sugaring gone bad, the most extreme case was the murder of 23-year-old MacKenzie Lueck, a University of Utah student who was bludgeoned to death, burned and buried in the backyard of her sugar daddy, Ayoola Ajayi, 31. According to prosecutors, they met on Seeking Arrangement, and the University of Utah student was also on the dating sites Call Her Daddy and Tinder.

There are more than 3 million American students on Seeking Arrangement, and the top five majors are biology, art, psychology, nursing and business. In fact, when signing up for an account, those who use an .edu email address get an “upgrade.” The University of Central Florida, Florida International University and University of South Florida are in the top 10 universities for sugar babies.

This story is from the March 2021 of Boca magazine. For more content like this, subscribe to the magazine.