Sugar Daddies And Sugar Babies

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*All of the names used in this article are fake names, for privacy reasons.

When Tiffany* moved to Hawaii a couple of years ago, the decision was so spontaneous that she booked her ticket while vacationing in Florida and came straight here without even stopping home in New York first. Of course, arriving in a new city with nothing lined up was tough. She initially lived in a hostel while working as a cocktail waitress.

But after just a few months, Tiffany was living in a nice house, driving a nice car, and working at a vacation rental company.

The turnaround was all thanks to Adam, the owner of the vacation rental business, a man whom Tiffany calls her sugar daddy.

The two met on SeekingArrangement.com, a website that boasts that it facilitates relationships that are “mutually beneficial.” Put another way, it connects young, attractive people (sugar babies) with older, more established ones (sugar daddies/mommies). In the case of Tiffany, now 27, and Adam, 50, she provided him with a pretty, fun young companion, while he paid for her living expenses.

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The trope, of course, is a familiar one. Young, hot girl. Rich, older dude. And online, a cottage industry of niche sites like Seeking Arrangement — there’s a whole slew of them, including Arrangement Finders, Sugar Daddies, Established Men and more — has sprouted up around the concept.

An obvious magnet for controversy since they started appearing in the early 2000s, these sites attract both enthusiastic supporters and fervent critics. But despite mixed public opinion, these sites have drawn in millions of users worldwide, including hundreds here in Hawaii.

The appeal of these sites seems to be founded on a sort of magic bullet, a promise of a better future for everyone — for the daddies (and it is mostly daddies versus mommies), it’s a form of companionship or a break from midlife boredom; for the sugar babies, it’s financial stability and a bit of sage advice. And while many users tout that these sites offer a more straightforward interaction than the murky waters of traditional dating, the reality may be its own clouded pool.
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On Tiffany’s first date with a former sugar daddy, years before she met Adam, he flew her to his hometown in Texas for a weekend trip.

He booked them a suite in a swanky hotel, took her on a tour around the city, and treated her to a $9,000 shopping spree ($1,200 just at Victoria’s Secret alone). At the time, Tiffany lived in Tennessee, and they’d commute once a week to see each other, on his dime of course. She also accompanied him on business trips (she’s not really sure what he did for a living, “computers or engineering, something techy and really high up there”) to places like New Orleans, Atlanta and New York.

“All he wanted to do was spend money on me,” Tiffany recalls. “I got my own apartment, I had a sweet car, he was paying for my clothes, my cell phone, I would have my nails done every week. I was spoiled rotten.”

Sugar babies often detail such extravagant treatment — designer bags and clothes, cars, even apartments — but their foray into “the sugar bowl,” as the lifestyle is called, is often out of something more akin to desperation than greed.

For 21-year-old Emily, staying in school at a local college was a top priority. But working a full-time, low-wage job while taking a full course load became grating after a while. Her situation reached a head when she had to pay off a loan, so she signed up for Seeking Arrangement and Arrangement Finders. She tries to keep things online — sending suggestive pics and flirty messages — in lieu of an actual meeting, and just talking to a few guys via text has helped pay off some of her bills.

“I was super burned out,” Emily explains. “I have sent pictures for less, so if somebody wants to give me a grand for that, great.”

Julie, 25, was taken aback at how expensive the cost of living is in Hawaii when she moved here from the East Coast a few years ago. She was still in college when she met Michael, an entrepreneur she guesses is in his mid-40s, on Seeking Arrangement. While they never exchanged cash directly, he paid her rent, and often paid for her to jetset around the world with either him or her friends.
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“He made it possible for me to stay (in Hawaii), really. If it wasn’t for him, I don’t think I would still be here,” says Julie, a law student.

“People at this age feel like they are scrounging when it comes to student loans, trying to graduate, getting an adult job,” Julie says. “I was in that position, and I felt like I couldn’t breathe. I really look at it as someone helping me get out from under.”

It was Michael, Julie points out, who encouraged her to apply for law school in the first place. When she was struggling to make the decision, he sat down with her to make a list of pros and cons. Much like, Julie muses, a parent might. In the end, he offered to pay for her first year to see if she likes it. She ended up loving it.

While Tiffany is now used to upscale living, when she first signed up for arrangement sites several years ago, she was crammed into a three-bedroom house with 10 people. She subsisted on ramen. She was trying to pay her way through college. So when a friend told her there was a site where rich guys pay your bills, she was intrigued.

“I was like, that seems kind of too good to be true,” she recalls.

Of course, not all experiences with sugar daddies are positive ones. Tiffany has been stood up, had a guy pick her up high on cocaine (and really angry that her hair wasn’t quite as blonde in person), and gifted a credit card only to find out there’s no money on it.

Then there are the fake profiles. (“If they have a six-pack and they are 27 and they say they make $5 million, bull-f***ing sh*t,” Tiffany advises.)

Then there are the con men. Emily had a guy trick her into sharing her credit card information — and then steal what little money she did have.

And then, of course, there are the weirdos. “I had a guy tell me one time,” Tiffany recalls, “‘I’ll swallow a key and you cut me open. If you find it, I will give you $25,000 dollars.’

“If people say that girls are on there to be prostitutes,” Tiffany says, “then guys are on there to be f***ing weirdos, too.”

Seeking Arrangement founder Brandon Wade often has lamented in interviews that he didn’t kiss a girl until he was 21. Graduating from MIT and landing a six-figure job didn’t change the fact that he was shy and awkward. He figured the one advantage he did have was wealth, so he created Seeking Arrangement as a way to advertise his assets.

“I think all relationships start off in a very superficial manner,” Wade told Business Insider in 2014, just one in a string of controversial, unapologetic interviews. “For men it’s a visual thing … Women tend to look at men in terms of how successful they are, what sort of job they have, how much money they make.”

Fairly new to Seeking Arrangement, 39-year-old Brian, who works in IT, talks about his dealings on the site in Wade’s cut-and-dry manner. For now, Brian has been feeling things out, going on a few meet-and-greet lunches with potential babies. He insists that he is looking to build a friendship of sorts, but he has found the women he’s been meeting and greeting have a “non-willingness to work with me. Most of them throw out a really big number; they come across as lazy. They want something for nothing.”

In detailing the follow-up of one lunch, he says this: “She texted me that she wanted way too much money just to meet again. I tried to negotiate, but she just called me cheap.”

While Adam echoes that all-business approach in our interview — “it’s just a very simple format; you don’t have to play games; we know what we are there for” — his profile hints that he’s looking for something a little more stable. While many daddies’ profiles make sly winks about “having fun together” Adam writes, “transactional arrangements are not for me. I wish to look after, and be looked after, by an equal partner.” When I ask him about that, he admits that he wants a situation that is “just like a normal relationship.”

“I need a companion,” he adds. “The girlfriend experience, if you will.”

But why the girlfriend experience and not an actual girlfriend?

Well, he explains, he is on Tinder, too, but he hasn’t had much luck there.

Brian admits that one source of frustration has been that the girls under 25 he’s been talking to have been particularly unreliable. He seems genuinely confused when I ask him why he’s only looking for a woman who is 30 or under.

“Why would I want to date a woman my age?” he says.

He laughs when I ask him why not.

“It feels too serious,” he says.

Anything serious, after all, seems to be the antithesis of being a sugar daddy or baby. Many profiles say they’re looking for someone to share in the pleasures of life, not its drudgeries. (A number of sugar daddies, after all, have wives for that.) The role of the baby, then, is almost a sort of cipher. If this could be looked at as a job, then it is on the sugar babies’ list of responsibilities to be what daddy is looking for, when he’s looking for it, while simultaneously not taking up too much space in his life.

As Julie neatly sums it up: “We don’t necessarily work for them, but we are there for them when they want it. And they don’t have to call us every day, text us every day, or come to our house every day.”

There does seem to be, in principle at least, a gap between, to borrow Adam’s phrasing, “date-y things” and actual dates, between “the girlfriend experience” and an actual girlfriend. But it’s a distinction that tends to get blurry, often seeming more complicated than perhaps the users anticipate.

The way that Julie talks about Michael, seems, for all intents and purposes, like any boyfriend/girlfriend relationship. They saw each other for a year and a half, often traveling together and spending quiet nights in cooking dinner. Even now, she can’t seem to say enough good things about him and admits she misses him.

But when I ask if she was in love with him, she responds swiftly: “No. No, no, no. Uh uh.”

Still, she struggles to definitively elucidate the relationship.

“I depended on him, no doubt,” Julie says. “But I didn’t think of him as a sugar daddy. I was in a relationship with him. But it was an arrangement.

“You go into it knowing that it is not going to last forever.”

It might have been money that drew Tiffany to Adam — when they first started talking, he said, “I will pick you up in one of my cars” — but over the course of their relationship, that changed. Tiffany became his business partner, and when they weren’t working, they spent their days at the beach, going to lunch and canoe paddling.

“He became my best friend — it was so weird,” Tiffany says. “He would make me laugh, like I-can’t-breathe laughing. Just being around him made me happy. It was really cool.”

Things between Adam and Tiffany ended amicably — so much so that she continued to live with him even after their arrangement was over.

After that, Adam took some time off from the site — he was having business troubles and had to cut back expenses — but is now back and looking for a long-term baby.

While things had not yet gotten physical with a potential new baby he’s been seeing at the time of our talk, it was something that had been hinted at, something he was hoping for. But, for Adam, even having her come over for a sleepover recently — she stayed on the couch — was exciting enough.

“Her dog got to meet my cat — it was like a little family,” he says with a laugh.

It is worth noting that no one I interviewed for this story brought up the most obvious topic, sex, until I asked about it directly.

While it seems that members rarely spell that out in their profiles, there is an underlying subtext on these sites that a physical relationship is a possibility, if not quite an expectation. Some users I talked to say that they have had relationships cool once it’s evident that sex isn’t on the table.

Julie says, though, that she “runs a tight ship,” and that sex is never part of any of her shorter arrangements. “Some of them expect it, for sure, but I make it pretty clear that that is not what this is,” Julie says.

Tiffany has been intimate with all of her sugar daddies. She insists, though, it’s by her own volition. “I don’t feel used or pushed to do anything,” she says. “I want to.”

But what about the men she’s not attracted to?

“If I’m out with someone and I am not attracted to him, I just try to think about why I am doing it and what I need it for.”

The central argument against arrangement sites is that they are thinly veiled escort services.

While the sites manage to sidestep any legal issues — none of them promote the exchange of sex for money — they can still, critics argue, be a gateway to more nefarious activities.

Three years ago, Pacific Alliance To Stop Slavery founder Kathryn Xian brought an 18-year-old into the PASS safe house. The girl had signed up for a sugar daddy site hoping to find a rich boyfriend to take her away from a rough family situation. Instead, through the site, a sex work recruiter lured her into a Waikiki hotel, where she was held against her will and forced into prostitution.

Xian says that situation is not uncommon. Pimps and traffickers, she explains, can post pictures of their girls through the site, acting like they’re just poor students in need of rent money.

“Whatever argument these dudes or the creators of these websites have … holds no water,” Xian says. “Nothing they can argue can dissolve the fact that women and children have been trafficked on these sites.”

Tiffany is adamant that the site has done nothing but good things for her.

That’s why it catches me by surprise when, toward the end of our conversation, she says this: “I would love to be just a super strong, rich, independent woman where I don’t need help.”

Eventually, she says, she does want to get off the site. She paints a scenario where she’s wakes up in the morning, looks around, and knows that everything around her is there because she worked hard for it. And that everything she has is all hers.

But then she snaps out of her daydream.

She could do that all on her own, she knows that, of course, she could. She even knows the steps she would take. “But I would have to go back to school and that is more money. And then once I do that, find a job, advance my career, work for years and years to get to the top.”

Right now, things are going well for her — she’s making decent money at a new hotel job. But the dreamy way she talks about her future, it sounds, well, just like the way anybody envisions their own future, really — distant and ultimately unknowable.