It’s a typical Saturday night at Yale. The line for Soads slowly slinks its way along the front lawns of Morse and Ezra Stiles colleges. Beer seeps through the open windows of dimly lit fraternities. Packs of students drunkenly stumble into GHeav for a $4 bacon, egg and cheese.

It’s a typical Saturday night, and Brian*, a junior at Yale, gets off the train at Grand Central Station to meet Richard, a 60-something-year-old Manhattan business type he’s been seeing regularly for months. Brian knows the drill: dinner, drinks, sex. In the morning they’ll cuddle and maybe eat breakfast, and then Brian will catch the Metro-North back to New Haven with $600 in his pocket. Brian needs financial help, and, for him, sex is just another means of getting by.

“People have sex because they’re lonely, because they’re tired, because they’re bored, because they want affirmation,” he said. “So, I was thinking about it, and I thought, ‘Well, why not do it for money?’ I mean, you’ve been dared before: ‘Would you eat dirt for $100?’ Well, why would you not eat dick?”

***

Brian isn’t exactly a prostitute, and neither is Emily, another student at Yale who spends her weekends meeting similar men in New York City. Brian and Emily are both “sugar babies” matched with older, wealthy sugar daddies on a website called Seeking Arrangement.     The website was founded in 2006 by Massachusetts Institute of Technology graduate Brandon Wade as a way to enable wealthy men without a “fighting chance” in the dating world to appeal to attractive young people through financial incentives. The site champions the slogan, “Relationships on Your Terms: Where beautiful, successful people fuel mutually beneficial relationships.” It claims to foster arrangements between sugar daddies seeking companionship and sugar babies seeking financial benefits — a give-and-take, symbiotic affair.

Critics feel differently. “Accusations of prostitution have clouded Seeking Arrangement,” Wade said in a statement published by CNN. “And I’ll admit there’s a fine line. But my intentions are pure.” He said that relationships are really an arrangement between two people: “My point is that dating is very superficial, so use every superficial means you have to get the attention you want.”

Seeking Arrangement has 4 million users worldwide, and its popularity is only increasing. The site is based on a membership system where sugar babies and sugar daddies and mommas create accounts free of charge and make connections by scrolling through lists of profiles and reaching out to the ones they like — an online shopping spree for the sugar daddy, rich and lonely, and the sugar baby, young and hopeful.

As of 2017, more than 1.2 million college students have registered as sugar babies on Seeking Arrangement. The site promotes its reputation as a “generous sponsor” of financial assistance and offers a variety of special services for students, including a free premium membership for anyone with a “.edu” email address.

In 2017, 44 million students in America took out loans to pay for college, amounting to a national total of $1.45 trillion of debt — a 560 percent increase from total student debt in 2004. Even Yale, a university that prides itself on a system of financial aid that meets “100% of demonstrated financial need,” still sometimes fails to relieve students of intimidating educational costs. Roughly 16 percent of Yale students graduate saddled with loans.

A monthly allowance given to sugar babies by sugar daddies can help relieve students’ significant college costs. Allowances typically range from $1,000 to $5,000 a month, with the average sugar baby making $3,000.

In her encounters, Emily has found that money is a way for sugar daddies to feel like they’re helping someone young to better their life — a kind of noble, philanthropic justification that eagerly anticipates the future success of the sugar baby they invested in. That’s the reason, she said, that sugar daddies are particularly interested in college students.

***

Both Brian and Emily first got involved with Seeking Arrangement at a time when finances were particularly tight.

“I first started out when I was about 19,” said Emily. “I was from an area of deprivation that I was trying to get out of. I’m not from a wealthy family, and even though I was working, and still I’m working three jobs, there was always a [shortfall]. … I couldn’t be at Yale if I didn’t do this.” For Brian, involvement in the industry came at time when he was “a little short on cash” but was also “just bored.” In the beginning, arrangements for Brian mostly consisted of talks on the phone, which sometimes evolved into awkward first dates predictably accompanied by bouts of forced small talk and out-of-pity smiles. It wasn’t until last spring that Brian started having sex with men for money.

Seeking Arrangement doesn’t call for strictly sexual relationships. Sugar babies and sugar daddies can specify whether they’re looking for nonsexual, or even online-only, arrangements. But, in the experiences of both Brian and Emily, sex is almost always implied.

“I began with the idea that it was just like going on dates and seeing what happened, and then I felt my way along,” said Brian. “I think it may be a gateway drug into prostitution. But I also think that if you want to go on and just meet people who genuinely interest you or show interest in you, then sure, you could probably do that.”

Arrangements typically begin with a bit of casual messaging through the website itself. Eventually, numbers are exchanged and the conversation transitions to text, then phone calls, then Skype and, if all goes well, an in-person date.

The first meeting often takes place in a bar or a restaurant and starts out like any ordinary date. But to Emily, courting in real life is very different from courting on Seeking Arrangement. Seeking Arrangement allows for “a lot more room to be yourself” and doesn’t leave much to interpretation. People are more self-aware and forthcoming and define the boundaries of the relationship right away. They know what they want, and they’ve come to Seeking Arrangement to get it.

“It’s more honest than        dating,” she said. “In real life, the more honest and transparent you are the more people are scared away, but on this, the more honest and transparent you are, the more attractive it makes you seem, which is so warped and backwards. In real life you’re expected to be someone different, but on this you’re expected to be nothing but yourself.”

There are limits, however, to how honest a person can be on Seeking Arrangement. Identities are often partially concealed, with neither sugar babies nor sugar daddies disclosing too much personal information. All users have their reservations, and no one is immune to the worry of being exposed.

Brian won’t share his real first name with sugar daddies, and Emily draws the line at contact through any form of social media. Both, however, prefer that sugar daddies share a decent amount of information with them before meeting in person. Just to be safe.

“I tend not to trust them if I can’t find information about them, but then I’m also very happy that they can’t find any information about me,” said Brian. “So it’s like a blind faith thing. It’s a relationship built on trust.”

For Emily, when sugar daddies withhold information, it is a definite “red flag.” She said it can sometimes mean that sugar daddies haven’t “processed their internal stigma or their internal self-damnation.” Or, worse, it can mean that they’re married and looking for a mistress on the side. She would know — it happened to her once before.

Risks are embedded in the network of Seeking Arrangement. Both Brian and Emily stress the importance of caution but agree that, as long as people know what they’re doing and are smart in social situations, Seeking Arrangement isn’t any more dangerous than typical millennial dating. Emily said that she’s felt “more threatened on Tinder dates” than she has on Seeking Arrangement and that even with the age difference, she fears 20-something-year-old males more than she fears anyone, especially in a college town.

***

Sugar daddies usually aren’t malicious people. Brian and Emily’s experiences suggest that more often than not, those looking for sugar babies tend to be exactly who you would expect: middle-aged white men who are, above all, lonely.

“You can actually form friendships,” Emily said. “They’re not just ATMs, they’re people.”

Richard, one of Brian’s sugar daddies, is married to a man who won’t have sex with him anymore. A Yale graduate from the class of 1977, Richard has achieved success in standard terms. But he’s lonely. So, on the weekends he travels to New York City and there, he meets young men.

“[Richard] loves to make very wry, nihilistic comments about how being an adulterer is so difficult, which says that he really does think about it,” said Brian. “Some [sugar daddies] are just lonely. It can be a little sad. But these aren’t terrible people. These are people who just want a relationship with a young, attractive, interesting person and don’t mind paying for it.”

But no matter how genuine the relationships may seem, when it comes to Seeking Arrangement, nothing can be removed from the inherent backbone of the industry: money.

“When money’s involved, you never can be entirely yourself,” said Emily. “That doesn’t mean you can’t be completely honest with your intentions, but there’s a certain aspect of your character that’s very different.”

Drawing the line between transaction and romance can be difficult. When an arrangement becomes fairly regular, it can be easy to get lost in the routine. For many sugar daddies, a relationship with a sugar baby can act as a kind of escape, or fantasy, that protects from the vulnerability of real-life dating.

“For men, there’s less chance of rejection when money’s on the line,” said Emily. “For all the women on [Seeking Arrangement], you’re kind of playing a role for [sugar daddies]. You’re presenting as the ‘ideal’ that is their escape; a satisfaction for them. You’re not there looking for a boyfriend. You’re there to entertain the idea of a romance.”

Brian, who often finds himself playing the role of the “ideal undergraduate,” said that, for sugar babies, the novelty can only last so long. No matter how much both people involved in the relationship try to pretend, the romantic bubble Seeking Arrangement constructs eventually pops. At the end of the day, money is still an underlying factor.

But actually talking about money can be taboo. In many arrangements, money is discussed once and not brought up again. In Brian’s experience, a lot of sugar daddies find it awkward or “distasteful” to talk payment and prefer to ignore its presence in the relationship altogether. Often times, money is paid electronically or presented in the form of a gift, creating the illusion that it’s not really there. Direct in-person transactions can be uncomfortable and embarrassing. Brian said that, in his experience, most sugar daddies “haven’t reconciled themselves with the idea of having to pay,” because money evokes the idea of prostitution too closely and shatters the idea of romance.

Money is a way Brian said he can “present himself as a product.” Usually, once something is bought, it’s owned. But in the Seeking Arrangement world, some men don’t like the fact that they have to pay for sugar babies because the purchase doesn’t entitle them to total power. For them, payment suggests they’re “somehow losing” and that the sugar babies might be getting more out of the arrangement than they are.

But for many sugar babies, money can be a way of quantifying their worth, seeing who out there finds them attractive — and just how much.

“There’s a huge number of people who have Tinder, and it’s not dissimilar,” Brian said. “Now [Tinder] has this thing where you can show how many people have swiped you, … and it’s very much like a buzz, it’s exciting. I have a lot of friends who are on Tinder just to see who likes them. See what your value is. [Seeking Arrangement] is not so different.”

“They always call us boys,” said Brian. He thinks it’s an innocence thing.

“On the male side it very much goes back to the Greeks and the Romans — the young male athlete, scholar. Like Antinous. He’s the third most statued person in the world after Zeus and Athena, because Hadrian was so in love with him that he had his face immortalized, which is pretty romantic. But he was 21 when he died and 14 when Hadrian first met him. So that’s definitely a part of this industry.”

Emily, too, said innocence is an aspect of the role she often has to play. But for her, gender is the means through which power is divided. 

Seeking Arrangement is notorious for touting arrangements between older wealthy men and attractive young women. So for Emily, a proponent of women’s rights, it’s been difficult to rationalize her position in the industry.

“I self-identified as a feminist for the first time when I was 4, so it’s obviously a really conflicting thing for me that I’m dependent on someone who has reached their position of power through means of their gender,” she said. “It definitely is a struggle because I guess a lot of the negative connotations [of the industry] are that it’s misogynistic men looking to own women.”

Older men on Seeking Arrangement often search for someone to fill the role of the submissive female or the damsel in distress. Some men derive satisfaction and empowerment from the feeling of owning and oppressing a younger woman.

It’s taken women years to claim a place in higher education, yet today, some still have to subject themselves to this kind of submission in order to stay. For Emily, however, the submission in arrangements isn’t always real. To her, it is just an illusion that allows sugar daddies feel like they’re in charge — but control in relationships is very much a two-way street.

Maintaining a healthy balance of power in arrangements is possible, but it hinges on establishing clear boundaries from the start and knowing when a relationship has to come to an end.

“The important thing is definitely boundaries,” said Emily. “Typically for me, if it’s an intense arrangement, it can last comfortably about six months. I’ve yet to have that ‘Pretty Woman’ situation where we fall magically in love. You’ve got to go in with a level head that that’s probably not going to happen. You need to say, ‘This can be romantic, and we can do romantic things, but this is not a romance.’”

***

One of the most difficult aspects of participating in Seeking Arrangement is rationalizing its place in real life. Those who engage in the industry fear they’ll be shamed and condemned if their identities are exposed. Most sugar babies only confide in their closest friends, if anyone at all. The world of Seeking Arrangement is highly complex and built on a network of controversial sentiments, but the industry is far more than just the stigma it carries. Many feel uneasy about the thought of older men purchasing the companionship of younger, often vulnerable, people. But this common stereotype oversimplifies the particular relationships at hand.

Emily doesn’t take issue with the fact that this is something she does. She takes issue with the fact that this is something she has to do.

“The situation that I’m in, the reason that this is something I need to do, is a man-made phenomenon,” she said. “I’m in this situation because I’m an extremely ambitious woman and my gender and my social class have denied me from achieving the means to pursue my dreams. It’s a social problem. And it doesn’t have to be like this at all.”

For many sugar babies, and for many college students like Brian and Emily, Seeking Arrangement is a way to provide a steady flow of financial income when other options have proven insufficient. It’s a source of means. Participating in the industry isn’t just a matter of making an account and having older men throw Fendi purses one’s way. It’s a lot more than that, and it’s a lot more common than people think.

In fact, the prevalence of sugar babies on college campuses has increased substantially in the last few years — a trend to which Yale contributes. Brian said that Yale has “pockets” of students involved with Seeking Arrangement, and that, “once you have one friend who does it,” others become curious and start to follow.

For many students involved in Seeking Arrangement, the industry is not a source of enjoyment but rather a necessary source of income.

“When you think about it, it’s kind of a messed up thing,” said one Yale student not involved in the industry, who asked to remain anonymous. “It’s hard to think that college is so cost prohibitive that it forces young people into prostitution.”

Of course, Seeking Arrangement isn’t always synonymous with prostitution. While some arrangements resemble sex work, Seeking Arrangement offers a platform for the cultivation of all kinds of relationships. It is not a one-size-fits-all industry — it is diverse in its intricacies and various in its intents. No one person has the same experience. It can be what you make of it.

Seeking Arrangement can come across as an elusive, glamorous and even sinister line of work, but at its core, it is really something that any student can relate to — whether it be the struggles of funding an education, barely scraping by to pay the rent each month or just the curiosity of seeing who thinks you’re attractive. Sugar babies are not virtual. They are real people with real intentions who think about what they do.

It’s typical a Sunday morning, and Brian arrives in New Haven on the Metro-North. He calls an Uber from Union Station and gets off at the corner of College and Wall streets. He heads to his dorm, takes a shower, grabs his backpack and walks to Bass Library. It’s been a busy weekend, and he has class on Monday.

*All “sugar babies” names are pseudonyms to protect their identities.