But life had a different direction for me: an opening. An opportunity to get it together and figure it out. And it all started with a close friend named Em. A girlfriend of mine who I’d traveled through the world of academia with who, at the time, was living on her own in a one bedroom apartment in the Tenderloin. A block away from Civic Center and two blocks away from Powell and Market, an ideal location for familiarity. “You can stay with me while you find a new place, dorms suck man LOL,” she wrote to me. A saving grace for my catalyst fear of returning back to my small town—she gave me chance.
The plans were set, my bags were packed, and I was to move in May of 2015. I was given the futon in her living room and three months of unpaid rent, “I got it covered, no worries, just stay on my couch till you find something.” I was lucky. As I began to pack up my longest standing home since moving away from Washington, I began to pair down the variety of tchotchkes lining my walls and shelves. “I need to be light and nimble, Em doesn’t have much space for me,” I thought to myself wrapping up my treasures in old newspapers.
Who is Em? Em is a jewel covered box of a personality—someone who you can confidently confide in. A woman who lived life on the edge. She threw danger to the wind, and the wind guided her every move—she floated with a sense of urgency. In a matter of minutes, you were Em’s newest friend. Though Em was petite and stylish, she a boisterous laugh, a full figured smile, and sharp wit. An alpha female through and through. Em and I had always clicked like that. Working together on a variety of photoshoots, getting her included on projects, and she never complained. She always wanted to collaborate and never shied away from the action. I was elated to move in with her—our synergy had always been on point when we could hang out and grab a bite to eat. A summer together creating made me excited.
As it was time to move into her apartment, it was typical of what I could picture her mind being. Her spot was located in the heart of the Tenderloin, though not the cutest part of town, it had a lot of history and rich culture. Herself full of knowledge for most subjects and if she became interested in a topic, she would research every part and angle of her target until she became fluent or an expert. As you stepped into her apartment, you could tell an art student was living in it. Mismatched art pieces lying around, art hung haphazardly on the walls. My new home, the futon, laid up against the bay windows that faced the corner of the heart of the Tenderloin while she slept in the adjacent room shielded by folding wooden doors.
Her room, filled to the brim, with art supplies, sketchbooks, clothing, action figures, designer clothing and bags, luxury makeup sprawled across her crisp white comforter—it was a mess that only she knew where things lived. It had looked like she had moved the entirety of her apartment into the confines of her room.
“Ok, so this will be ok until August but after you gotta find a new spot” she told me, “that’s fine with me” I responded.
“It was agreed upon and I knew my time in her space was temporary. But Em’s excitement of having someone else in her apartment kept my stay interesting. So cohabitation was fun.”
It was agreed upon and I knew my time in her space was temporary. But Em’s excitement of having someone else in her apartment kept my stay interesting. So cohabitation was fun.
One month into my stay, after searching around for a space in all districts of the city. Em and I were as thick of thieves could ever be, watching movies at home together, ordering Japanese takeover from her favorite spot in the city, having fun art parties with her closest and coolest friends. And in between I had started to notice her going out on more and more dates, she would get dressed up for evenings to the Opera, nice dinners out, weekend trips to other cities. Her go-to going out look was a sleek black dress and a pair of Louboutins, her signature Vivienne Westwood knuckle ring, and a blue undertone red lipstick. Sometimes she would dawn a chocolate brown lace front wig to cover her artificial ice cold blond hair. Em would leave the apartment in a hurry but was promptly home at the same time in the evening. It had got me wondering, “who was this boy in her life that’s treating her so nicely?” I approached her about who she was seeing, was he cute?
“Oh, maybe I should have told you, haha, I have a guy who pays for my living, school and expenses” she told me bluntly.
“A sugarbaby? You have a sugar daddy?” I asked skeptical over our weekly takeout.
“I would call him an investor of my future” she said stuffing her mouth with rice. It had started to make a lot more sense—our apartment was always littered with the luxuries of life—it was stepping into a jewel box from an already rough Tenderloin. Boxes of La Mer skincare lined our bathrooms shelves, Celine bags filled with lord knows what. It clicked in that moment. By day, a regular art student who’s ideas and hustles couldn’t be contained—by night, a girlfriend to some of the Bay Area’s most wealthy. I was living in her spoils, in the physical objects of others desire for her.
“By the way, I’m heading to Florida for the weekend with him so you have the place to yourself, no wild parties while I’m gone,” she said, finishing the last drop of her miso soup and walking back to her $4000 Wacom tablet. Everything clicked. While I thought she was well off from family, she had been hustling men for their bottom dollar.
“So do you have sex with them or like… is that safe?” I asked in concern for her.
She looked at me from her drawing station, “I don’t touch them and they don’t touch me—I set the stage for what happens.”
The night was then filled with questions on the how, the where, the when. You read about sugar babies on tabloid websites, you see them on Instagram flaunting their earned wealth, you never get to really sit one-on-one with them but some things are closer to home than you imagine.
“So you’re not a hooker or something?” I ask with a general sense of curiosity in my voice.
She begins to belly laugh curled in her computer chair, “Bruh that’s wack.” She reaches over Wacom for a tube of red Chanel nail polish and begins to paint her toenails.
“How did you meet this guy? How does one become a sugarbaby?” I ask.
She begins to answer me while not averting gaze from her toenails, “Seeking Arrangements.”
Yes, the 2 A.M. infomercials that came on after the TV channels would go into advertisements only throughout the night.
But I needed to know more and Em wasn’t shy nor did she ever hide it from me—I mean, the riches of life slept next to me on her store-bought Ikea futon.
“I mean, the riches of life slept next to me on her store-bought Ikea futon.”
“He hates that I live in this part of town, if he had the choice, I’d be living in a nice house in Burlingame.”
Again, not averting gaze for the precision of her red polish—every drop counts I guess.
“Wait, like a HOUSE in Burlingame or like an apartment?” I questioned.
“No, a house,” Em laughs as I ask with uncertainty.
“Not everyone’s cut out for being a baby though, some people give it up to quickly and then you have nothing to show for it.”
I looked at her with confusion, she looks up to my quizzical face plastered sideways, “like having sex” she adds on, “I don’t have sex with him and I don’t let him touch me inappropriately because then he’s gotten everything from me—I try and retain a shred of mystery, I keep him on his toes.”
Without skipping a beat, she adds, “I might get a third investor here soon, I’m trying to build.”
My eyes wide, “you already have two sugar daddies?” She looks up at me with a smile, “investors babe, investors.”
It got me wondering, what is the sugar baby community like? It’s not everyday you’re sitting cross-legged hamming down Japanese teriyaki into your mouth. My initial thought of a sugar baby was someone who flaunted the enormous wealth through physical items. Louis Vuitton bags, Gucci slippers, flying in and out of the country on a private jet while eating only nothing but caviar. Em was not the picture norm sugar baby but on the other hand, she definitely didn’t live the average sugar baby life. The number of university students in the United States seeking sugar daddies and sugar mommies rose 44 percent from the previous year states Seeking.com on it’s highly successful business model. But what is Seeking.com, you may ask, SeekingArrangement is the world’s largest dating website that facilitates open and honest relationships. Founded in 2006 by MIT graduate and “relationship innovator”, Brandon Wade, the website now has 20 million members worldwide.
On average, babies receive a monthly allowance of $2,925 among other benefits, including networking opportunities and career or business advantages. On the contrary, it’s not uncommon: In the US, more than 42 million Americans have student loan debt. Meanwhile, the average debt per student rose by 5 percent in 2018 to nearly $40,000. Seeking Arrangements (Seeking, for short) has even addressed the ongoing student debt crisis with linking up students with sugar daddies and mommies with it’s Sugar Baby University.
So maybe, this was the best solution for Em. Her and I both attended the same private art school and tuition prices were not cheap in the least. And possibly, this was doing good for her? “Students registered on SeekingArrangement get help paying for tuition and even more benefits,” says the University’s website, “finding the right Sugar Daddy can help students gain access to the right network and opportunities. College Sugar Babies can also get help paying for other college-related costs, such as books and housing”
We got even more clarity from the Seeking team about how sugaring can be a viable option in the first place, “student loan debt in the United States is increasing at an alarming rate- quadrupling from the year 2004 to 2017,” the Seeking team tells us, “meanwhile, Education Secretary Betsy DeVos is seemingly waging war against tens of thousands of student loan borrowers. Rather than look to Washington for relief, more than two million students are turning to Sugar Daddies and Sugar Mommies.”
They keyed us into more shocking information, “the number of college graduates carrying student loan debt is higher than those who are employed full-time. Instead of waiting to see if a new administration might bring relief after the 2020 elections, an increasing number of students are counting on wealthy benefactors to help fund their education. SeekingArrangement is releasing its annual findings on the “Fastest Growing Sugar Baby Schools.” Over 2.5 million of the 20 million members on the world’s largest Sugar Daddy dating site are American college students. The average yearly cost of tuition and fees at a public, four-year institution has more than doubled since 2001 to $9,510.”<blockquote data-animation-role=“quote"data-animation-override>“Students are tired of hearing politicians campaign on the importance of education, job growth, and opportunity-just to leave promises on the convention floor.”— Brandon Wade, CEO and Founder of SeekingArrangement
“Over the past three administrations, the overall cost of attending college has more than doubled. Students are tired of hearing politicians campaign on the importance of education, job growth, and opportunity-just to leave promises on the convention floor,” says Brandon Wade, Founder and CEO of SeekingArrangement. “The numbers speak for themselves. Of the four million students on SeekingArrangement, more than 62 percent attend college in the US.”
data-animation-override>“Students are tired of hearing politicians campaign on the importance of education, job growth, and opportunity-just to leave promises on the convention floor.”— Brandon Wade, CEO and Founder of SeekingArrangement
Em wanted to focus on her work, she needed to pay off school and with the workforce turning artists into one-time contractors, paying for university out-of-pocket seems near to impossible.
And for two more months living in our Tenderloin jewel box, Em was showered in gifts and trips while I received the luxe run-off. Free face creams, jewelry she didn’t want, and more—the sugar radiated out. So much so, that Em gave me a goodwill loan (offered by her investor) to help me secure the first month’s rent and deposit so I could move into the Richmond district. And what do I have to show for it? While I worked hard and hustled, Em did her own hustle that was fully funded by the support of others—I don’t envy her. I find it fascinating that men of all different age ranges desired her, that someone felt so compelled to shower her in whatever she desired, her whisper was their command.
As I look back fondly of our late night Japanese binges in her Tenderloin apartment, I’m humbled by the fact that she never flaunted the wealth and claimed inheritance in my face. Em had always been a friend first and not some lap of luxury trendsetter that used money against me. Oddly, that’s what real friendship is like. She, like a real businesswoman, kept her riches to herself. Some would say a wolf in sheep’s clothing, but to her, that would be a sincere compliment.
// Illustration by Illustration by Christian Leon Guerrero; have a story you want to share with us? Send us an email to editor@bobcutmag.com. We’re dying to know.
