I Went To A Convention For Women Training to Find Sugar Daddies

I was welcomed to SeekingArrangement.com’s Sugar Baby Summit at the Avalon theater in Hollywood with a swag bag that contained one red tank top reading “Girls Just Wanna Have Fund$,” one Seeking Arrangement water bottle with a fruit infuser inside, one list of tips for safety when meeting my future-sugar daddy, and one course program for how I’d spend my afternoon at the Seeking Arrangement Sugar Baby Summit.

“Sugar daddies” and “sugar babies” are terms that start to sound normal by the time you’ve spent an hour at the Seeking Arrangement convention. The event, which was an all-day affair, featured three guest speakers — Jessica Chamberlin, Candice Kasha, and Ava Kinsey, three women who found successful and happy arrangements through Seeking Arrangement — to lend their expertise.

Much of the Seeking Arrangement dynamic is based on an “allowance” for women, and sex for the men, which the Atlantic reported in 2014, was something most of the women who are registered “sugar babies” have admitted to doing. So naturally, some people aren’t that into Seeking Arrangement. The New York Times wrote about the website in 2009, saying:

“Critics say the site is at best a convenience store for adulterers and at worst a virtual brothel, but Brandon Wade, Seeking Arrangement’s 38-year-old founder and chief executive, is unperturbed by the criticism. ‘We stress relationships that are mutually beneficial,’ he says. ‘We ask people to really think about what they want in a relationship and what they have to offer. That kind of upfront honesty is a good basis for any relationship.’”

The founder, who’s also been quoted saying, “love is for poor people” — he clarified for me later that he doesn’t actually believe this — was in attendance, but spent most of the time backstage giving interviews. Seeking Arrangement is only one of the ventures that the Singapore-born MIT grad is responsible for, but it’s one that’s close to his heart.

“I was bullied a lot in middle school,” he told me in an interview afterwards. “Until I realized that once I was successful, women would be more likely to date me.”

So there’s that. Anyway, the courses, which really just featured whichever speaker was on stage going over a simple PowerPoint presentation, were about building the perfect profile. Basically, her advice was, “be yourself.” Which like, on behalf of all of us in attendance, thanks, I guess.


“How long before I can ask for an increase in allowance?” was a question that got laughs during the second course, tailored to choosing the perfect outfit for a first date with potential “diamond daddies.”

Next was the messaging breakdown.

“If you like a guy,” one grown woman got up and asked, “how long should you wait for him before starting to message other guys?”

“If he’s not making plans to see you within two weeks, move on,” the speaker advised. Sure, why not, right?

“As a brown girl, what can I expect from Seeking Arrangements?” another woman asked later. “Are sugar daddies as open to dating African-American women as they are to white women?”

The speaker was a little thrown, and the whole interaction was pretty painful to witness.

“I’m honestly not really sure,” she said. “But I think you should embrace your uniqueness and differences — they’re what make you you!”


I snorted and ate another free Avalon theatre chocolate chip cookie. During the lunch break, I approached the girl who asked the question to see if she felt like her question had been answered.

“Well, no,” she admitted. “But I don’t blame her, ’cause she clearly just doesn’t know since she isn’t black. But I guess I just don’t look at being black as something that’s different or unique about me.”

She told me she was taking classes at community college in Palm Springs, and had been researching her options for making money. She had been debating between signing up for a SeekingArrangements profile, and becoming a stripper. I thanked her for talking to me, and got in line with the rest of the sugar baby potentials for some free lunch, then sat in the auditorium with my grilled veggie sandwich.

Although most of the day’s activities were downright depressing, looking around, I realized the whole vibe of a room filled with women was pretty chilled out, and even kind of sweet. The sugar babies were all just hangin’ out, eating free lunches, enjoying their swag bags. Women are awesome, I thought. We’re all just in one room together, being friendly to one another. 

And if you think about it, online dating as a sugar baby isn’t all that different from regular online dating.

“We turn ourselves into commodities, typing up dating-site profiles as if they were product descriptions, placing orders on one person and disposing of the next with a single swipe,” Alexandra Schwartz wrote in a recent New Yorker article on the brief history of online dating.

It’s hard to judge people when they’re right in front of you, and when you’re all together at the same Sugar Baby summit, eating free grilled veggie sandwiches together. There definitely was something terrifying about so openly placing monetary value on each of the women, and what they could offer to a relationship. When I walked out of the theater that day, I saw one of the women who’d asked if it was reasonable to age herself for her profile, in order for her potential daddies to be pleasantly surprised when they learned she was actually in her forties, and not fifty, like she claimed. That could be my mom, I thought. It could be any of us.

So is Seeking Arrangements any weirder than any other platform of online dating? It’s hard to know. Dating itself is complicated these days, and if anything, Seeking Arrangements is just one of the many manifestations of the ways in which we’re taught to relate to love, money, and our own value and or worth. And I wouldn’t want to assume anything about why, or how, or in what ways any women relate to those things. Because after attending the Sugar Baby Summit, I’m not interested in judging anyone. After all, I was there too, I also appreciated free food, and I probably enjoyed it as much as they did.

Gimme More Dating

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