An all-expenses paid trip to Hawaii for lava-gazing chopper rides and dolphin kisses in sapphire lagoons trumps any dude asking, “Hey girl, what’s your sign?”

At least that’s what Donald says.

The 62-year-old San Francisco-based construction mogul whose dating profile rounds down to age 46 said he’s chasing fantasy. Among his roster of past relationships are three SF State students, aged 18-19. Aside from expected bouts with adolescent games and a number of young women perceivably fixated on the cash flow, Donald said life as a sugar daddy keeps the libido alive.

“Sex – when you get older, there’s a switch,” Donald said. “I don’t know what turns that switch on or off in my head. Believe me, I’ve done extreme analysis on this.”

Donald reports a net worth of $5 million and pays a premium membership for a verified account on Seeking Arrangement, a website that connects millennials with millionaires seeking “mutually beneficial arrangements.”

He said he’s looking for a live-in lady. Although he hasn’t found a roommate yet, Seeking Arrangement has matched Donald with plenty of bedmates.

“There’s a common thread among most of the females I’ve met on SA,” Donald said. “They’re either verging on nymphomania or they’re verging on non-orgasmic. And they’re looking for it. None of this has to do with ego. I’m a little more experienced than most guys. I’m older. Like the 18-year-old here on campus – she’s never had an orgasm with anyone except me.”

Donald said he took the SF State freshman shopping for housewares and they looked for an apartment in Parkmerced, but she backed out and told him she wasn’t looking for commitment.

“That’s the problem with an 18-year-old,” he said. “Straightforward, she’s fun in bed. But there’s not enough there to make it a serious relationship.”

The site’s advertisements specifically target college women, with a section titled “Sugar Baby University” that points out the rising cost of tuition and offers “a new way to afford an education.”

According to Brook Urick, Seeking Arrangement’s public relations manager, San Francisco is among the top 10 cities to find a sugar daddy. Approximately 7 percent of the site’s benefactors are sugar mommas and 10 percent of the site’s members are LGBTQ+. Golden Gate Xpress previously reported nearly 200 students at SF State have registered as a sugar baby with their .edu email address.

Brittany Cordero studied Seeking Arrangement as a student at California State University Sacramento, publishing her master’s thesis on “Sugar culture and SeekingArrangement.com participants” in 2015.

“What really dawned on me was how much language shapes your perception to fit societal norms,” Cordero said. “(Seeking Arrangement is) trying to push that the woman is empowered. The modern woman can get ahead. But the underlying premise is that the only way a woman can get ahead in this world is by the benefactor, a man.”

Cordero said Seeking Arrangement falls into a gray area and its use depends on each member’s intent.

“I don’t really know if it’s a good thing or a bad thing,” Cordero said. “I think it depends on what the woman makes of it. It really helps women if they’re in some type of education paying off loans, and I think that exemplifies something of our broken system. As long as costs like that are high and women are still low when it comes to the pay scale, we are going to continue to see things like this happen.”

Leslie, a 22-year-old SF State student whose name has been changed, recently registered on a whim.

“I was just like screw it, I’m going to sign up and see what happens,” Leslie said. “I figured I’m single, why not?”

Leslie said she was new to the online dating game and nervous to meet up with strangers.

“Coming into this, I (figured) they’re just going to take you to dinner and take you shopping,” she said. “Just have you as arm candy and then you can go home and that’s all they want. But 99 percent of these men are going to want you to sleep with them. You just have to think of what you’re comfortable with.”

She said she received 80 messages from potential suiters during her first week on the website, and “a lot of them were really creepy.”

“You’re beautiful,” one potential suitor wrote. “Come live with me in Dubai, all you have to do is be pretty and make scrambled eggs in the morning.”

Leslie met with three – a married radiologist in his 30s whom she never saw again; a 40-year-old CEO who stuck $400-$700 cash in her handbag each of the three times they met; and a 24-year-old start-up entrepreneur, who calls himself J, that she still hangs out with on occasion.

“He’s young, he’s cute, he’s blonde,” Leslie said. “I wouldn’t necessarily call that a ‘sugar daddy’ relationship. We’ll just go out to the club or he’ll take me to a show. He has good connections with companies around here and he has mentioned helping me if I want to find a better job… He’s never paid me, or anything like that.”

J’s Seeking Arrangement profile states that he’s “just here to cause trouble.” A self-proclaimed “womanizer” and “serial dater” who will give any dating site a try, J said Seeking Arrangement is his favorite.

“The average girl is much more attractive,” he explained. “The types of girls that are inclined to go on (Seeking Arrangement) are the girls that probably know they can use their looks to their advantage. These are the types of girls that have probably toyed with the idea of being an escort. This is like a little gateway for them, a way to still feel ethical about it.”

According to Seeking Arrangement, “college sugar babies receive an average $3,000 per month,” but J does not offer payment. Instead he foots the dinner bill or table service, something he said he would do with or without a baby on his arm.

“It’s easier to court women when you have the money for unlimited bar tabs and nice dinners all the time,” J said. “A lot of these girls just want a rich guy that’s fun and will take them out, show them the world, travel with them.”

Donald said he’s probably flown 10 different groups of “sugar babies” to Hawaii for sun-drenched romps on the Hilton Waikoloa’s white-sanded shores, but the mènage never worked out as expected until his most recent trip.

A Sugar Daddy holds his bottle of wine and his cash while showing off his watch as he poses for a portrait. (Connor Hunt/ Xpress)

A Sugar Daddy holds his bottle of wine and his cash while showing off his watch as he poses for a portrait. (Connor Hunt/ Xpress)

“It was a perfect fantasy,” Donald said. “Three very, very compatible females … to the point that I would probably be disappointed if I ever tried it again.”

When he got his driver’s license at 16, Donald said he was 4 feet 11 inches and underweight. He enrolled at UCLA at 17, where he completed three bachelor’s degrees in biology, chemistry, psychology and, later, a law degree. He said he didn’t get out much.

“I was more successful with my mom’s girlfriends at the disco who thought they were doing me a favor,” Donald said. “Then, I was dating older women. Now, I’m dating younger women. They were teaching me. And (now) maybe it’s a fatherly instinct, a mentorship instinct. It’s fun. It’s interesting. It keeps me on my toes. But I should probably go to sexaholics anonymous.”

Leslie said while she understands that sex is part of many sugar daddy relationships, it has to be on her own terms. She ended her relationship with the 40-year-old CEO after he made unwanted advances.

“Ending things before he had a chance to get more aggressive was the smart thing to do,” she said. “I just realized that I’m not attracted to this man, and when he was trying to make advances at me it made me feel sick to my stomach. That day, I left and I felt terrible.”

She noted that the situation hasn’t totally discouraged her from using the website. Seeking Arrangement reports one million active sugar daddies and mommas across 139 countries, and Leslie said she’s still curious to explore the options.

“I’m not looking for anything serious right now,” she said. “If I was, I would probably be more interested in dating traditionally, or people closer to my age. But that’s not what I want right now, so I might as well have some fun.”

Leslie said both parties maintain clout in the arrangement, but women have the edge.

“It’s supposed to be a mutually beneficial relationship,” she said. “But honestly, the women have more power. Men will do anything for an attractive woman.”

illustration by Kelsey Lannin

Illustration by Kelsey Lannin

Latest comment
  • Kim Kardashian breaks up with Kanye, now on honeydaddy