My Best Friend Is a Sugar Daddy. What Is That Like?

First, the numbers.

44: age of my best friend, John

150–200: number of women he has dated since August 1, 2016

2: average dates per week

9: most dates in one week

60: number of women he has slept with in that time

48: his oldest partner

17: his youngest partner (her profile said she was 18, officer!)

$12,000–15,000: what John has paid these dates. I don’t mean the price of the outings, the meals and movies and tanks of gas. I mean the — well, it goes by several names. Stipend. Allowance. Per-meeting cost. It is a strange lifestyle, one of transactional affection, torts and tickers, ships that pay in the night, dinner and a movie not as foreplay but fee harvesting. My best friend is, in short, a sugar daddy.

Sugar daddies have been around for ages. The term is an amalgam of “sugar,” a slang term for money, and “daddy,” a reference to an older man, and it dates back to the 1920s. The last few years have seen a rise in interest in sugar culture. A Google search for “sugar daddy” turns up nearly 2 million results, with “sugar baby” yielding another 3 million. Articles about sugaring have appeared in Vanity Fair, Slate, Cosmopolitan, Huffington Post, and the New York Times. Thought Catalog dives deep into the subject with “The 10 Golden Rules of Sugar Dating.”

Money is, of course, the cardinal rule, but not all sugar babies are Melania Trump types seeking pampering at the hands of billionaires. About half are working their way through college. Others are between jobs, struggling with debt, or simply interested in older men. Whatever their motives, sugar babies are having a moment.

It takes two to Venmo, however, and few writers seem interested in portraying sugar daddies as anything other than rich and powerful Bruce Wayne wannabees. John is not in his 60s. He is well-off but not wealthy. He doesn’t sit on corporate boards, have box seats at The Met, or own a tuxedo. The only person who paparazzos him is his mother. He got into sugaring not for arm candy but to mitigate the risk of getting hurt (more on this later). He finds his babies on Seeking Arrangement, the first and best-known sugar dating site, which was founded in 2006 and has over 3.5 million members, according to some sources.

He joined the site in 2016, and in a little less than two years, he has, in his words, “felt all the breasts — big, small, flabby, perky, fake, real.” Most of the women have been under 30. Many were under 25. He’s dated college students, single moms, middle-agers, and a married couple. Redheads, blondes, brunettes. Asian, African-American, German, Brazilian, British, Mexican, Moroccan, plain old Southern. A bartender, a biochemist, small business owners, exotic dancers, office workers, an engineer, a lawyer, a nanny, “between jobs.”

A fashion model.

A former Playboy bunny.

As with any dating, there have been ups and downs. One woman excused herself during dinner and never came back. One kept texting her father all night, including to ask him what she should order for her meal. One threw up on his bathroom floor. One got drunk, made a list of his flaws, and said she couldn’t wait to see how big his penis was. Some were into bondage, some into DDLG, and one in California still says she is in love with him. They have never met.

I have known John since 1990, when he walked into my eleventh Spanish class and took the seat next to me. After high school, he needed to find himself, so he worked at a die-casting plant, then as a corporate headhunter. He owned candy dispensers, sold perfume, and answered ads where neither the job nor the company was identified.

Finally, in 1996, his mother and stepfather made him an offer: go to college now; we’ll help you pay. He graduated in three years with a degree in nursing home administration. Most people burn out on that career in a few years; John handled it for nearly twenty before buying his own business. He is hard-charging, competitive, and a little vain: he gets blond highlights and dresses like an Esquire cover model. Though he managed a $250 million portfolio of nursing homes, it takes him an hour to pick out a pair of jeans. He says “yellow mustard” instead of just “mustard” and pronounces “mirror” as “mere.” He stands on a towel to use a hotel shower. He polishes silverware before using it and removes his shoes even if he will be home only a few minutes. When we watch a movie on Netflix, I can’t concentrate because he is reading magazines, typing emails, texting, or clattering in the kitchen. We seem to be as well-matched as Somerset and Mills in Se7en, yet people think we’re brothers, or lovers (spoiler alert: we’re not).

After his divorce from his first wife, Amy, he tried for two years to reconcile with her. She played him like a harp from hell, bilking him freely, withholding their two sons, dating other guys while sleeping with him here and there. “I deserve it,” he said soberly, “because of what I did to her”: a three-month affair with a co-worker. We have seen each other through a number of scrapes since then, including the end of his second marriage, to a woman named Sarah, in 2015, which shook him in a way I had never seen.

Wary of marrying a third time, but not wanting to spend evenings alone, he tried traditional dating websites with bleak results. Then he met Alicia, a 35-year-old law school graduate working as a part-time paralegal. They texted a bit, and Alicia asked him what he was looking for. Marriage? Dating? Arrangement?

The word “arrangement” got him curious. He asked what it was, and she replied, “Don’t play stupid with me.” He assured her he was not playing. She explained it as “you get all the advantages of a relationship but none of the disadvantages.”

How does it work? he wondered. “Like what if I wanted to spend the whole weekend with you? Or just a weeknight to relieve some stress? Or a phone call to hear about your day?”

“Well,” she replied, “I guess it just starts with an upfront amount. We hang out, eventually go upstairs, wink wink.”

They agreed on $300 but did not meet right away. Two weeks passed of questions and answers, silly texts, naked flirtation, naked pictures — typical connection testing for new lovers. Finally, John was ready. On August 1, 2016, he took pizza and beer to her place, not because he likes either, but they are what she requested. When he got there, she was smoking pot. He had never tried pot, but he was so jittery he had some. Why was he nervous? “I didn’t know if she would turn out to be a cop and bust me.”

They talked a while, then she indeed wink-winked him upstairs. She offered to let him spend the night and have sex again in the morning for another $300. Erasing his nervousness, he dickered her down to $100, and they had sex twice more. Amazing.

After that night, John wasn’t sure he wanted to see her again. He had come on too strong, calling her beautiful and smart, spelling out kisses in his texts (“Muah!”), saying he was “pissed off for her” when she told him about a bad day. It was dating language, his default lexicon, but he didn’t make sure he liked her first. Besides, he had just paid for sex: that takes getting used to. Millions of first dates don’t lead to second dates, but when John tried to let her down easy, she rage-texted.

“I invested time on what I thought was a promise.”

“I have $37 in my bank account as of today.”

“I have no other source of income.”

“You owe me!”

When she got down to naming the meager contents of her cupboards, he offered to send her another $100. She was grateful, but their relationship didn’t recover. He felt guilt-tripped, and she felt betrayed. Her assessment — “all the advantages of a relationship but none of the disadvantages” — didn’t come to pass after all.

At first, sugar dating is a lot like regular dating: you have to find someone you genuinely like and want to spend time with. This is the biggest difference between sugaring and prostitution. Sugar babies also have a more varied job description than prostitutes, needing to stay current on politics, sports, maybe the arts, so they can, you know, talk to their daddies.

Conversational prowess is probably the number one thing John looks for. He equates strength with intelligence and is most attracted to women with graduate degrees because “a degree is evidence of their ability to achieve something.” Who are a good conversationalists? Women who are “aware of the world around them.” Pop culture, society, careers, politics, religion — these are all topics he likes to discuss. And he likes when women ask him questions. “Otherwise,” he says, “it’s just an interview.”

Sugaring is not as easy as it looks, for babies or daddies, who also have a learning curve. Daddies need to possess negotiating skills. Understand the different kinds of relationships. Know the different fee structures (he now does per-meeting fees exclusively, as do about half of sugar daddies, after getting burned on a few allowances). One thing that surprised John was how many potential babies didn’t want money. Was it youthful experimentation? Did they have daddy issues? Or do they simply prefer older men?

Some would call John a predator. They assume that no young woman can date an older man without coercion. I think exploring sexual agency is empowering, perhaps making that another attraction of the sugar lifestyle. One of his dates, for example, was a 22-year-old grad student in North Carolina. He flew up there from Florida, where he lives, planning to make it a real date — take her to dinner, go hiking, go to a play, whatever.

He was supposed to meet her at a restaurant at 1:30. At 2:00, she hadn’t arrived. This sort of negligence would have, in the aftershocks from Sarah, depressed him. Now he texted her with confidence: “I’ve been waiting 30 minutes for you. I’m about to leave.” Two minutes later, she called, brimming with apologies. She was on a break from her job at Car Max and invited him to her place. He went, and after a few minutes of conversation, and a couple of joints for her, they had sex. He was gone in an hour, paying her $300.

That power works the other way as well, with the decision to abstain. “Most clients do expect sex,” writes one sugar baby, “but I’m quick to shut it down. If they disagree, then I move on. I’ve turned down thousands of dollars to hold my ground of no sex. The key is to have them work for you, not for you to work for them. You’re the boss.” John feels just as fond of the women he hasn’t sleep with. He stays in touch with a number of them for nothing more than friendship. Some ask him for advice on business, careers, or college. He usually obliges.

After two years of the sugar lifestyle, John has settled down. It is no longer a numbers game. He is more selective, talking to women more before meeting them, learning more of their personalities. Sex with nine women in one week used to fill him with pride — a meat-eating, Pleistocene pride, but pride nonetheless. Now he prefers quality over quantity. You might ask what’s wrong with John that he prefers sugar dating to traditional dating when he has money and is fun and good-looking. This is like asking what’s wrong with a woman who isn’t married or doesn’t want children. We have a hard time accepting anything that doesn’t follow a social script. John still stings from Sarah, and he views sugar dating as a buffer against further pain. I guess I can’t begrudge him that.

But dating a former Playboy bunny? Dude. Not cool. Unless she brings a friend for me.

Writer. Editor ( Librarian. Lover of books, cats, and comic cons. Hater of vegetables. Tweet: @anthonycaycock

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