Meet the Sugar Daddies Who Are Actual Fathers

Chris doesn’t need anyone to tell him he’s a good dad; he knows he is. But a lot of people do tell him that, because it surprises them.

It surprises them because he’s gone a lot. He travels frequently — sometimes for work and sometimes for “work,” usually for a little of both. He favors Fort Lauderdale, where, truth be told, he spends as much time as he possibly can, but other nights will find him closer to his home in the nice part of Connecticut but still not quite there, at trendy hotels in Boston or New York or sprawling suites in the towering, glittery resorts at the Connecticut casinos. And when he’s not home, he’s usually not alone.

It’s the women who accompany him that are surprised to find out he’s a good dad — that when he’s not cheating on his wife with younger women he met on a sugar dating website, he’s carting his oldest daughter around to college tours, doctors’ appointments or helping her write an admissions essay for the Common App. When Chris is around, he’s present. He’s not just footing the parental bills — though he does that too, of course; he pays for the house and the college tuition and the cars on 16th birthdays. “Someday I hope you will understand that all of my business travel and nights out made me a lot of money so that you could go to any college,” he once texted his oldest daughter.

But he’s actually invested in his daughters’ lives, and not just financially. There are two of them, one currently enrolled in the pricey college of her choice, and one who just started high school. He goes to the field hockey games when he can. When a boy flirted with his older daughter who was working coat check at an event one night, she texted her dad about it, complete with a flutter of heart emojis.

Neither one of his daughters suspects a thing, nor does his wife, according to Chris. For someone who plays it rather fast and loose — like that time he dated a senior at the college where his daughter was about to matriculate in the fall — he manages to keep it all highly compartmentalized, even when it seems like he’s getting sloppy. He’s been doing this for years, after all, since well before his daughters could have ever suspected anything. In the early days, back before the internet had a readily available platform for this kind of thing, Chris surrounded himself with strippers and flight attendants he picked up on business trips. Today, at 51, he still maintains an active rotation of young women, most of whom he meets online. You wouldn’t call it steady, there’s a lot of turnover, but there’s never a vacant spot for long. Chris’s life — his second life — is like a merry-go-round, and he’s the carousel barker.

For a long time, the women on Chris’s carousel were older than his oldest daughter. Now some of them are around the same age, which gets riskier, though he isn’t particularly concerned. When you’ve been living a dual life for this long, the idea of those lives colliding seems like an impossibility so completely removed from reality that even if it did happen, it would be happening to someone else, not you. Someday the women he dates will be younger than his oldest, then someday, presumably, even younger than his youngest. What’s that joke about high school girls? They stay the same age? Chris has never dated high school girls, of course — except for that one time, and anyway nothing happened. He was able to piece it all together — the JV soccer photos, the lack of any college graduation year in her social media profiles — before anything could.

If you ask Chris whether he ever worries his daughters might someday bump into him on that very same sugar dating site, he’ll brush it off. Maybe it’s because Chris has little reason to worry about anything. After all, he’s got just about everything: the wife and the 2.5 kids and the house in Connecticut, and the never-ending rotation of young women who magically stay the same age. Besides, why would girls who grew up with a father like him have any need to fuck someone else’s?

Milo, who is the same age as Chris, never worries about running into his own daughter on a sugar dating site because she is only five years old. Milo is on the older side to have a daughter this young, but he doesn’t look it. Technically, he’s old enough to be his sugar baby’s father, but by that same metric his sugar baby is old enough to be the mother of his child, so you don’t notice it so much. He’s still a few years younger than his sugar baby’s actual dad, anyway, who was 32 when his youngest daughter was born and nearly passed out when it happened. Her dad still talks about the smell sometimes. Apparently the miracle of life smells so bad it can knock a grown man to the floor.

Like his Instagram, which is flooded with photos of his daughter but none of her mother, Milo’s apartment looks like the apartment of a single dad. Up until a few months ago, however, it was the apartment of a family with a small child. Still in the midst of a messy divorce, Milo turned to sugar dating for the same reason many people do — not because he believes he “has to pay for it,” nor even because he’s particularly inclined towards displays of munificence, but because the non-traditional context of an arrangement provides a reprieve from the traditional dating script that has failed him twice before: first comes love, then comes doomed marriage number three. For someone like Milo, who is still reeling from his ex-wife’s infidelity and trying to negotiate a second divorce, leaving a few hundred dollars on the nightstand for the woman he sees every week or so buys him more than sex: it buys him freedom from the strings that inevitably if invisibly control even the most seemingly casual of relationships.

In his bedroom there is a bunk bed filled with stuffed animals, and a dollhouse where Barbies in various states of undress sit in naked nonchalance at kitchen tables or lounge on plastic recliners. A set of smaller drawers beside his own are labeled in a child’s scrawl: “Shirts,” “Bottoms,” “Dresses,” “Underwear.” One night Milo got drunk and had sex with his sugar baby on the top bunk of his daughter’s bed, throwing two oversized stuffed animals to the floor below.

A few months ago, Milo’s sugar baby received a call from her father, the one who was knocked unconscious by her birth. He wanted to let her know he’d received an anonymous letter from the wife of one of her sugar daddies, a woman who wanted very much to know why his daughter was having sex with her husband for money. He didn’t have an answer for the woman, because this was news to him, too.

The letter couldn’t have been from Milo’s ex, he knows that for sure, which is why he has room for sympathy — not for his sugar baby, but for her father. He says he “feels really bad” for her dad, either because he imagines himself on the receiving end of such a letter in 20 years, or because he can’t.

Anthony, a 50-year-old newcomer to sugar dating, is not very much in the habit of feeling sorry for other people’s dads, because he’s busy trying not to become his own, who left when Anthony was still a baby. Raised by a single mother and their grandmother, Anthony and his older brother spent a few years in public housing before moving to a tiny apartment in Queens, where they sprayed Raid on a G.I. Joe Terror Dome to craft a makeshift roach trap and made basketball hoops out of wire coat hangers.

But Anthony always loved money, even before he had it. From a young age, he worked as many odd jobs as he could get his hands on. One summer he made $27 mowing lawns. His mother watched him count the bills over and over again.

Now Anthony has real money, the kind you can use to buy yourself two Porsches, in white and black, as a divorce present. Across the span of two marriages, Anthony has managed to accumulate a brood of six, including two stepchildren from his second marriage which, like his first, recently ended in divorce. He may be new to sugar dating, but it comes naturally to him, as the kind of “old-school guy” who, as he puts it, just wants “to make a woman feel special.”

“Being raised by two women shaped me in many ways,” he says. “I recognized the sacrifices they made to raise my brother and me.” When he was old enough, he says, he spent whatever money he had on flowers, cards and candy for his mother and grandmother on birthdays and Valentine’s Day. “I did whatever I could to take care of them the way they took care of me. I always held onto that desire to make a woman feel special. I never wanted to be the man my father was.”

Besides, the way he sees it, in spoiling a young woman on his arm, he’s really spoiling himself. Weeknights with the kids you’ll find him at Chili’s or Applebees out on Long Island, a humble dining experience with which his children are more than content. Having grown up with enough, they never developed their father’s lust for excess, which Anthony sometimes interprets as a lack of appreciation for the things he would’ve killed for — or at least mowed countless lawns for — as a kid. When Anthony bought the family a lake house in Pennsylvania, the kids never wanted to go and complained the whole time they were there. As children, Anthony and his brother spent their summer vacations making candles in Colonial Williamsburg. It’s probably just as well, anyway. Anthony is often torn between wanting his children to have the best, far better than he ever dreamed of, and keeping them humble, appreciative. Like most parents, he wants them to have more than he had — he wants them to have everything — but he doesn’t want them to be spoiled, per se.

But on weekends with a sugar baby, a woman whose humility it is not his responsibility to keep intact, Anthony hires a limo and makes reservations at Ocean Prime. Afterwards he sends roses by the dozens. It’s as much about impressing and spoiling his date as it is indulging his own long-starved lust for extravagance.

“I don’t normally spoil myself,” he says. “But this is a new beginning.”

Names have been changed