Let’s start with the sex. That’s what they’ve been talking about all night, first in the restaurant and then in the condo perched high over the glittering lights of Atlanta. Jodie gets things started. “What time is it, guys?” Eleven p.m.

“It is so late!”

She has a philosophy final tomorrow on Meditations of René Descartes, which she pronounces Dez-car-tez.

Jodie is 20, or maybe she’s 18, depending on which version of the story you get. She has a supertight athlete’s body and a striking face with tiny blue eyes. She’s studying premed at a nearby college, hoping for a career in sports medicine. Kelly admits to 36 or 38, and like Jodie she is blonde but with the coarser beauty of Ellen Barkin. She’s a former computer executive turned real estate mini-mogul. Then there’s Jim, a retired banker who is 56 and amiable looking, still in possession of all his hair and not exactly svelte. Fat, in fact. “Jodie,” he asks, “what’s your schedule tonight? Do you need to—”

She does have a philosophy final tomorrow. He doesn’t want her feeling any pressure.

“No, no, no, no,” she says. She wants to stay. “But I have to get up early.”

So Jim pours more wine and says, “Enough small talk. Let’s go to bed.” But Kelly says she feels sweaty, so she and Jodie are going to take a shower together. “Why don’t you put on some porn,” Kelly says.

Porn. This is the fate of a man with two hot blondes who are definitely going to fuck him. So he puts on a video and strips off his clothes, and eventually Jodie and Kelly come back and start kissing and messing around, and finally Jim gets himself in there, playing with both of them a little and kissing Kelly, and then Jodie starts kissing Jim and the girls go down on each other and get the toys out, the vibrators. Jim puts on a condom because he always uses a condom with Jodie, then fucks her doggy style because that’s how she prefers him to do her. And when the right moment arrives, he takes the condom off and finishes inside Kelly, because she happens to be his wife. Then Jodie puts on her plaid flannel jammies and buckles down to do her homework.

Everyone’s happy: a man, his wife and their college-age girlfriend, who is definitely being compensated in a manner commensurate with her abilities. Or in SD/SB lingo, a sugar daddy, a sugar mama and their beautiful sugar baby. No jealousy, no lingering questions—except those pertaining to Meditations of Dez-car-tez.

Fortunately for Jim, Kelly and Jodie, we live in a revolutionary time when the internet has turbocharged the ancient concept of concubines and courtesans. There exists today a subculture of sugar daddies and sugar babies, complete with their own web-based meeting grounds and notions of morality. The basic tenet of sugar culture: There are wealthy men (and sometimes women) who love beauty and sex, and there are beautiful young women with a special feeling for older men willing to pay their college tuition or mortgage. It’s as simple as supply and demand as defined by economist Adam Smith.

The visionary entrepreneur who got this rolling was a guy named Brandon Wade, an extremely nerdy MIT software engineer who found himself in deep romantic pain as the 21st century began. Remembering the advice of his mother, who always told him he’d have more success with women if he worked hard and could afford to be “generous,” he noticed some sugar-daddy groups cropping up on Yahoo and decided to start a site of his own. His timing was brilliant. Two years after launching SeekingArrangement.com in 2006—in the midst of TV shows such as Millionaire Matchmaker and The Bachelor introducing mainstream America to the idea of attractive women competing for wealthy geeks—the financial crisis drove tens of thousands of young women to the website, looking for “arrangements” with wealthy men.

Today scores of other websites have jumped into the game, but Wade’s remains on top, with more than 250,000 active monthly members—30,000 sugar daddies and about 220,000 sugar babies. Sugar culture has caught mainstream attention; it has been covered by CNN, The Wall Street Journal, Dr. Phil, New York magazine, The New York Times and the Huffington Post. The headline in U.S. News & World Report even found a microeconomic angle—SUGAR DADDY DATING: A VERY PERSONAL STIMULUS. As Wade expands his multimillion-dollar empire, he is hosting sugar parties in posh hotels and launching new websites, including SeekingMillionaire.com and MissTravel.com.

“In the past, you had to be quite wealthy,” he says. “Now you just have to make six figures and have enough left over for a lavish dinner and a weekend trip.”

All of this beams an X-ray through the vexing question of money and its relationship to sex. As Jim puts it, when you grow up rich, you learn there’s a financial aspect to every relationship. “The only difference is that in sugar relationships,” he explains, “the negotiation occurs up front.”

Jim is a pillar of his community; only his closest confidants know of his taste for sugar, which is fine by him.

“I’ve got it pretty good,” Jim says. “I can’t complain.”

“Yeah, you got a pretty good lifestyle,” his sugar baby, Jodie, says.

“It’s not bad,” his wife, Kelly, says.

“It’s not bad,” Jodie says.

“It’s not bad,” Jim agrees.

Fun is the operative word. Jodie loves it when they pull up to a restaurant in the Rolls. The door pops open, she says, and out comes sugar mama Hot Kelly with her long legs. Then the seat flips down and out comes sugar baby Jodie. And the valets go nuts.

Kelly laughs. “See, I like her because she always refers to me as Hot Kelly. This girl is better than a Brazilian butt lift. She makes me feel like a million bucks.”

“I love it,” Jodie says.

“I love it,” Kelly says.

“I get off on it,” Jodie says.

“I get off on it,” Kelly says.

Jim sits there like a pasha on his throne. Yes, he gets off on it too. He explains: “If I walk into a popular bar in Atlanta as a normal person, there are going to be 10 or 20 gorgeous women there. What chance do I stand to attract them? None. In the normal world, they’re in short supply. But in the sugar-daddy world, how many multimillionaires are there who are looking for those girls? One or two. So for one multimillionaire there are 10 or 20 beautiful girls.” He smiles. “I’m in short supply.”

How did Jodie, a college student who had a “strict, strict, strict” upbringing, arrive at this place?

Jodie grew up in the suburbs of Boston, the daughter of a computer programmer who stayed on Jodie’s back all the time about making good grades. Her dating life was limited to a single boy who had to submit to an old-fashioned paternal interrogation. “My family’s like, ‘You need to find one and just stick with him and that’s it,’?” Jodie says. When her parents told her they couldn’t afford another year of college, she knew she’d have to get a job to help pay for tuition. Jodie takes her premed studies seriously.

Shortly afterward, she met a girl who had a sugar daddy. The girl said all she did was walk around in her underwear and read books to a rich guy, and Jodie couldn’t help thinking, God, that sounds so nice; maybe I’ll find some really old guy and read him books in my underwear. When she got home, she went straight to Google and typed, “Where can I find a sugar daddy?”

She found the Seeking Arrangement website. It can’t hurt to sign up, Jodie told herself. It would be her secret, a dirty little secret nobody would guess in a million years, so glamorous and…bad.

She says her friends joke, “‘I wish I had a sugar daddy,’” and she thinks to herself, Ha-ha, I do have one.

“And a sugar mommy too,” Kelly adds.

Jim and Kelly pay her tuition, from $3,000 to $5,000 a month.

Jodie says she loves the secret life. “Everybody wants to know what I do. Like, ‘Where does Jodie go? Where is she sneaking off to? Why is Jodie talking about the Opus One she drank last night? Where did Jodie get that Lilly Pulitzer dress?’ “And they’ll never know,” Jodie says. “It’s my little secret.”

The secrecy is especially delicious because Jodie belongs to a sorority where Lilly Pulitzer dresses are the thing, and she could never afford one on her own. So Kelly took her shopping and bought her a Lilly dress, and when she got back, her sisters just died. How did Jodie get a Lilly dress? She was so thrilled she sent Kelly a text message: “You turned me into a Lilly whore!”

Kelly smiles, almost like a proud mother. “Her first Lilly dress.”

Their initial meeting was on Skype. Jodie had sent Jim and Kelly a note through SeekingArrangement.com because their profile seemed normal and safe and especially because Kelly had once been a sugar baby on Seeking Arrangement herself. She wasn’t some wife who was pissed off because she had to do this to save her marriage. And Jodie liked how honest Jim was. From the beginning he said, “Here’s my name; google me. You know I come from a semifamous family, and you’ll see my pictures and all the committees and boards I’ve served on.”

Kelly teases Jodie for showing up for that first Skype call directly after a workout, hair still sweaty. “It’s all slicked back and greasy and she has this sports-bra uniboob going on,” Kelly says. “She’s like, ‘Yeah, I just got back from the gym. Do you think I’m hot?’ Jim’s like, ‘Oh my God, I don’t know. She looks a little too—’?”

“Sporty,” Jodie supplies with a giggle.

Flat-chested would be another word. Jim likes curvy, but Kelly liked her.

“I’m not attracted to somebody my age,” Kelly says. “It’s a fantasy for me—I don’t want to fuck myself. I wanna be with some hot young thing. That’s my fantasy.”

After the Skype meeting, they met at a hotel near Jodie’s college. Jim and Kelly seemed so normal. They were a family, raising a child together. Other than that, it was just like any other blind date. They ordered wine. They ordered dinner. Kelly gave Jodie advice on how to avoid creeps and how to cut her meat.

Jodie had a million questions. What do you guys do in bed? How many sugar babies do you have at once? How many have you had? Am I going to be hanging out with other girls?

Kelly laughs, remembering the evening. “Oh, if only Jim was 18 again.” She turns to Jim. “I don’t think you can handle yourself in a large group.”

He laughs. “In my dreams.”

She also teases him about wearing plaid. “All you need is the pocket protector and you’d be all set, babe.”

Jodie joins in. “It’s best when he pairs it with the short shorts and the high socks.”

Jim takes the abuse as gracefully as he carries his big gut, confident in his manliness.

The arrangement is especially nice, Jodie says, because Jim and Kelly don’t care if she dates other people. Instead they say, “Tell us about it.” Like this guy Jodie dated who was 36. Kelly said he was too old but not old enough.

“Young and hot or old and wealthy,” Kelly explains. “I mean, really, there’s no in-between.”

Jim’s pied-à-terre is on a high floor of a building right in the heart of Atlanta’s Buckhead district. As Jim finds a suitable wine, the conversation steers to Kelly. How did she end up a sugar mama?

Kelly grew up a math nerd in Connecticut with strict Catholic parents who had sex only three times to produce each of their three children. Or at least that’s Kelly’s theory. Her dad was an engineer, her mom a school administrator. Both were very frugal. College was paid for, but she never had a designer dress. That was wasteful. What’s wrong with JCPenney?

Sex was Kelly’s rebellion. She had three-ways in college. She went to sex clubs. Most of all, she fantasized about being a geisha. One night a rich boyfriend gave her a roll of bills and told her to buy a new bed for them to fuck in. “Like, that was just hot for me.” Next time, he gave her $500 to buy a bottle of wine. “Think of me when you drink it,” he said.

But the pull of convention was too strong. Kelly graduated from a respected college and went to work for a legendary computer company. She married an age-and income-appropriate guy and paid her mortgage six months in advance—until the day when she became fed up with her husband’s drinking problem. After the divorce, she went looking for a man who would treat her the way her rich boyfriend had.

“Even though I was making a lot of money, I was banking it,” she explains. And if a rich boyfriend offered her money? “I’m still making Mom and Dad happy,” she says, “because I can use his money to get that designer dress. I can use his money to get Jimmy Choo shoes.”

Now Kelly is like a missionary for the sugar lifestyle. She sees the college boy with his shirt open showing off his abs and thinks nothing at all. But an older guy with a briefcase and a hint of gray? Hot. With summer break coming, she’s even planning to fly Jodie to the coast to introduce her to a distinguished older gentleman (we’ll call him the Executive). This is because sugar relationships have a shelf life of about six months, says Kelly. Then it’s often on to the next thing for all involved.

After all, Jodie’s used to the lifestyle now. “It’s like a special thing,” Jodie says. “Pretty much helping me out.” Jodie is very happy to get Kelly’s advice. “Kelly knows everything in this industry,” she says.

Kelly’s eyebrows go up. “Industry?”

“I mean lifestyle,” Jodie says. “I don’t even know what to call it. She knows what she’s talking about. I mean, they even go so far as to tell me, ‘Do not cut up all your meat before you eat it. Cut it one slice at a time.’?”

“Yeah, I’m teaching her: Put your napkin in your lap; don’t suck down your wine in one gulp.… I’m teaching her, like, 10 years’ worth of knowledge in one month,” Kelly says.

This is fundamental to the sugar experience, Jim says. “When you read some of the traditional literature about sugar daddy–sugar baby relationships, one of the big attractions for young women is the mentoring aspect. That sounds trite until you experience it. It is actually one of the more valuable parts of the relationship to the young lady. And it’s fun for us too.”

Of course, the lessons extend to sex. They don’t go into detail about this, but Jim gives a hint in a smile that speaks of satisfaction with a solemn responsibility properly discharged. “I can tell you, the next guy she meets is going to be much happier than the last guy she dated,” he says.

“I tell her things that maybe her mother should but would never,” Kelly says.

“We just don’t have, like, boundaries,” Jodie says. “I mean, in the eyes of society we’re all sinners; we’ve all just thrown our morals out the window. So everything’s just out on the table.”

Back in Boston, Jodie has a serious boyfriend who wants to marry her. She doesn’t feel she’s cheating, because they have a no-tell rule while she’s at school. But it would be the end if he ever found out. At the same time, she feels really close to Kelly and Jim. “Hopefully when I’m married and I’m older,” she says, “I’ll still keep in touch with you guys.”

At lunch the next day Jim finally gets a chance to tell his own story. He grew up relatively middle-class, he says.

“Jim’s version of middle-class is my version of upper-class,” Kelly says.

“We lived in a very middle-class house.”

“You lived in the nicest neighborhood in town.”

“No, no, no, we didn’t, actually.”

“He’s lying.”

Jim rolls his eyes. “Anyway, I was middle-class my whole life, but I was very happy.”

He ended up making millions in banking and marrying a beautiful woman who didn’t much care for sex. They had kids. She got depressed. Life turned gray. Counseling failed. Finally Jim felt he had two choices. “I could stay in the marriage and be miserable, or get a divorce, which I didn’t want to do for the kids,” he says.

A third choice occurred to him, but his wife caught him and initiated divorce proceedings.

Free at last, he was ready to fulfill his fantasies. A friend advised him to play the field, but Jim quickly found that a 50-year-old man with a taste for plaid was something less than a sex magnet. He went back to his helpful friend.

“Well, the first thing is you’re driving a Ford Taurus,” his friend said. “Go buy a nice car.”

Ridiculous, Jim insisted. Women aren’t that shallow. They’ll see through that right away.

But he tried it. “What I found is if I picked a woman up in a Rolls and was wearing a nice suit, I was going to get laid.” Fancy cars and expensive clothes were the male version of big boobs.

Then he discovered Sugar Daddy 101, a guidebook that turned his insight into an entire philosophy of modern, eyes-open intimate relationships. There was a price on everything, it argued, and wise women learned what it was. From the book he found his way to the Seeking Arrangement website, which certifies the assets of its sugar daddies and sugar couples so potential sugar babies know what they’re getting into.

Jim got certified to $10 million and began to experiment. He became obsessed with beauty, and, man, was it a rush. But like all rushes it faded, and he found himself stuck with too many vacuous beauties. So he started focusing on personality.

This led to an unexpected pleasure when one young woman he dated, someone he genuinely liked, admitted that she’d gotten deep into money problems that even Jim’s monthly sweetener couldn’t resolve. He got out his calculator and spreadsheets and helped her restructure her finances. After that, mentoring became a large part of his pleasure in the sugar lifestyle. “I really do feel like I’m making a positive contribution to society and to these girls in particular,” he says.

Jim and Kelly insist there’s a difference between a college girl paying her tuition and a full-time sex worker paying her rent. “Because then it becomes prostitution,” Jim says. (Alas, the cop who answered the phone at the Atlanta Police Department snorted in derision at this notion. “You can’t pay for sex for any monetary gain,” he said.)

“The idea that someone I’m going to be with has been with five guys already, that’s just gross to me,” Kelly says.

“We’re in a difficult position to be judging anyone,” Jim says, “but that’s not attractive. It’s just not attractive.”

“I’m very much a feminist,” Kelly says. “I think women should support themselves, not rely on a guy.”

And what about the idea that for someone as young as Jodie, being a sugar baby might be a formative experience that will warp her life?

“She was on the website already,” Kelly says. “We didn’t go drag her on the website.”

In Jim’s mind, that’s one more reason to like college girls. They’re smart enough to make thoughtful decisions. Jodie knows what she wants from life and is taking pragmatic steps to achieve it. Jim admires that. “If she thought we were taking advantage of her,” he says, “she wouldn’t be doing this.”

Let’s get a little more comfortable, shall we? Into the Rolls! Oh, how beautifully money expresses itself in stitched-leather seats and a hammered-aluminum dashboard. “Nothing bad ever happens in a Rolls-Royce,” says Jodie.

An hour’s drive brings us to Jim and Kelly’s gorgeous home in an Atlanta suburb. There’s a sitting room with a family portrait, a dining room centered around an antique mahogany table, four large bedrooms and a magnificent kitchen: elegant yet homey.

Kelly’s daughter’s room is an explosion of pink with castles and butterflies but no TV. Except for prescreened Disney movies, Jennifer has never watched TV. “I don’t want her to watch commercials and say commercial things and want things,” Kelly says.

Soon Jennifer comes home from school, a Hummel figurine in a white shirt and black skirt, her straight hair pulled back with a black headband. Kelly asks what she learned in school.


“Nothing? I want to talk to your teacher!”

At dinner, Vivaldi plays as Jim talks about his kids from his first marriage, how they’re sending out résumés, looking for jobs, how tough things are now. The housekeeper sits with them. Then Kelly takes Jennifer off to bed and Jim sits down to explore the latest offerings from Seeking Arrangement. Since these relationships tend to fade out and Kelly wants a date night once a week, Jim does a little bit of this every day. Right now he’s looking for Jodie’s summer replacement. His in-box has 182 messages.

“Oh, it’s just never-ending,” he says. “We get four or five e-mails a day, on the weekends 20 or 30 a day. There’s no way you could meet all these girls.”

Here’s a 20-year-old hardbody from Turks and Caicos. “Hi, I am a young pretty sweetheart and would love to meet someone older, confident and kind.”

Jim likes her body, but she’s not educated.

Here’s Nikki, a 21-year-old from New Jersey who specifically requests a sugar couple. That’s unusual, though less unusual than it used to be. And she’s a college student who says she’s been through tough times, which is good because she’s being honest. Jim cuts and pastes one of his prewritten responses: “Hi, I’m Jim, an old-school Southern gentleman.…” Here’s a prospect from San Francisco with an amazing body. “I’m a lusty, petite and curvy woman of passion and pleasure,” she begins.

She’s overselling. Jim deletes her.

When Kelly comes in, the delete rate soars. First to go is a 28-year-old who says she wants no less than $20,000 a month. “This is crazy talk,” Kelly says. “I wouldn’t even give this girl the time of day.”

Here’s Taylor, a beauty from a small town in Alabama who “has some stresses a pretty girl shouldn’t have to fret over.”

“She’s a little chunky,” Kelly says. She stops at a young blonde. “She looks hot. I go for blondes. How old is she?”

Twenty-six. Which means she’s probably 32, Kelly says.


A professional musician strikes Jim as the perfect girl next door. Kelly disagrees. “I think this girl is a man.”

The next one’s willing to relocate. “This girl needs a place to live,” Kelly says.

Should Kelly be a little more sensitive? Is it weird for a woman who calls herself a feminist to judge her sisters so harshly?

“We just have our pick,” says Kelly. “It sounds wrong and it’s not very feminist, but it’s a fact of life. And as the recession gets worse, it gets better.”

Finally they find a prospect who looks as though she walked out of a Victoria’s Secret catalog. “If that’s really her,” Kelly says, “she’s hot.”

Jim scans the profile. “Look, there’s a comma after ‘whoever.’ And there’s an ellipsis, and it’s actually in the correct place. She can punctuate!”

“This one will never go for us,” Kelly says. “She’s gorgeous, she’s smart, she writes coherent sentences. She’ll be going for a billionaire.”

This is where Jim takes over. “We’ll find out,” he says, executing a quick cut-and-paste, sending a blast of desire along with the hydraulic whoosh of outgoing e-mail: “Hi, I’m Jim, an old-school Southern gentleman.…”

In the morning Kelly comes down to the kitchen in a pair of pink Hello Kitty pajamas. Slicing strawberries for Jennifer’s cereal, she announces her plans. “Mama’s going to be gone tonight.”

“That’s twice this week,” Jennifer says.

“I’ll be back.”

“I don’t know if you will,” Jennifer says.

“When do I not deliver on what I say? Your mom’s a rock. If I say something, it happens. You don’t have one of those flaky moms. The only thing that could keep me from making your soccer game is if there’s a delay in flights, which I can’t control.” After good-bye kisses, Kelly heads out in the Navigator to pick up Jodie; today they’re flying to the coast so Kelly can introduce Jodie to the Executive. This will probably lead to a three-way, which would be Kelly’s first three-way without Jim since they got engaged.

On the way, she tells her version of their story. She met Jim on Seeking Arrangement five years ago. At first she dated other sugar daddies, and Jim had other sugar babies. It was just fun, and Jim’s secret kink tickled her fantasy. “The idea that my dorky boyfriend was banging these hot girls with huge tits,” she says, “that turned me on.”

Gradually it became clear there was serious potential in the relationship. They clicked. Kelly is fire and Jim is earth, Kelly the hard-charger and Jim the quiet force who keeps everything in balance. Even their relatives thought so. Her mother told Jim, “Usually Kelly runs right over men, but you know when to shut her down.”

So Jim got serious about Kelly. How serious? As serious as the $150,000 Tiffany diamond that now glitters on her left hand. Serious enough to give up sugar and commit to a normal life as a normal couple.

But when Kelly finally felt secure, finally felt sure she could trust Jim, she said, “I kind of miss the lifestyle, don’t you?”

Enter sugar babies and, eventually, Jodie.

As Kelly gets closer to the college to pick up Jodie, she begins to get nervous. “Isn’t it weird?” she says. “I’m picking up my girlfriend at her dorm.”

Jodie comes out with her bag and some homework. “I’m going to be really lame on this plane and work on a paper,” she says.

She’s wearing a perfume called Victoria’s Secret Bombshell. She also has a bottle of Chanel Mademoiselle. “One is my sexy scent, and one is my fun, flirty scent.”

That’s good, Kelly says, because “happy and fun” is the theme of the weekend. The Executive doesn’t like drama.

At the airport Kelly gets disoriented in the parking lot and can’t figure out where the terminal is. The momentary lack of control visibly upsets her. “Where the freak is the terminal?”

“It says Delta right there,” Jodie says patiently.

The truth is, Kelly is nervous. A threesome? Without Jim? She and Jim came up with the idea over a bottle of wine and it sounded fun, but now it seems wrong. The Executive is richer than Jim and fitter too. Jim doesn’t say anything, but she knows it bothers him. I’m not a sugar baby anymore, she thinks.

Maybe she’ll just do stuff with Jodie.

In the meantime, a sugar mama has her responsibilities. Where was she? “The Executive is not married, he has two grown children.…”

Jodie thinks he’s handsome, but clearly he has had work done. Kelly laughs. Jodie says, “You think I don’t know what plastic surgery looks like?”

“And that’s the reason the Executive is a perfect choice for Jodie,” Kelly says, “because Jodie wants to get her boobs done.”

Really? A beautiful girl like her?

“I stunted my growth in gymnastics,” Jodie says. “Four hours a day, including Saturday and Sunday. I didn’t hit puberty until I was, like, 16.”

Kelly’s eyes narrow. She turns her focus on Jodie. “Can you, like, do the splits?”

“Yeah. Maybe. I haven’t tried in a while.”

Perhaps it’s the slight flaring of her nostrils or a sudden flush to her skin, but somehow Kelly gives off a flash of sexual heat that could light up an airport terminal. “I’d like to see that,” she says.

“I’ll try,” Jodie says.

And off they go, bad and beautiful in their Lilly Pulitzers and Jimmy Choos, chasing glamour and moonlight and money while Jim surfs the web at home, waiting patiently for another chance to raid the sugar bowl.