
on a wintry New York evening in February. A driving, icy rain shivered off the backseat windows of our aging Chevrolet taxi as we wound through the grid of Manhattan streets. It had been a long ride — a circuitous, backtracking, intentionally time-stalling journey. I had planned it that way, slipping the driver a twenty and telling him to take his time getting uptown, where each of us lived. She and I were cozy inside, curled into a joined bundle of two overcoats, slouched low in the backseat. Tonight was our first date, and it was going nicely, better than I had expected. As the car idled in front of my building, she stared at me, a little tense. I stared back. The sexual momentum was rolling forward implacably, and the only logical conclusion lay across the icy sidewalk and up five flights of stairs illuminated by sickly blue-white halos of fluorescent light. That's where my apartment lay, the top floor of a battered tenement on Manhattan's otherwise posh Upper East Side. "Well . . . " she said, open to possibility, a little confused by my hesitation. I stole a glance down at her trim black Agnès B. wool sweater. Her weekly budget for stockings — maybe three sets of twenty dollar Calvin Kleins — equaled my seven-day outlay for groceries. I handed her another ten for her ride, kissed her right on the forehead beneath her Frederick Fekkai-coiffed bangs, then bid her a hasty goodnight. I could not afford this. I could not afford her. I was twenty-six then, trying to patch together a coherent New York life on blind ambition, Food Emporium pasta coupons and the twenty thousand dollars afforded by a low-level job at a glossy magazine. The woman was a Seven Sisters graduate from a good Westchester County family. It took only a deep, clove-y noseful of her Aveda shampoo to remind me, at that moment, that she had a certain life and certain expectations that were simply beyond me, at least at that point. I told her I was spent. I think she thought I had cooled on her. But I had simply, if subconsciously, put her — and to some extent, my sex life in general — on hold for a bit, until such a time that I could afford a life that included her and a better-looking apartment to take her to. Eight years have passed since then. In retrospect, I'm ashamed to admit that I ever let money have that much power over me. It seems so paranoid, so cynical, so cowardly. I'm more financially secure now, which makes the matter less pressing, in any case. But I like to think that I've abandoned those kinds of calculations, that they're relics of my early adult naïveté, my career adolescence. Of course, in reality I'm still susceptible to those insecurities. I've begun to forgive myself for them, given the era in which I've built my career. As I was struggling to bury those old money neuroses, the world kept shifting, the stakes kept getting higher. At one point before the Nasdaq slide last year, the leafy college town of Palo Alto, about two miles from where I grew up, was minting sixty-four new millionaires a day. Wall Street, the New York Post tells me, has doubled its total number of millionaires in this first year of the new millennium, as of the bonus season last fall. Money concerns may be eternal, but the numbers defining financial success have ratcheted higher, like a moving target heading relentlessly north. Some people no doubt have a sexual set point that no amount of money or power will influence — they have either an unshakable level of self-assurance or a lack of confidence impervious to change of fortune. But for the men and women who don't fall into either of those categories, this social sexual experiment known as the '90s Boom has allowed them an unprecedented opportunity to buy the promise of transformation. Some are a little drunk with money, using cash as a lubricant to slide open the cage that once constrained their jostling Id. Money becomes a means to purchase a newly polished sexual self as just one more lifestyle accessory. And for many of us watching that happen, it can feel like a zero-sum game — as the high rollers' confidence rises, ours correspondingly drops, so that no one is left altogether untouched. I do know people unphased by their money — a couple of my friends from high school graduated from college, married happily, became millionaires, have nicer-than-average homes and go on nicer than average family vacations. But they're not the ones who pique my curiosity, who make me periodically obsess over the what-ifs of another career, another stock portfolio. With every ten thousand dollar raise, I've felt a surge of entitlement, a notch in my level of confidence that affects the kind of women I pursue and how I pursue them. What would ten million dollars do to me? What would I do with it if I could? of an acquaintance, a decade or so younger than I am, and a perfectly good representative of the moneyed, entitled young generation. He's quietly attractive, in a pre-prison–Robert Downey sort of way. A tech specialist in college, he seems too charming to be a nerd but a little too sweet to be a lady killer. Cameron graduated from Georgetown University two years ago and quickly moved to Austin, Texas, where he accepted a job in software development for a high-tech start-up. His steady college girlfriend intended to follow him out as soon as she graduated the following semester. Cameron had been as faithful as he was conservative, someone who hadn't lost his virginity until his senior year of college. Cameron's salary started at fifty thousand dollars, but it didn't stay there, and when his income rose, "It completely changed my confidence," Cameron tells me. Within a few years, he'd bought himself a new convertible JK8 ("for the weekends"), and an Acura to drive to work. He had a house in the suburbs and a loft downtown, and was pulling in two hundred thousand plus stock options. His relationship fell apart two months after his girlfriend joined him, and Cameron tells me matter-of-factly that it was his own inflated ego — connected to his own inflated income — that doomed the pairing. Names and identifying features have been changed. "I don't want to go so far as to say I started doing spreadsheets on my dates," he says. "But I started looking at women completely differently. Every single piece of furniture I bought, I based it on what I thought the cash return for, like, ass would be. I'd think, 'Damn, that's a twenty-six hundred dollar bed frame. Now twenty-six hundred dollars would be like a night with a good prostitute. I'll get at least one night of sex that good out of that bed frame.' I turned into the classic guy — 'Yeah, she's hot, let's see if I can get her in two hours.' I went to a friend's wedding, and three hours in — this was completely counter to me — I don't even know her name, but I'm in bed with a nineteen-year-old fashion major." Cameron is describing the foibles of a twenty-four-year-old kid, all tittering bravado, but I feel lured in. If Cameron were a brash Wall-Streeter, the kind who'd once hung out on his fraternity porch and rated girls from one to ten, I'd have no problem working up the obligatory contempt. But he's not. He's more like the guy who played second clarinet, and I therefore find his newly found, guiltless, almost Nietszchean hedonism oddly liberating. I almost identify. I also know that Cameron is a rather small fish in the ocean of young, overnight plutocrats. For some time, I've been hearing about the success of another friend of a friend, Thomas, who'd grown up middle class, then made a fortune in finance at a very young age. He was a quiet athlete in high school, shy, not quite 5'5", someone who "was never part of the in crowd," our mutual friend tells me. His financial success "completely changed his approach to women. He became fearless. He'd have no qualms about walking up to a woman in a bar and just propositioning her, not in a sleazy way, but just like, 'Hey, I'm really attracted to you, and I'd really like to spend the night with you.' He basically bought his shame away." Curious, I look him up. He agrees that until securing his job as a commodities trader, he'd never been much of a dater. "I'm a sucker for what is told to me, and growing up you're taught that sleeping around isn't good," he says simply. Thomas has the self-effacing friendliness of someone who'd strike up a conversation if you were both at a bar watching a football game. He tells me that things began to change in his sex life when the money started rolling in. His salary rocketed from forty thousand to one hundred thousand to eight hundred thousand. Then, he shrugs, "I sort of took a leap." Thomas transferred to a top job in Paris, and was soon pulling down more than two million dollars a year. In the summer, he'd rent a house in St. Tropez for fifty thousand dollars a month. "In Paris, I started going out to nightclubs, and I found myself wanting nothing more than to get laid. That year, I slept with anybody I could. Secretaries in the office. Swedish au pairs," he says. "At one Christmas party, I was drunk, another guy's secretary was drunk. We went home together and had great sex. In my mind, money didn't play into it. But in her mind, I'm sure it did. If I had to put a number to it, how many of these women slept with me because they knew how much money I was making, probably seventy-five percent." Before long, Thomas found that a fling with a quasi-underling was not enough to get him off. "I started throwing big parties at my flat in Paris for 100, 150 people. Each time I threw a party, I slept with somebody new; a person of high quality, too." I'm struck by the phrase: "high quality." It's a term I hear other wealthy men use to refer to their dates, as if the women in their world came objectively graded like ten-year-old bottles of Brunello di Montalcino. And it touches a chord: I've always felt like I have a governing mechanism inside my head that stops me from being attracted to beauty over a certain level. The thing is, I've noticed, that mechanism is adjustable. I've dialed it up as I've attained more success. "These parties," Thomas continues, "were completely decadent. One time I threw a toga party. Basically, a bunch of guys from the office and I said, 'We're working too hard to go out and get laid, and everybody we know is in the exact same boat, so why don't we throw everybody together and solve our problems all at once?'" People came. They brought jello shots. They brought chocolate dildos. Thomas has no illusions about how traditional his sex life would have been had he ended up making forty-five thousand dollars a year in Cleveland. He would have gotten married to a nice girl, stayed faithful (probably) and, for him, Penthouse Forum* would have remained fiction. Some disdain creeps into his description of the lifestyle he's bought into instead: "People were basically running around like fucking retards, throwing the jello at everybody, eating the dildos." The flat never recovered. "It was destroyed," he laughs. "I had chocolate ground into the carpet." He sighs wistfully. "It didn't degenerate as much as you'd hope, with people having sex in the hallways. But a few people slept together. I ended up picking up this woman who I had met a week before at a party. Before that, she wouldn't even talk to me." confidence has indeed burgeoned with financial success, a quality that no doubt grants them an edge in just about every social interaction, from wooing a client over golf to getting some cover girl a Cosmopolitan, fast. But "confidence" strikes me as too weak — too clean — a word for what defines this personality shift. I sense something more predatory, like an adrenaline rush. There's been no shortage of science and quasi-science in the popular press that links this rush to our own hypothalami. Testosterone has become something of a media star of late, gracing the cover of both The New York Times Magazine and Newsweek. This hormone is what makes us boys male, in the biological sense — it literally puts hair on our chest, providing the very signifiers of masculinity. There's plenty of controversy, however, about what this means in terms of behavior: do levels of testosterone alter with life experience (such as work promotions or divorce)? And is the hormone really the source of traditionally "masculine traits" — aggression, risk-taking? Among the more prominent people on the pro side of this argument is James Dabbs, a clinical psychologist at Georgia State University in Atlanta and author of Heroes, Rogues, and Lovers: Testosterone and Behavior. Dabbs posits that aggressive, socially dominant males, whether entrepreneurs or athletes, tend to have naturally higher levels of the hormone. "A high-testosterone male is very straightforward, unconcerned with what others are doing," Dabbs says. "He's less likely to ingratiate himself and smile. He's less afraid to go into a new situation. Generally, he's more fearless. He's not afraid to take a chance, and others can sense this. A testosterone surge makes you intimidating." Dabbs also asserts that high-testosterone males are sexually restless and tend to have more partners. I find this compelling because it confirms the possibility that the very process of making money, as opposed to simply having money, is transformative. Dabbs says that testosterone levels in any man can vary fairly substantially over the course of a lifetime — indeed, over the course of a month. For instance, shortly after marrying, men see a decrease in the hormone. Conversely, recently divorced men, once the inevitable first flush of depression passes, experience a noticeable spike upon re-entering the single life. Testosterone may give us the intensity and strength to overcome adversarial, even life-threatening, moments. The closest most of us come to such moments is in the business world. And what happens in the workplace, according to Dabbs — closing a big deal, cashing in on an IPO — can indeed spike testosterone levels by as much as ten percent, a figure that's significant enough to alter behavior, he says. That's one theory, then: money does make the man. Almost literally. in San Francisco, and although Alison, twenty-eight, and Jennifer, twenty-seven, work in the international sales department of one of the world's best-known Internet companies, they're plenty relaxed. Either sales are slow, or business is so good they can kick back, but either way, they're happy to kill an hour or so on the phone discussing how their newfound wealth has changed their sex lives. The two women, both multi-millionaires since their company went public a few years ago, pass the phone back and forth, giggling about the details they're half-proud, half-embarrassed to admit. Jennifer's theory of the transformation is pretty straightforward: "The money changed my attitude towards relationships, so therefore that changed my sex life." As soon as she "got less needy about marriage," as she puts it, she stopped concerning herself with whether or not her dates would make trustworthy earners and partners and started concentrating instead on how they made her feel. "If you're in a secure position financially, you might be more willing to date someone who's a little more wayward, a little less reliable in many ways, and those kinds of people," she says conclusively, "often tend to give you a more exciting sex life." "Since I came into the money, I've become a lot less interested in stable relationships," agrees Alison. She explains that it would have been logistically difficult anyway to sustain something serious with all the traveling she was doing for work. "I had men in a lot of the different cities I'd go visit — you know, if I'm in Hong Kong, it must be Richard, that kind of thing. 'Richard, you have to come stay with me at the Four Seasons, it's fabulous.'" The money allowed for a balance of distance and convenience that felt right: "If I was dating someone who lived in Europe, I had enough money that I could get on a plane and go see them once or twice a month, or I could fly them over to see me." In the background, Jennifer interjects indignantly, "You let those guys sponge off of you?" "There were those two guys from London I flew over, each of them on multiple occasions," she reminds Jennifer. "Oh, wait, no, there were three — ," and the two of them start laughing. "Hold on, I'd better check my credit card bills." I'm coming to the end of a disquisition from Jennifer on the merits of French men versus their American counterparts when Alison wrests the phone back to tell me her "favorite 'young girl gets rich' story.'" Apparently, a millionairess colleague of hers (she didn't return my call, but her voice mail message sounds steely and mature) has fallen in love with a bank robber fresh out of jail. "She pulls up to this coffee shop every morning in her Land Rover, and that's where he works as part of his rehab or something," Alison tells me conspiratorially. "He's not allowed to date customers, and he's got to do this coffee shop thing for another seven months, but she's already moved the guy into the house in Napa she just bought, the one she paid for all in cash. Literally, the guy robbed something like thirty banks in two years, something outrageous. My friends and I — we're trying to be nice. But you can imagine — we're slightly concerned." She pauses. "I met him, though, and you know what? He is cute." — whatever it is that causes the libidinal leap that goes along with money (let's call it potency), women experience it too. A woman I know once confessed to me that at some point during every high-power monthly meeting with her board of directors, she used to excuse herself to go masturbate in the bathroom. My friend Sally tells me that after closing a major deal she wants to "rip the suits off half the guys in the room and throw them on the conference table." She says that sometimes when a deal's going down, "if it's a roomful of attractive young people and there's this energy in the air, you have the feeling that at any minute the whole thing could degenerate into some kind of an orgy." Sally, thirty, a 5'4" brunet-turned-blond entrepreneur, grew up being carefully coached to marry rich, as her mother had (several times, in fact). Instead she lives with someone several years younger who goes to work at a non-profit in jeans while Sally teeters off to meetings in three-hundred-dollar stilettos. Her relationship predates her three-year-old business, and she says she's seen a change in their sex life that corresponds to her increase in net worth. "Look, I think it's very primitive," she says. "When I come back from closing a big deal, it's like I've vanquished my enemies." She bellows for effect. "It's a rush — you feel more alive." On the one hand, she's exhausted from stress and from long hours; but even still, she thinks since she started making real money she's wanted more sex and initiated it more frequently. "The money makes you more like a man," she says unapologetically. Although the substance of their sexual repertoire hasn't changed, she herself is more abandoned when she's feeling financially flush. "It's being in control," she explains. "It makes you less afraid of losing control." I spoke to six women thirty or under for this story, every one of them worth millions, and not one of them said she'd ever felt a man was intimidated by the extent of her wealth relative to his. "Are you kidding?" said Alison when I posed that question. "There was one guy who was unemployed at the time — if I'd have let him, he'd have come with me on every business trip I had, ordering up room service at the four-star hotels and eating bon-bons while I went to work." If anything, these women have grown remarkably adept at appropriating the standard male techniques of wooing — many of them talked of flying off to Mexico (for some reason, it's always Mexico) with a paramour. But while in men, that approach can seem arrogant, one woman described it in her experience as a gesture inspired by vulnerability. "Twice there have been guys I called up and said, 'Guess what, we're going away for the weekend, I'm paying,'" explains Karen, twenty-nine, a tall Midwestern blonde who's a top executive at a mid-sized New York dot-com. Throughout our conversation, she periodically jumps off the phone to talk heatedly into her cell, which is ringing constantly in the background. "Both times, it was with guys I liked a lot, who I could tell weren't as much into me," she explains. "But I knew they'd say yes if I was paying, and I was right. So they go for their reasons, and I go for my reasons, and that's fine." The most essential difference I noticed between the men and the women I interviewed lies in how they perceive the object of their objectification. The wealthy women have a shrugging acceptance of their dates' motives — namely, to have some fleeting fun on someone else's credit card. Many of the wealthy men, on the other hand, revealed a profound cynicism, an unwavering mistrust of what they suspected their dates were after — namely, a long life of luxury on someone else's credit card. I thought that having no money made me paranoid when I was a young man, but after talking to Ken Carmel, I wondered if poverty might actually be Prozac in comparison with sudden wealth. A mildly successful entrepreneur until his mid-thirties, Ken swept his way through three different dot-coms in the past four years ("I've got around ten million, but you gotta have at least fifty to retire"). Ken is witty, but his humor is darkly confessional, driven by dissatisfaction. He jumps from one subject to another, as if so irritated by the nature of the thing he's discussing, he can't help but move on to the next topic. "If you're honest with yourself," he says, "you realize your money buys you hotter women. Since I made my money, yeah, I've been dating much more beautiful ones. You know, I used to date really funky, artsy, interesting women, just like I used to decorate my apartment for a thousand dollars with funky furniture I would find at the Chelsea flea market. I just don't have time for either of those things anymore. You don't have time to date, you end up at these same parties or functions full of other rich people and people who want to meet rich people and people who want to trade their good looks for your cash. That's who shows up. People bring what they can to the table. These girls don't wanna work — they want to shop all day, maybe go to the gym, take an acting lesson here and there. And I've definitely gotten spoiled — I dated this incredibly hot woman for two years, this stripper. You ever watch Spanish TV? That's what she looked like. You know, in my heart, I know that you don't have to be really beautiful to be sexy, but if you are really beautiful — that's its own kind of power. And power is sexy." Dating a luxury item in the high-end category of the sex industry can also be, well, sexy. His then-girlfriend, who was bisexual, introduced him to some exclusive group-sex clubs, where the ratio of women to men was usually two to one. From all signs, Ken is sounding like someone who might argue that money had dramatically ratcheted up the quality of his sex life. But when the question is put directly to him, there's a pause, then a sigh. "It doesn't seem to be working for me," he says. "I'm telling you, I work all the time, my broker's calling me four times a day. You think about the money all the time. I've become a lot more self-protective and insular. And that's the difference between having sex and being a lover. I recognize this in myself, but I seem powerless to do anything about it." That self-absorption, he admits, translates directly into bedroom behavior. "I'm much less eager to please in bed than I used to be," he says. "But that happens mostly when I feel like they're there for the party or the good time that my money can buy — at times, frankly, it feels a lot more like prostitution than dating. You start to think, this is all coming out of my checkbook anyway, you might as well give me what I want. So what if I fall asleep right afterwards. That's not something I ever would have accepted in myself before. But then you get them defending you to their girlfriends: 'You know, he's just working so hard.'" Hearing the strain of self-loathing in Ken's voice, the deep fatigue, I almost forgive him his callousness. It also occurs to me that I may be projecting the extent of his ennui in an effort to reassure myself. He may confess to dissatisfaction, but he's also not planning on passing any of the good times up. Cameron, the twenty-four-year-old hotshot in Austin, still sounded wide-eyed at his own good fortune when I spoke to him; but I wonder if he is going to sound more like Ken in another fifteen years. For now, Cameron seems unsure of how to judge his new self and surroundings, an ambivalence I heard in his voice when he described the time that he and his manager, "who was, like, married and has kids," flew into New York for his birthday. They went to some strip club, got crazy and dropped a thousand dollars. "Part of it," he says, by way of explanation, "was being in the corporate world, seeing the kinds of things people do that beforehand I would have said were unethical. Now, I didn't see anything wrong with strip clubs. It was part of the corporate culture. When I was going to these clubs, several of my friends would pay the full deal. Take the strippers back with them and have amazing sex — with strippers! The ones I saw, that were absolutely hot, they were, like, two thousand dollars a night." He pauses. "I never did that. I won't deny it, I considered it." He compares the sensation to a fantasy of his. "It's like how I get a massive high on the possibility of, rather than being in my old broken down Nissan, getting a blowjob in a hundred-thousand-dollar automobile. It's just completely different. It's just the concept of being" — he snaps his fingers — "there." In the '80s, my friends and I watched Gordon Gekko in Wall Street and we felt contempt. We laughed at him: he was a cautionary tale, a buffoon. Now, according to the myths of the boom, the rich are — or could be — "us." I have to fight to resist the conclusion that it's no longer enough to be interesting. Sometimes I think it might literally be easier to go out and make that two million than conquer these insecurities. It's not likely to happen anytime soon. But after weeks of conversations with people who were, in one sense or another, "paying for it," I confess that I was curious about the rush of that clean exchange. Unwilling, for obvious reasons, to pay for "it" literally, I settled for paying for a simulacrum. I took myself to a high-end Manhattan strip club. I ordered a gin and tonic. The tables were full of men — at bachelor parties, with clients. The girls — stunning and beautifully distended as any cartoon from an old Bally pinball machine — shimmied before me. I leaned back, half uncomfortable, half bemused, getting into character. In your basic strip club, the sex is pretty sexless. The girls — slick and serpentine — seem more like "girls," a parody of female sex appeal with what appear to be road-side pylons for breasts. But then one swoops down close enough that you can catch a fleeting whiff of perfume from her neck — a brief erotic charge, a hint of the real, the sensual. It's theater, again, but you're right up there on stage with her. She's playing to you, but you're playing to the crowd, your peers. You're spending to be seen spending; you're playing the boy in front of the boys. At these clubs, you have the opportunity — it starts to feel like a gentleman's obligation — to indulge in a lap dance as often as every five minutes. But the first time a dancer I found appealing approached me, I hesitated. I sized up her chocolate-colored hair, her waist the size of a diamond choker, unsure of myself. I flashed back for an instant to the cab stalled in front of my apartment that icy night. Then I reached into my wallet, and pulled out a quarter-inch's worth of twenties, tucking one into the string of her thong, the sole moment of contact the club allows. And I went on to the next. A single lap dance, like first-time sex, feels self-conscious and awkward until you loosen up long enough to learn to go with it. It only feels vaguely right after you've hung in there long enough, peeled off enough of the twenties in your hand, to have crossed a certain point, the point where you finally give yourself over to the the fugue spiral of the casino rush, the druggy sense that money is no longer money, you are no longer you. Your limits are no longer limits, taboos no longer taboos. It's the thrill of unchecked cumulation. The sensation is not exactly sexual, but animalistic, illicit, defiant. It's a high I didn't expect, this momentary loss of self. But for this fleeting moment, I experience that high, and as soon as it's over, I wish I never had. Photographs by Nola Lopez
©2001 Alex Williams and Nerve.com