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The incurable new Bay Area bachelor

Impossibly picky and increasingly desperate, singles from San Francisco to Silicon Valley have a new tool in their search for a solmate: the 21st-century matchmaker. Natasha Sarkisian chronicles a yearlong quest to make one mixed-up man happy in spite of himself.

THIS IS THE STORY OF PETER KUPERMAN, a handsome, slightly crazy, oddly endearing 37-year-old who wants nothing more than to marry a girl who went to Penn. The romantic obsession of his life began in a crowded Chinese restaurant when he was visiting the University of Pennsylvania campus during his senior year of high school. The line of hungry students was long, so Kuperman asked the hostess if he could claim the one empty spot in an eight-person booth filled with seven cute girls. They were members of an all-female a cappella group called the Quaker Notes, and for the next half hour, they bubbled with excitement for music, for their school, even for him. For dessert, they serenaded him with four-part-harmony versions of “A Hazy Shade of Winter” and Cheap Trick’s “The Flame.”

Nearly 20 years later, Kuperman still hears their siren song. After a show that night featuring Penn’s famous all-male drag revue, Mask and Wig, young Peter made two vows. He would catch the troupe’s spring extravaganza every year, no matter what. And one day, he would fall in love with a Penn girl, and she would watch those Mask and Wig shows with him.

As it turned out, Kuperman’s infatuation with Penn was not immediately reciprocated, but he refused to consider another college, and after two rejections, he got in. He majored in computer science and economics, graduating in 1996 and becoming one of those earnest alumni who get all worked up about eccentric causes, like fixing high-rise elevators in the undergrad dorms. After Penn, instead of heading back to his native Toronto, he spent six years in the Bay Area training as a long-distance runner with other Olympic hopefuls on the Nike Farm Team. When that didn’t pan out, he moved to New York, returning to San Francisco in 2006 as the sole manager of his own hedge fund, QED Benchmark. It was such a money machine, Kuperman bragged, “I could travel three weeks a month…and still maintain my income level” ($1 million–plus a year, he said). For fun, he hosted cooking party–salons at his SoMa loft, where local luminaries chopped herbs and talked green technology or stem-cell research. But he was still searching for his Penn girl—and something much more. His perfect partner, he once emailed me, would embody “this whimsical vision of ‘movie love’ where I get so entranced, I would go around the world just to be with her.”

The first time I meet Kuperman, he has just made the 30-minute drive to Palo Alto to consult with his professional matchmaker, Amy Andersen. He is trim, with brown hair flecked with gray, and he has the hypersuccessful Bay Area bachelor look just right: lavender button-down shirt; distressed Diesel jeans; shiny black loafers; intense, unwavering gaze. He seems like the picture of confidence. As he tells me his story, though, his voice quavers and his blue eyes well up with tears. Unsure whether I’m more touched by him or embarrassed for him, I feel my eyes misting over, too. It’s rare that anyone around here ever admits to having a dream, for fear it might not come true; rarer still for a man to pour his heart out about something so goofy and private to a complete stranger—a reporter, no less. It’s clear that, as much as he cherishes his Penn fantasy, it isn’t what he really wants; disappointment seems inevitable, and I’m torn between wanting to hug him and wanting to shake him.

Across the room, Andersen taps away on her laptop, unfazed. She’s worked with hundreds of Bay Area bachelors, each in his way as quirky and mixed-up as Kuperman is, trying to help transform them from dorks or jerks into somebody’s soulmate. It’s a process that gives her unusual insight into the counterproductive longings of the single, spoiled Bay Area male who has become too picky for his own good, yet demonstrates time and time again that he is powerless to change, mostly because he doesn’t think he needs to. Andersen’s job is to help these Lost Boys—Peter Pans, if not Peter Penns—do something they may never have had to do until now, which is open themselves up to compromise, and then to love. The process is painful, sometimes excruciating. No matter how wealthy or self-assured or self-deluded they are, at some point, Andersen says, “most of the guys who come in here cry.”

Blond and svelte in little silk numbers
and Gucci boots, Andersen looks like one of the Real Housewives of Orange County and thinks like a Silicon Valley CEO. She’s never without her BlackBerry and her Louis Vuitton scheduling tome, every page filled from 9 a.m. to midnight with meetings with clients—650 over the past five years. The founder of Linx Dating—as her website describes it, “an exclusive, by-invite-only Bay Area–based dating service created for the ‘marriage-minded’”—is 32, sweet, shrewd, and relentless in her pursuit of her clients’ happiness. Combining the ana­lytics of eHarmony, the social networking of Facebook, and the strange, self-absorbed glamour of The Bachelor, her concept is so tailor-made for the Bay Area and the times that in certain Marina and Peninsula circles, she’s practically a household name.

Andersen’s fee starts at $6,000 for eight carefully matched dates with other great-looking, high-earning Linx members; for $30,000, you get 15 introductions, a nationwide out-of-network search, and a cocktail party straight out of The Millionaire Matchmaker, where a dozen fawning “eligibles” show up to be checked out and vice versa. For those who need it, there’s also date coaching, mock dating, a dermatologist referral, and a fashion and home-decor makeover (in the case of her male clients, Andersen has been known to personally throw out grungy toothbrushes and moldy bath mats). Though she is the matchmaker to the Web 2.0 gene­ration, she advocates a retro version of romance, in which men open doors and women do not talk about their careers.

The familiar stereotype about the Bay Area dating scene is that it’s the women who are dying to get mar­ried. A former member of their ranks, Andersen admires single women here for their intellect and independence but believes they often sabotage their chances by approach­ing a prospective romantic partner the way they would a business partner—reciting their résumés instead of being flirty, asserting their ballbuster side instead of their vulnerability. Andersen counsels her female clients—they make up half her roster, and unlike most matchmakers, she charges them the same as men—to wear pastels rather than black, play down their accomplishments on the first few dates, and admit that horror movies scare them. “It’s kind of pathetic, but it’s true,” says Mary Ann Mullen, Andersen’s sidekick, a sensible, motherly type who’s been married for 18 years and speaks frankly about how men respond to powerful women. “Their pee-pee feels castrated”—here, she lets her pinky droop—“and we want it to feel happy.”

Yet as I hang out in Linx’s knickknack-filled offices—conveniently located between those requisites of modern-day marriage, engagement-ring central (Diamonds of Palo Alto) and a couples therapist—I’m surprised to discover how many Bay Area men are desperate, too. Mar­ina guys in Tom Ford sunglasses who’ve spent a decade or more jumping from windsurfing to heli-skiing to kiteboarding, and to younger and younger girls, suddenly start feeling creepy and pathetic. The wealthy tech­nology wizards look up from their turretlike workstations and realize that their world is devoid of, and even unwelcoming toward, women and that their social and emotional development ended with their first programming job. Online dating doesn’t work for this high–net worth crowd. “To avoid gold diggers, people downplay themselves in their profiles,” Andersen says. “The end result, when you’re finally face-to-face with someone you met online, is that you’re a liar.” Meanwhile, the social media they rely on to stay connected—texting, instant messaging, tweeting—reduces actual human contact and further stunts their ability to interact with the opposite sex. That’s where Linx comes in. “It’s what we say over and over—dating is a skill,” Andersen tells me. “We’re like grad school for finding your future husband or wife.”

Andersen dreamed up Linx at the height of the Internet boom, after many a night spent downing beers at Nola, in Palo Alto, with her then boyfriend and his single pals as they bemoaned the dearth of available women in Silicon Valley. She knew where the girls were: “They were all up in San Francisco in the Junior League, desiring the same thing I wanted: marriage!” When she and that boyfriend (aka that “noncommittal, cheating boy trapped in a 35-year-old’s body”) broke up, she fled back to the city. One failed long-term relationship later, Andersen was in no hurry to couple up again. “At one point, I had, like, five amazing guys courting me with massive bouquets, gifts, and trips, walking across fire for me, and I thought, ‘This is pretty cool.’”

It was also great research. A born entrepreneur—as a kid in Mill Valley, Andersen cut flowers from neighbors’ yards, wrapped them in tissue and ribbon, then resold them to the people she had stolen them from—she fleshed out her dating concept while working in private client services at Merrill Lynch. (Even for someone with so much natural chutzpah, cold-calling rich people—up to 225 a day—provided “an incredible skill set,” she says.) Andersen quit that job to launch Linx in 2003, operating out of a Starbucks on Russian Hill and meeting with as many as seven “high-caliber” clients—attorneys, doctors, venture capitalists—a day for free. She earned her first paying client, a VP of marketing for a web company, in February 2004: eight setups for $1,200. “When people stopped blinking at $2,600, I went to $3,000, $3,200. Then I realized this demographic was not concerned about price at all.” Indeed, matchmaking turns out to be recession-proof. Last fall, even as the economy was crashing, one of Andersen’s clients upped his “marriage bonus”—many of her contracts include a fee for matches that make it to the altar—from $25,000 to $100,000 because he couldn’t face the thought of turning 40 alone.

Before a friend referred him to Andersen a year ago, Kuperman had already sought professional help in finding his Penn mate. He’d had plenty of girlfriends, but his enthusiasm (or theirs) usually waned after a few weeks. Online dating was no help: “It’s like walking through an airport or a mall and talking to strangers,” he says. So, in 2004, he consulted semifamous New York matchmaker Samantha Daniels (the 2003–2004 NBC series Miss Match, starring Alicia Silverstone, was inspired by her career), a gorgeous Penn grad with a great network of alums to draw from.

In his Linx application, Kuperman admits to having blown the first match Daniels arranged, with a Penn grad who was getting her MBA from Columbia. The second introduction, to S., went much better, but within six months, they were kaput, too. One of his biggest gripes: S. was not sufficiently enthusiastic about his favorite movie, Love Actually. (“She said at the end, ‘Cute movie,’ implying, ‘That’s now over; let’s move on,’ and not, ‘Wasn’t that story about the 10-year-old kid so unbelievably romantic?’”)

Much of what I know about Kuperman comes from his 14-page application, which he shares freely with me a few days after we meet. I have to admire his guts for letting me see it; god forbid anyone should ever see my wish list for a husband. One section asks clients to check as many adjectives as apply to them from a list of 78 possibilities, including “Darwinian,” “loquacious,” “narcissistic,” “life-of-the-party,” “autophobic,” and “wise.” Andersen wants to know: What is the worst decision you’ve made at your current job? How is your relationship with your family? Do you hold any patents? Besides helping her understand her clients, the answers weed out the losers, like the 42-year-old Google exec who’s still living with his mother. She’s equally on guard against commitment-phobes—guys who pull the breakup card just when you’re starting to look at rings—and people who are just looking to hook up. Half of her applicants don’t make the cut.

For his part, Kuperman shares the average guy’s interest in sexy underwear and Rachel McAdams, though not in Jennifer Garner or Scarlett Johansson. He answers yes to children, no to a nanny, picks private over public schools, and reports an IQ of 162. His favorite food is “freshly picked sweet corn on the cob bought at a roadside stall...on the way to cottage country,” and his favorite pastime is swing dancing: “I can see us dancing every day for the next 100 years.”

The most surprising question for me is “Describe your ideal wedding.” I’d assumed this is something only women fantasize about, but Andersen insists, “Men usually have it completely mapped out.” Kuperman proves her point: “Formal black-tie ceremony, nonreligious setting (e.g., estate, vineyard, etc.), bach­elor/ette party, but not too wild (i.e., no overt sexual contact with me or her, but strippers are okay), we share the responsibility of planning, I pick the band.” The first dance will be “a showpiece of excellent dancing ability...the language of the conversation that happens when two great dancers get together and let their bodies speak to the musicality of the song.” As the music fades, the crowd will leap to a standing ovation. “That’s really important, too. :-)”

Reading the application makes me squirm, as if I were sneaking a look at someone’s diary or eavesdropping on a session with his shrink. I always suspected Bay Area single guys were impossible to please; now I have proof. Kuperman’s fantasies, like those of so many men I’ve met here, are right out of a silly romantic comedy. He comes across as lovable in some ways, immature and irritating in others. I can feel his genuine longing for a deep connection, but I also see the internal hurdles he erects—so many that I wonder whether he really does want to fall in love and settle down.

The best evidence of his ambivalence is a remarkable document he appends to the standard Lynx application: eight single-spaced pages of “musts, shoulds and what do I have to be,” along with a two-page discussion of his two most significant recent relationships. The musts include “all-natural body parts,” “love celebrating New Year’s Eve,” and “be okay with a shower with two heads on opposite walls.” On a sweeter note, he expects his dream girl to be “really close with at least one family member” (his own relationship with his two sisters is “one of my biggest areas of happiness,” he writes) and “be someone who constantly says ‘I believe in you’ to their children.” But she also has to “allow me to indulge in a luxury sports car and be willing to fill the car with premium gasoline to extend the life of the car and increase resale value.” Maybe he’s joking, but I don’t think so.

Kuperman’s words make me wonder
about Andersen’s pro­cess. Is it really prudent to encourage people—especially Bay Area singles who are used to having their own way in almost every aspect of their oh-so-perfect lives—to spend so much time and energy focusing on what they want in a mate, as if they were configuring a new computer or ordering coffee at Peet’s? Doesn’t this just close off their options and fuel their self-defeating fantasy that a relationship is all about them?

But after reading hundreds of these applications—brain dumps, really—Andersen has learned what to take seriously and what to ignore. She sees Kuperman’s blatherings as therapeutic, rather than alarming; the whole point is for him to get stuff off his chest so that she can help him examine every tiny piece of his fantasy, recognize what he really wants, and come to terms with how to achieve it. Andersen spends her days listening to male and female clients check off their lists of “musts” and “shoulds”: no shorter than 6 feet, no smaller than a C cup, no professors or accountants, no kids, no salary under $500K a year. By comparison, Kuperman’s Penn dream strikes her as substantive, even old-fashioned. People used to grow up in small villages and marry their neighbors; the truth is, you might have more luck finding your soulmate in a pond of 50 than in an ocean of a million web profiles. The Penn requirement, Andersen optimistically concludes, “will be a fantastic catalyst and accelerator for a happy relationship.”

Andersen has facilitated dozens of such relationships over the years, including four marriages and at least 30 long-term couples. She suspects her success rate is actually higher: Once they’ve met someone they really like, “clients often go radio silent,” she says. (She found out about one recent engagement by stalking the lovebirds on Facebook.) But helping clients find lasting love often means Andersen must be brutally pragmatic—and force them out of their comfort zone. “So many frustrated people say they want to meet ‘the one,’ but they don’t change their patterns,” she says. “They stay in the Marina. They keep trying the same places—Encore, Symphonix, the Matrix—where, no surprise, they run into the same people. You have to do something drastic.”

Andersen speaks from personal experience. Not long after she started Linx, she found herself in her own rut, dating up a storm (including at least one prospective client), but no closer to marriage and kids. On an impulse, she decided to move back to “target-rich” Palo Alto and take a six-week dating hiatus. She got a nutritionist and a stylist, did an ashram diet and cleanse, “and then I was in the right place.” In the end, she needed her own match­maker, a friend who introduced her to Alex Gould, a Stanford economist and media consultant. Ten months later, he stunned her by proposing in front of 125 of her clients at a Link & Drink networking party at the Four Seasons Palo Alto. “I woke up at 5 the next morning and looked at the ring and thought, ‘Ohmigod, I’m engaged!’” (The enormous sapphire gets so many yearning looks from clients that Andersen and Gould, who sometimes helps with the business, ought to consider writing it off.)

Still, after months of watching Andersen in action, it’s hard for me not to conclude that her female clients are expected to make the most drastic changes. (Is there anything more depressing than telling an attractive, accomplished woman to pretend to be less than she is so men won’t feel threatened?) For her male clients, Andersen advises basic good manners: Pay for dinner, never text or email to arrange logistics, spend time listening to your date instead of just talking about yourself, give every setup at least a second chance. Anxious or nerdy types can have a dating coach attend events with them incognito and give them real-time feedback and support. Ander­sen also works on the Too Much, Too Soon syndrome—“prob­ably the most common thing we see,” Mullen says—and the closely related male tendency to go on and on and on about themselves, their jobs, their hobbies, their exes. The solution is a strategy known as KISS: Keep It Simple and Succinct. Andersen coaches her clients to think of first-date conversation as a tennis ball they want to keep lobbing back and forth. “We help them narrow it down to 15 sound bites. Then we have them visualize a tape recorder: Press play. And now press stop.” They also work on what Andersen calls “strategic positioning”: “I hate my job and am on the verge of chucking it—along with my six-figure income” becomes “I enjoy tech but have thought of trying something new.”

Andersen decides that Too Much, Too Soon is also Kuperman’s biggest problem; he’s “the kind of guy who writes a girl a 14-page letter after one date,” she tells me. For his part, Kuperman seems to trust her judgment completely: “When I met Amy, I had an extremely strong guy reaction that said ‘WOW! I just met an incredibly important person in my life,’” he recently wrote. Over the weeks, they work mainly on taking things slower—“not jumping in because he feels a lust or attraction,” Andersen says. He appreciates all the rules she sets. By “laying down the protocols,” he says, Andersen eliminates much of the second-guessing that can make going on a date—especially with a stranger—so nerve-wracking. When both parties feel comfortable, it’s much easier to connect.

But when I meet Kuperman, two months into his Linx experience, he still hasn’t connected with anyone. Andersen has scoured Northern California for Penn grads and sent him on several dates, but no one has set him on fire. After every fix-up, he sits down with Andersen and Mullen to rehash the encounter and plot their next steps. They’ve just about exhausted the eligible pool of Penn women in the Bay Area, and Kuperman knows it. “It’s like a Venn diagram,” he finally tells them. “There are smart girls and hot girls, but not a lot of intersection.”

In the past year or so, Andersen and Mullen have added another tool to their arsenal: the VIP mixer, where one or two clients (usually male) are surrounded by a dozen or more “eligibles” recruited from Facebook and other sources. The idea strikes me as both demeaning and a significant departure from the original Linx concept of carefully matching couples and striving to make their interactions as stress-free as possible. But many of their clients love feeling like the stars of their own reality show—plus, even if no individual candidate bowls them over, the whole experience does. Kuperman, who’s considering moving back to New York—with the exception of Philly, the Penn grad capital of the world—likes the idea of holding his party there. So does Andersen, who’s dying to introduce Linx to the East Coast. Even if Kuper­man doesn’t meet “the one,” she figures the event might help him overcome his Too Much, Too Soon issue; with so many candidates to choose from, it should be impossible for him to get overly attached to any of them.

The next few weeks are a blur as the two Linx women make the arrangements, aided by Gould (Penn class of ’93). They set the date (mid- to late October), book the celebrity-magnet Carlyle hotel, and cold-email more than 350 New York–based Penn graduates, 200 of whom reply. Phone interviews narrow down the final list to 19 sensational candidates, including an advertising executive and a pediatrician. For the first two days, Kuperman will have a series of one-on-one meetings with 12 women, followed by dinner dates with each day’s “winner.” Day three will consist of the final one-on-ones, then a cocktail party with a new bevy of candidates. By my conservative estimate, Kuperman’s tab for the whole trip will approach $40,000.

Arrangements are in the final stages when the global economy implodes. Then Kuperman, who went to Can­ada to visit one of his sisters over Labor Day, has a problem with his work visa that delays his reentry to the U.S. by several weeks. The day before the Linx entourage is supposed to check in to the Carlyle, he finally talks the U.S. State Department into giving him a seven-day tourist visa.

When Andersen arrives in New York, Kuperman has another surprise: His mother is in town, visiting his other sister in Brooklyn, and the two women want to meet his matchmaker. Over breakfast the next morning, Mrs. Kuperman pooh-poohs her son’s outfit, which Andersen picked: Nordstrom shirt, blazer, and pastel pocket-square combo. He changes as soon as he returns to the hotel. Otherwise, his mood is upbeat—almost strangely so. This is the week of October 20, and the stock market is having a psychotic breakdown, swinging up and down by hundreds of points every day. But Kuperman the hedge-fund manager seems largely oblivious.

Meanwhile, Andersen and Mullen set up a makeshift office at a table in the hotel’s gallery tearoom. A butler stops by regularly to replenish the tiered silver trays with little sandwiches, tartlets, and scones with clotted cream and jam. The first day’s prospects chat with Andersen and Mullen for 45 minutes or so before being ushered around the corner for a coffee, lunch, or afternoon champagne date with Kuperman. “Peter is more Gap than Ralph Lauren, more hybrid car than Ferrari, more Nestlé cocoa than Scharffen Berger,” Andersen explains, nailing her client’s brand. She tells candidates about her own romantic success, how she met Gould, and how her father proposed to her mother seven days after they met.

A sophisticated 26-year-old brunette named E. emerges as Kuperman’s favorite of the day. Her parents met at Penn, and her family includes 33 alums. Andersen arranges a candlelit dinner for the couple, complete with calligraphy place cards, Veuve Cliquot, lobster bisque, rack of lamb, and chocolate soufflé (ordering dessert is another of her first-date rules), and when she and Mullen return three hours later to spy on them, they’re still at the table, flirting. “I had chills riding the elevator back up!” says Mullen. “I was like, ‘Babies are being made right now!’” (For the record, she uses the phrase “I have chills” at least three times a day.)

Day two’s winner is M., a high-ranking ad exec in an elegant shift dress and three strands of giant pearls. Andersen has a waiter interrupt M.’s one-on-one with Kuperman because his next date has been waiting for half an hour. As Kuperman walks up the steps, he turns around and tells the duo, “She gets my pretty-underwear thing! She wears pretty underwear!” Andersen, half exasperated, half excited, gasps, “Peter!” as he runs off with his next date.

By day three, Kuperman is worn out, and his seams are starting to show. He snaps at Andersen and seems overwhelmed by the number of, as he calls them, “connections” he’s making. (So much for hoping the weekend blowout will cure him of his tendency to plunge into things too quickly—it seems to be having the opposite effect.) The second of his back-to-back meetings in the afternoon goes so well—or he’s feeling so rebellious—that he and his date sneak out of the hotel. Andersen receives a text from the woman saying Kuperman will be back 15 minutes before the bachelorette event, but as the guests arrive, he’s a no-show. The next day, we find out what happened: He and his date walked through Central Park to Balducci’s to buy vodka, chocolate, and popcorn, then headed back to her apartment on the Upper West Side.

Though clearly irked by Kuperman’s rudeness, Andersen is composed, smiling and making sure the champagne glasses stay full. Once again, I’m blown away by the quality of the women she’s managed to assemble, though one overeager candidate has donned a Penn skirt with icons of the Liberty Bell and the Philadelphia Inquirer. The chef has prepared some of Kuperman’s recipes, including chocolate-vanilla pots de crème served in espresso cups. Peach roses and hydrangeas overflow from vases. Several of the women remark offhandedly, “This is so much like the TV show.” When Kuperman saunters in, 45 minutes late, he acts as if he’s right on time. He regales his guests with a story of bringing a girl back to his Penn dorm room, innocently changing into corduroy PJs, and telling her he was going to bed without her.

M.—the only one of the previous day’s dates to be invited—marvels, “This is every man’s dream!” She makes a clear attempt to distinguish herself from the other women by standing apart and talking with the pianist or Gould. It takes a while before Kuperman finally greets her, but less than five minutes later, they retreat to his bedroom, posing seductively for a magazine photographer, his hands all over her legs. After the impromptu photo session wraps, Kuperman, Andersen, Mullen, and Gould break into golly-gee renditions of “New York, New York” and “Night and Day.” Eventually, Gould forces everyone out, leaving Kuperman and M. alone in the suite.

Kuperman, Andersen, and Mullen meet over coffee and crois­sants the next morning to decide what to do with their girl glut. Every candidate but one has already emailed or texted to say she hopes Kuperman will be interested in seeing her again. I’m shocked; assuming they aren't all gold diggers, maybe the idea of vying for one man has brought out their competitive streaks. In the suite, dozens of votives from the night before flicker eerily. Mullen is in her sweats, sans makeup, but Andersen’s hair is still in the French twist she wore to the party.

Andersen pushes Kuperman to share his thoughts. “Could you close your eyes and see your wedding with one of them?” she asks. “I don’t close my eyes and see weddings after one or two days,” Kuperman replies. “That’s your job. My job is courting someone and just having fun. But if I ask M. on this trip to London, and we end up going to New York together, and we
end up doing a couple other trips, then it’s a different story.”

“Oh!” Andersen exclaims. “So you’re talking about a London trip with her? That’s great! You drop these things like hydrogen bombs.”

Kuperman decides to put all the women other than M. “aside,” but he tells Andersen and Mullen to messenger each one a single flower unique to her personality. “This isn’t just some random coffee at Starbucks with some random person from Match.com,” he says. “We’re going to take care of them.” With that proclamation, he dashes out the door to catch a train to his beloved Philly, to meet yet another Linx setup, a med student who wasn’t able to attend the New York soirée—leaving what must have been a $20,000 hotel bill behind him. And after 100 hours of not setting foot outside the confines of the Carlyle, Andersen packs her bags.

A week later, in Andersen’s office, Mullen prods Kuperman to explain why he’s picked M. “She’s hot, and she has nice energy,” he responds. Mullen then asks Kuperman what M. likes about him. “I have a great sense of style and fashion,” he replies. It’s unclear whether he’s serious. “Thanks to us,” Andersen interjects, and everyone laughs. He meekly concurs: “I’d be showing up in flip-flops at the Carlyle without you.”

Kuperman then voices concern about having to do all the work in the relationship—the flying back and forth to New York, the dinner buying, and so on. He feels like M. isn’t putting in enough effort. “We all know how valuable you are,” Andersen retorts. “But we also know that she represents the gold standard. Sometimes you have to put yourself out there, even if you get shot down.” Gould encourages him to “embrace the uncertainty,” and Mullen suggests he write in a journal whenever he feels hesitant about taking the next step.

Gould adds that Kuperman needs to get to know M., which has been the problem all along—he leaps in and out of relationships, never hanging around long enough to become truly intimate with a woman. When I hear Gould’s words, I’m tempted to shout, “Thank you!” Finally, someone is standing up for the women—and it’s not Kuperman’s female matchmakers, it’s a guy who isn’t getting paid to hold Kuperman’s hand and indulge his unattainable quest for female perfection. Like so many Bay Area single men, Kuperman has always fantasized about a relationship on his terms. But M. is “a woman who can pretty much do and have most things,” Gould points out. “I would argue that the reason she doesn’t have a huge ring on her finger is that she hasn’t found a guy who can unlock her. If you can intuit her, that will send you miles.”

It’s great advice, but Kuperman doesn’t seem to hear it, and Mullen is beyond frustrated. “Um, is there some com­moditization of the girls going on?” she finally asks. “No,” Kuperman insists. “Good, good,” Mullen jabs back. “Love to be wrong.”

But as we get up to leave, Kuperman says, “We can do this again in Chicago in February, right?”

It’s nine months later, and Andersen’s business is booming. Economic instability has made the Bay Area’s lovelorn more eager than ever to find solace in a committed relationship; singles in Seattle and Los Angeles have also been seeking her out. I wonder how many of them are truly willing to do what it takes to meet their match, and how many will continue to
insist on having it all—even if it means ending up with no one.

Meanwhile—surprise, surprise—Kuperman has yet to find his perfect Penn girl. After a few rendezvous in New York, including one spontaneous “booked on Friday, see you on Saturday” trip, Kuperman and M. decided there was no spark. But the quick demise of that relationship is the least of his problems. This past March, the U.S. immigration authorities concluded that Kuperman had overstayed his tourist visa by more than three months, and banned him from the country. Andersen has continued to set him up with Penn grads, including an “amazing” woman who met him for a fling in Venice, but this can’t go on forever.

In June, I email to find out how he’s doing. His response is rambling and reflective, even sad. Thinking back to New York, he says, “The real story is that I was completely discombobulated.... I had immigration stress, not-being-at-home stress, and a situation where I was not at all centered and balanced.... I just wanted to get home to San Francisco.” The trip was “fantastic and so much fun,” but, because of his state of mind, ultimately fruitless: “No girls really stood a chance.... And that is a major shame, because I met some incredibly high-quality, amazing, sexy, intelligent, and grounded women.”

What has he learned from working with Andersen? His answer is unexpected. “It seems that I am a very confused, dysfunctional, and indecisive man. I want this WOW! exper­ience…. I am not going to go forward with a long-term committed relationship until I find myself madly in love.” He con­­fesses, “I’ve presented myself to Amy as this person who is totally ready to get married, and intellectually, that is true; but practically, that switch is definitely not turned on.”

He mentions a woman he’d been seeing for a few weeks right before he sought out Linx. She wasn’t a WOW! either, but her kindness to him during his Canadian exile has made him think. “What if I should just grow up, pick someone, and doggedly and determinedly stick with that choice because she is good for me?” On the other hand, he adds, “What if I spend my entire life constantly doubting and tweaking and tinkering and thinking and am never able to just go for it and take a leap of faith?
“Biggie enough answer for you? :-)”

Natasha's Sarkisian's last major piece for San Francisco was "The Admissions Whisperer," in May 2008.