$150k to find love? Inside the high-stakes Silicon Valley matchmaking scene

Over the last 22 years, Amy Andersen of Linx Dating has earned the monikers the “Cupid of Silicon Valley” and the “Matchmaker for Millionaires” thanks to her ability to pair up elite Bay Area singles.

“My typical VIP client has been extraordinarily successful in their career and achieved goals above and beyond their wildest dreams,” she said. “Their time and privacy are very important to them, so dating apps or websites are not going to work.”

Andersen’s services don’t come cheap; rates start at $150,000 and quickly go up from there. And she earns it, catering to a clientele whose extreme wealth, exacting standards, and occasional eccentricities can make finding the perfect companion a challenge.

Andersen and four other matchmakers consulted by The Standard say sparking love in San Francisco and Silicon Valley comes with a unique set of complexities. Paying clients tend to be busy, high-powered, and work-obsessed, with a prominent nerdy streak (because, yes, they’re mostly in tech).

Helping them find love involves navigating awkward wealth dynamics, shooting down unrealistic expectations, and unflinchingly taking on topics like orgies, autism, and whether Burning Man attendance is appealing or appalling in a potential beau. 

“There’s an inclination to look at people like resumes,” said Simone Grossman, a matchmaker from Three Day Rule who focuses on the Bay Area. That can mean that matchmakers must dissuade clients from creating elaborate spreadsheets to quantify or rank dates, or have difficult conversations about how finding companionship might feel harder than their recent billion-dollar exit.

Matchmaking in this market can also mean managing big egos and people unaccustomed to hearing “no.” Or those who expect miracles.

“If someone wants me to be a magician, I don’t take on those searches,” said Shannon Lundgren, founder of matchmaking firm Shannon’s Circle. “Sometimes who they’re looking for is a unicorn — or someone that’s not looking for them.”

Andersen has encountered a similar dynamic: “I turn about 98% of business away,” she said, adding that she often refers folks who aren’t the right fit to other local matchmakers. (All in, she prefers to have 10 or fewer paying customers at a time.)

Getting the ball rolling is not unlike starting a new executive role. Once a client gets onboarded — a multi-hour process probing someone’s deepest hopes and desires — their matchmaker becomes a mix of advocate, coach, confidante, and therapist. And it can require dropping everything to offer advice or a listening ear when needed. Andersen recently ran into one VIP client at Equinox, for example, and her workout plans turned into an hourlong session chatting on side-by-side treadmills. 

Customers can also take advantage of services like wardrobe consultations or home-vetting visits, where their digs are inspected ahead of any overnight dates. A matchmaker may have to gently explain to a widow why having dozens of pictures of their deceased spouse could dampen the mood, even if they’re cooking up a dinner of aphrodisiacs. Or tell someone with a lot of clutter that their stacks of paper, miscellaneous (read: poorly curated) art, or random stacks of books are giving “hoarder” instead of “eligible bachelor.” 

In addition to their paying clients, matchmakers keep extensive databases that contain prospects, or non-paying members that could pair well with their clients. And intake conversations for those potential suitors also require some questions that feel particularly Bay Area. 

For example, a certain annual desert bacchanalia can be a point of contention. 

Some clients “are staunchly anti-Burning Man: That’s a deal-breaker for them,” Grossman said. “But I also have a lot of clients who are regular Burners and couldn’t see themselves with someone who is against it, that they would perceive as closed off or square.” 

Psychedelics and other mind alterants are also divisive. Lundgren recently realized she had to expand her drug-related questions for prospects because of how differently certain sects of the Bay Area perceive microdosing mushrooms or ketamine.

One client recently told her that he’d been on a date where the woman he matched with said that her goal for the year was to do more drugs. He was horrified. “That can be a real value difference between two people,” she said. 

Orgies — or at least discussing them on the first date — can be a deal-breaker too. One 30-something man who works in tech and went on several dates through a matchmaker as a free client said shortly into a first date over lunch in the Marina, his match, a paid matchmaking client, brought up her proclivity for group sex and bluntly asked about his own preferences. 

From the out-of-nowhere directness of the question, he suspected his date was on the autism spectrum. This, too, comes up at times in the Bay Area matchmaking world, where a client may need to be coached in conversational do’s and don’ts that might not be intuitive for them. (Post-date, both parties debrief with the matchmaker, so the client may receive direct feedback on any negative trends in how they presented.)

Politics has been another touchy subject as of late, matchmakers say. Once deep blue and largely atheist, the Bay Area has experienced a shift toward both God and conservative politics. Matchmakers find themselves needing to explicitly ask prospects whether they voted for Trump — since their answer is likely to be either a bright green or bright red flag.

“Given the world we’re in right now, I have to put politics more to the front of the bus than ever before,” Lundgren said. 

Matchmakers can also screen for financial parity, since clients paying multiple hundreds of thousands of dollars for their services often like to date someone in a similar income bracket. For those more open to different echelons of wealth, the goal is warding off gold diggers. 

Andersen said that one mid-20s applicant to her database recently said in a screening that she was looking for a partner with a “minimum $30 million net worth.” Given the disparity with the applicant’s own holdings, she did not make the cut. 

For the orgy-shy techie who went on several matchmaker dates, the wealth of his pairings could be staggering. He recalled one evening where he picked his prospective partner up at a compound with armed security guards and quickly realized the gap between them was too wide. “This was just not going to work,” he said. “We just lived in different worlds.” 

He still picked up the check for their luxe dinner. 

Matchmakers also sometimes have to nudge clients away from hyperspecific requirements for attraction. Or being impractical if they’re a six who is adamant about only being paired up with 10s. 

“If there’s a disconnect between what they’re looking for and what we all know to be reality, it’s a problem,” said Jennifer Wills from Kelleher International. “It could be somebody saying, ‘They have to have these 72 qualities.’ Well, that combination might be almost impossible to find.”

Though, for the right client and the right price, the matchmakers will certainly try. As Grossman put it: “No stone unturned and any avenue possible.”

Andersen has personally scouted prospects at the J.P. Morgan Health Care conference or law firm cocktail parties. Other tactics a matchmaker might employ? Messaging hot people on Instagram or using LinkedIn’s advanced filters to find the winning combination of college education, executive title, and location. 

“For clients, it’s a massive investment timewise, emotionally, and financially, so there’s a lot of pressure. I have to be able to really deliver,” Andersen said. “But the secret sauce of matchmaking is that it’s often the candidates that are a slight deviation outside of someone’s original thinking that are the winners.” 

Because the Silicon Valley tech elite are often well-known in certain circles, they may require their matchmakers to have discretion in revealing their names to potential dates. Security-focused platforms like Proton Mail and Signal are often the norm for communication.

One particularly well-known client had Andersen schedule phone calls versus in-person meetings with new suitors, since he was nervous to be seen in public on anything that could be perceived as a date by those who could recognize him.

Generally, dinner and drinks reign supreme for early outings (though Andersen had one client whisk their beau on a private jet to Paris, where they embarked on a private dinner cruise on the Seine). But matchmakers also sometimes see customers take a distinctly Bay Area approach, like cold plunging, trail running, or a hike through the Marin Headlands. 

Wes Myers, co-founder at AI-assisted matchmaking company Keeper, had one Bay Area couple whose first date ended up being 12 days long: They started with a park walk and then decided to directly launch into a camping trip. 

His company’s premise is based on the idea that giving people extensive questionnaires about their preferences, personality, goals, attractions, IQ, and, yes, where they land on the autism spectrum, and then letting an algorithm surface their ideal partner will ultimately be a better solution than old-school human matchmaking. 

“Once you have enough people and you’re able to weigh all these elements correctly, you can pair people pretty efficiently and fairly reliably predict if they’re going to be happy and want to spend their lives together,” he said. 

An ambitious goal, to be sure, and right now Keeper still taps humans to sort between the several dozen matches a single may receive. 

The human matchmakers, for their part, by and large argue that there’s no way that AI will ever be the best fit for a certain kind of client. For the same reason these people tend to shirk dating apps — too time-consuming or public, limited in their candidate pool, or flawed in their matching algorithms — they will always prefer working with a real live matchmaker. 

“Many of my clients have built these AI technologies or different dating apps, and yet they’re choosing me,” Andersen said. “They might embrace technology and be responsible for it, but when it comes to matters of the heart, they’re choosing an actual human being to do the job.”