FORTUNE — Amy Andersen was on a date. It was one of several with a venture capitalist that a friend had set her up with. On paper, he seemed ideal: mid-30s, funny, good-looking, athletic. But as they saddled up at Harry’s Bar, a cherrywood-lined sports haunt in San Francisco’s Pacific Heights, the evening took a wrong turn. “He was looking around the room and surveying,” she explains. When Andersen, a striking blonde, asked him what he was doing, he smiled and confessed he was scouting for the “BBD:” the bigger, better deal, or in this case, woman. “I was horrified.”
Such horror stories may be commonplace, but in Andersen’s case, something positive came out of it. The 36-year-old entrepreneur founded Linx Dating, a Menlo Park-based matchmaking service. And in the decade since, she’s fashioned a reputation among tech executives, entrepreneurs, investors, and publicists as a modern-day Silicon Valley yenta. Her 750 “active” clients — individuals who have signed up just within the last two years — include employees of companies such as Apple (AAPL), Facebook (FB), Google (GOOG), Amazon (AMZN), Oracle (ORCL), Salesforce (CRM) and run from early twenty-something entrepreneurs to retired tech execs and investors in their sixties. Those clients may be potentially paired up with the 250-plus clients who aren’t actively seeking a date at the moment or the 19,000 additional people in Andersen’s database, a mix of referrals and people who signed up for the company’s newsletter or mixers. Of her active clients, at least 90 are in exclusive relationships, and 38 are now married. (None have divorced.)
Her services aren’t for the cash-strapped. A basic plan may cost $2,500, while a customized V.I.P. service starts at $50,000. The former nets an unspecified number of introductions over the next two years. The latter adds a slew of extras, including wardrobe shopping and long lessons in proper social etiquette. “They have the resources — they have everything lined up in their life, academically and professionally speaking — but not the social resources, or in some cases, the social graces to meet the right one,” says Andersen.
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In the case of one V.I.P., a divorced twenty-something coder at a gaming company with extreme social anxiety, Andersen spent 16 hours coaching him. They tossed his ratty jeans and smelly sneakers and bought new outfits. She walked him through a mock-date scenario, prepped him with talking points, taught him how to maintain eye contact, even how to properly hug vs. a stiff slap on the back. And because he rides a bike to work, she arranged for a car service to pick up his date.
In many ways, Linx is the antithesis of online dating services like Match.com and OkCupid, a $1.2 billion industry that has transformed the way people court. While online is now the second-most popular way couples meet, Andersen argues that in many situations, a matching algorithm, like the one OkCupid employs, doesn’t cut it. Online may help some, but deter others, fostering a pick-and-choose shopping philosophy that someone better is a click away or just around the corner.
It’s this so-called BBD mentality that Andersen dislikes. “When I sometimes work with clients, I have to retrain them,” she explains. “I have to tell them to slow down their thinking, especially when they’ve become very used to that high-volume, grass-is-always-greener sort of mentality where it’s quantity over quality.” Explaining that difference, how the advantages of her services trump online, can be challenging. But Andersen finds many of the clients who come to her have either become disillusioned by their online misadventures or, in the case of many tech types who work long hours, seek a more hands-on approach.
“The role Amy provides is that intuition, that sixth sense that goes along with evaluating people’s personalities and desires,” explains a 60-year-old ex-tech exec and serial entrepreneur, who had skimmed Match.com but sought a service with more filtering. To wit, Andersen follows a procedure more stringent than the college application process, with a series of pre-screening questions via e-mail, a one-hour meet-and-greet (so she can get a feel for a client’s personality), and a 12-page application with questions like, “If we were to ask the ‘ex’ to describe you, what honestly do you think he/she would tell us about you?”
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Indeed, Andersen mandates hard copy photos of exes, along with photos of non-celebrity individuals the client finds attractive. Another separate interview dives into the metrics of what the client is seeking from his or her match, factoring in looks, education, occupation, political views and the like. It’s so strict in fact, Andersen says she turns away four out of every 10 people who approach her.
It’s paid off for some. In the case of the ex-tech exec, he met his wife after two years as a V.I.P. client and four dates — and short-lived relationships — arranged by Andersen. In early 2011, she arranged for him to meet a match on their first date at Jardiniere, a French restaurant in San Francisco. “Amy said to me, ‘I think this could be the one,’ and I was like, ‘Yeah yeah, sure,'” he remembers with a chuckle. But things worked out: “I was like, wow, now we’re talking.” Four and a half months later, Andersen helped him plan out the proposal by renting out an oceanside suite at the Ritz-Carlton in Half Moon Bay embellished with candles, rose petals, floral bouquets, and Mariah Carey playing in the background. The two married last fall.
Another client, a busy thirty-something startup co-founder living in San Francisco, sought out Andersen after trying Match.com and meeting a few duds for dates. “I was getting 400, 500 responses a day, and it’s kind of like, if it was possible, I wanted to hire someone to go through them for me!” she half-jokes. After signing up with Andersen last November, she was matched with four different men. When one she liked, another startup founder, remained noncommittal, Andersen stepped in and advised the client to make herself unavailable. The “hard-to-get” tactic worked, and the two became exclusive last February.
Each client that pairs off becomes another validation of Andersen’s anti-BBD philosophy. Says Andersen: “To those people who say, ‘Well, I want more. Can’t I have multiple people at once?’ I tell them, one at a time. One at a time.”
