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It’s late morning, and Peter Rudolph, the executive chef of Madera in the five-star Rosewood Sand Hill hotel in Silicon Valley, is commuting from San Francisco to Menlo Park. The hotel opened four years ago on Sand Hill Road—a veritable venture-capital office park—near Woodside, home to many tech billionaires. Surrounded by three of the wealthiest Zip Codes in the country, its high-design interiors and higher-powered happy hours have given a county known for coding a new sense of cool.

Halfway to the hotel, Rudolph pulls into Starbucks for his morning coffee. At the counter as he orders a tall Americano, Rudolph is surprised to see the word “Rosewood” scrawled in pen on the barista’s hand. Granted, he has just won a Wine Spectator Award of Excellence, but he is still curious as to why a Starbucks server half an hour away has tattooed himself with the hotel’s name. He has to ask.

“Excuse me, why do you have ‘Rosewood’ written on your hand?” Rudolph inquires.

“Because, dude,” the barista replies, “my friend told me if I go there on Thursday night I’m guaranteed to get lucky!”

Rudolph is dumbfounded—yet aware of what the guy is talking about. He had begun to see a pattern developing. Along with the usual lines of luxury cars came a crop of town cars and taxis dropping off ladies of a certain age—Thursday night at the Rosewood is what’s known locally as “Cougar Night.”

The hotel doesn’t exactly list it on its official calendar, of course. “There’s no question that we have become one of the regional hot spots for that scene on Thursday nights,” says Rosewood Sand Hill managing director Michael Casey. “But to call it Cougar Night to me is far too limiting for what really is the Beautiful People of Silicon Valley taking part in the social scene with the beauty of nature as a backdrop.”

It’s Thursday night at the Rosewood and huddles of women wrapped in dresses tight as sausage casings circulate around the lobby. A steady flow of sky-high stilettos and colorful minidresses come in the front door. All head to the dark barroom to the left of the entrance. By eight P.M. many are paired up with younger men. After a drink or two, couples move away from the bar, getting cozy on benches by the fireplaces or under blankets and heat lamps on the deck.

Many attribute the bar’s crush of singles to area matchmaker Amy Andersen—a self-declared “love concierge” and the founder of Linx Dating—who first helped designate the bar a singles’ destination.

Sipping a soda before one of their Thursday-night “meet-ups” at the Rosewood bar, Andersen’s business partner, Nina Ericson, describes the origins of Cougar Night. Ericson—a 50-year-old lawyer turned life coach—goes by the Twitter handle @DrDate2soulmate and often meets Andersen’s clients at the Rosewood spa café. She tells me it all started when the local venture capitalists wanted to find somewhere to go for drinks after work. Men make up 89 percent of venture-capital-firm partners, according to a 2011 survey by the National Venture Capital Association and Dow Jones Venture Source, and a demographic of mostly male, wealthy, well-known businessmen began reliably showing up for happy hour. Thursdays were the most consistent night and colleagues from up and down the road congregated in the comfortable bar overlooking the Santa Cruz Mountains. “Soon, women interested in the V.C.’s started coming,” says Ericson, “and it just turned into a crazy night.”

The Silicon Valley scene is unique. “On the East Coast it matters if you come from a good family or went to a good school,” Ericson continues. Here, not so much. Instead, she says, the venture capitalists who frequent the Rosewood worry about being wanted for their money. The women, on the other hand, tend to be assertive without the ability to turn it off. “They have a tough time being women,” she explains. “Most are very successful, and to succeed in corporate America you have to be strong. That’s fine, but guys might want to hire them, not take them home.”

So Andersen and Ericson set out to solve the problem. With its growing popularity, the Rosewood bar was the obvious setting. Four years ago, Andersen hosted her first “Link and Drink” event at the hotel. The announcement came in one of her seasonal newsletters, “Dating Confidential,” in 2009. She counseled the men beforehand to change out of their baggy Palo Alto polo shirts and exercise pants, to dress up, and put their best side forward. After further advising clients to “bleach your teeth” and “spray tan,” she invited them to the Portico patio at the newly opened hotel. It would be the first of many events at the hotel. Thus, the Rosewood scene—and its accidental by-product, Cougar Night—was born.

The next morning, I meet Andersen at her office, a few miles away from the Rosewood, in the Allied Arts Guild in Menlo Park. The 36-year-old is the perfect face for a high-end dating service. Her bright-blue eyes pop out between thick rims of onyx mascara and impossibly long black eyelashes.

She does not advertise her dating service. Because her clients are high-profile, they do not want to be seen to be using a matchmaker. “It’s a little bit underground,” she says of her business. “It’s not available to the masses.” With other shops in the arts village ranging from the Royal Bloom Boutique to the Barn Woodshop to the Portola Art Gallery, the name Linx Dating would presumably stand out. But Andersen stays incognito. Nestled among the cluster of low ivy-covered cottages with rows of flower beds in between, Andersen’s suite is camouflaged behind a jewelry-and-gift storefront. She shares space with a designer friend so her office is not visible to passersby.

In the back room, Andersen has set up a full silver tea service with cheese and crackers, apple slices, red, white, rosé, and sparkling wines, and ornate goblets in which to serve them. Her fastidious presentation matches the flowery style of the furniture, the plush couches and candle-covered counters. Andersen is wearing a black chiffon dress and has her hair up in a formal chignon with blond curly tendrils hanging down in front. She expertly navigates the back garden in black stilettos as she explains how her services work.

Andersen says she is now advising about 1,000 clients, many of whom work near or on Sand Hill Road and socialize at the Rosewood. She charges $500 for the initial screening, usually performed by Nina Ericson. “A lot have been incredibly successful because of their analytical minds,” Andersen says, “but women don’t want to be out with a cyborg.” If they make it past the screening, clients can choose four different premium memberships: silver, platinum, V.I.P. 1, or V.I.P. 2. Silver costs $20,000 and comes with eight introductions to potential mates. Platinum costs $30,000 and consists of 11 introductions over two years, plus date-preparation techniques, date coaching, wardrobe advice, and dinner recommendations and reservations. V.I.P. levels 1 and 2 are price-upon-request services for clients who have long lists of must-haves; in these cases, Andersen does her recruiting on Facebook or in a “nationwide” search. There are few successful Palo Alto engineers who have not received a Facebook-friend request out of the blue from Andersen. She is constantly trolling. “I use Facebook a lot,” she says. “I can announce as a status update that I am searching on behalf of this client.” She says that, in reading the 13-page applications of the Silicon Valley guys who hire her to meet someone, she finds so many who want Einstein-meets-Heidi Klum (the former being far more plentiful in Palo Alto than the latter) that she has assistants on staff to search social media for any likely possibilities.

While Andersen sees clients of all ages, her business colleague Nina Ericson sees both sexes but has the majority of the older female clients. “If it’s an older woman, it helps them to see someone who’s been there,” says Ericson, who has been divorced. Before she sees them, prospective clients will fill out an initial form describing what they are looking for and what level of service they want. The men she meets are often awkward engineers. “There has always been that part that is really wealthy, like crazily wealthy They have engineering backgrounds without great social skills,” she says. “They are not the C.E.O.’s, who can date up a storm, and they are not great at presenting themselves, but they are brilliant.” Most of her male clients have worked on Sand Hill Road or near it for most of their lives and still act like high-school nerds who have no idea what to do with women. Like Andersen, Ericson often encounters men who think they can engineer the perfect wife. “I have a lot who say, ‘I want a 105-pound Olympian, Ivy League–educated triathlete,’ ” she says. “They are not going to find that on Thursday night at Rosewood.”

What began as a Silicon Valley spectacle—a very low benchmark in an area where most nights out involve pinball or PlayStation—has accidentally become one of the hotel’s defining characteristics. Zagat was the first reviewer to assign the cougar description to the hotel bar, says Michael Casey. A simple Google search of the property’s name brings up Yelp and TripAdvisor headlines such as dreamy beds and cougar nights. There is even a Twitter feed dedicated to the scene, @OnlyOnSandHill, featuring the Sand Hill lobby bar as background. One Yelp review screams, “I hear cougars hunt in these hills!” The reviewer goes on to say, “If you’re a young lad who likes older women, this is the place for you.”

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As another Cougar Night nears its end, Andersen’s meet-up crowd has outgrown the bar and spilled onto the outside deck, where pockets of women surround engineers ebullient with the newfound attention. Even after Rosewood expanded the bar area and added more than $100,000 worth of equipment to make more bar food faster, on this night, squeezing past scantily clad bodies is still a feat. Conversations that once stalled awkwardly at six P.M. are flowing fast. Tipsy programmers are chatting with frisky cougars about companies they have helped build and the ones they’ve witnessed going bust. Handshakes are heading toward hook-ups as day turns to night. “Things happen at warp speed here,” says Andersen, looking out at the crowd. “Here, an I.P.O. is old news before it even happens.” What about Cougar Night? She shrugs. “It’s starting to become younger,” she says. “Now everyone’s out looking for a sugar daddy.”