Cougar Night in Silicon Valley

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By: Alexandra Wolfe

Thursday nights have become surprisingly popular at a five-star Menlo Park hotel. Two eagle-eyed matchmakers, big tech money, and an army of stiletto-shod women mix and mingle there—all important factors in Silicon Valley’s peculiar mating algorithm.

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.”

 

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.”

 

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.”