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.”
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 cafĂ©. 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.

“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 cafĂ©. 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.
by Alexandra Wolfe, Vanity Fair | Read more:
Photograph by Justin Coit