Can the Cougar Trend Make This Man Famous?

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Jon Snyder


"Welcome to the worldwide headquarters of the Society for Single Professionals!" Gosse slowly motions his hand outward like a magician or a game show host.

We've just walked the hallway from his living room, through the master bedroom, and into a makeshift office. There are two enormous PCs, piles of receipts, and a map of the SF Bay with the word "Gosse" written in Sharpie on a label covering "San Francisco." An overstuffed bookcase is filled with extra copies of his own dating books. The titles include The Cougar Imperative, The Singles Guide to America, and A Good Man Is EASY To Find: In Southern California. All totaled, Gosse has written eight of them.

A large sliding glass door opens onto a patio, a sunny garden with roses, oranges, and grapes, and a deck shaped like the hull of a boat. He had it built after buying the house 15 years ago. The deck once doubled as a dance floor.

"This used to be a great party pad," he tells me. Gosse's annual Labor Day singles shindig was attended by 150 guests—that is, until his lawyer told him it was a liability. No problem. For Gosse, this stuff has always been serious business.

In 1978, after quitting his job as a Catholic schoolteacher, he founded American Singles Education Inc., which he prefers to call the "Society of Single Professionals" ("It's catchier"). Because he was able to incorporate as an educational non-profit—yep, instructing singles qualified him—Gosse didn't need to worry about revenue. Nevertheless, he maxed out three credit cards to get up-and-running. His best friend said he was crazy. Gosse began hosting meet-ups at a local church, then graduated to nightclubs, and even started lecturing on dating—which he himself didn't start doing until he was 19 years old.

"I was the most chicken guy in San Francisco," he confesses. "I probably wouldn't even be alive right now if the first girl I asked out said 'no.' I probably would've found me a bridge."

The valedictorian of his high school, Gosse always planned on becoming a priest. During his sophomore year in college, he realized celibacy was not for him. From there, the shy-guy graduated to full-scale bachelorhood. He says he was rejected "hundreds of times," but just kept trying. Eventually, he built up the swagger and confidence that emanates from him today. Seriously, you should see Gosse work a room. He shakes hands with everyone, and doles out hugs to the ladies who know him. If any of them were holding a baby, he'd certainly kiss it.

"In psychology, they have a fancy word for this. It's called desensitization," he explains, "Whatever you're afraid of, if you want to conquer that fear, you have to experience it over and over again. So if you're afraid of snakes, you have to handle snakes. If you're afraid of spiders, put a spider on your arm."

The demographic imperative of cougardom began to resonate with him when he was in his 20s. He recalls being a cub to more than a dozen cougars. I ask whether any of these older women ever expected to marry him?

"No, I think they were just looking for young man meat."

On Valentine's Day 1995, Gosse co-founded Americansingles.com, which he says was the second dating website in the world, and the first-ever free dating website. By the time the site was acquired in 1999, they'd collected 250,000 users—a lot in those days. The deal left Gosse flush with cash, which is how he managed to buy a four-bedroom home in Marin, the wealthiest county in California, according to Forbes.

Having established himself as somewhat of a figurehead in the professional dating world, he founded a PR firm. Today, publicity is his main source of income. During our conversations, he namedrops URLs like singlestravelcompany.com and hedonismresorts.com in the hopes they'll make this story and impress his clients.

With a roof over his head, and traction entertaining singles and doing PR, Gosse became his own publicist. He relentlessly hounded the booking agents at talk shows. For years, he pitched himself as the ultimate "American singles guru."

Finally, he wound up on Donahue. But it wasn't until he concocted the idea of hosting a "Flirting Convention" that he achieved the brass ring: An appearance on Oprah.

As it goes for dating itself, persistence wins.

In 1996, he'd started hosting cougar parties. Only back then, he called them "younger men, older women parties." By the time Demi Moore and Ashton Kutcher were making headlines, Gosse was all but ready to pounce. One quick re-brand later, and he was tossing around the word "cougar" as much as possible.

He booked a ballroom at Dinah's Garden Hotel in Palo Alto, California, and crossed his fingers. "I didn't know if 5 or 500 people would show up!" he recalls.

It sold out. And then some.

"These guys were desperate to get in. They were crawling through the bushes!" he says, "We had to turn away about a thousand people."

Persistence wins—unless sometimes, for some people, it doesn't.

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Steven Leckart is a correspondent for Wired magazine. He's also written for Maxim, The Daily, GOOD, and Pop-Up magazine.

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