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As much as Melanie fit my preconceived notion of a cougar, the night from that point forward challenged it. None of the other women who approached me (and they always did – I didn't have to initiate one conversation) were nearly as aggressive as Melanie. Maybe they'd toned down their behavior to suit the environment, but I guessed not. The more I watched and interacted with various women at the party, I came to realize that they were generally normal middle-age women who differed from their peers perhaps only in their tolerance for adventure, openness to dating younger men, and willingness to identify — at least for a night — as a cougar. The party may have been successful at pulling back the curtain on relationships between older women and younger men, but it also represented a contrived reality that engendered unfair expectations and shoehorned a whole lot of people into categories where they don't quite belong.
Few women were brave enough to travel alone as Melanie did; most stuck to the side of one or two girlfriends while they worked the room. Only one other broached the subject of sex, but she appeared to be much younger and disinterested in the whole scene. Likewise, only one other woman made as direct of an approach as Melanie, strolling up to my friend and I early in the evening. "Finally, someone more my age," she joked. "They should've checked IDs at the door and turned away all men over forty." She was forty herself, she offered, and lived in Oakland. She'd driven through the tunnel alone earlier in the day and had her hair styled nearby. "It looks good," I noted as platonically as I could. "You certainly don't look forty."
"Thanks, I appreciate it," she replied. "I get that a lot, but I do appreciate it." There was a sweet sincerity to her that hardly shouted cougar, even if she was one of the prettier and more straightforward women there.
Later I met a petite, fashionable Asian woman — in horn-rimmed glasses and straight, shoulder-length hair with highlights — who, sensing I was too young for her, opted to provide dating advice: "Don't go looking for perfection," she said. "You'll never find it. Instead, look for a best friend, someone you love to hang out with." With that she bid me adieu and encouraged me to keep mingling.
I soon stumbled across three friends in their early- to mid-fifties who offered to help me win the icebreaker game — a Bingo-like card labeled with identifiers such as "Has been married," "Reads the newspaper," and the baffling "Has two cats." You were supposed to walk up to people, say hello, and ask them to complete a square for you.
"Hi Nick," one of the women said as all three sized me up from head to toe. "Are you playing the Bingo game?" I showed her my card with only two names filled in. She pulled it from my hands and began to write down her and her friends' names. This left me feeling we'd cheated the system, but mostly flattered they'd even bothered. It was a subtle, old-fashioned form of flirting and proof that not all so-called cougars approach with voracity.
Eventually, a photographer who'd been milling about the room approached me and a few women. When he introduced himself as being with the San Francisco Chronicle, I gulped: Here I was, a married man reporting undercover at a cougar party, and now a fellow journalist wanted to document my presence. He instructed us to look casual as he snapped a couple shots. Not wanting to break cover, I played along.
Then he asked for my name. My nametag already read Nick, so I needed a last name and blurted the first thing that came to mind: a twist on my wife's maiden name of Santora. Just then a woman appeared behind him with a pen and notepad. A reporter. Now I was really in trouble. When the photographer finished shooting and moved on to another part of the room, the reporter approached and directed a question toward me: "So Nick, why do you like older women?" My new acquaintances were still within earshot — maybe even listening — so, in Nick's somewhat cocky tone, I brushed off her question with a non-answer I hoped she wouldn't quote. I roped Paul into fielding her next query and made my escape.
Ten days later, the Chronicle ran both my photo and quote on the front page of the Style section. My turn as undercover cougar bait had come full-circle: not only had I passed for a cougar chaser among the discriminating women themselves, but I'd unwittingly sold my alternate persona to another newspaper. I wasn't proud of misleading fellow journalists, but couldn't help chuckling at the irony of the result. As long as I was part of it, the cougar scene truly wasn't all it was cracked up to be.
By most accounts a highly eligible cougar, Jerusha Stewart has her own misgivings about the term. She happens to be an expert in the field, having authored The Single Girl's Manifesta: Living in a Stupendously Superior State of Mind and starred in twenty episodes of her The Last Single Girls web series ("We pick up the conversation where Sex and the City left off," her web site boasts. Most recent episode: "Dating After 50.")
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