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'Sex' and the single woman

Sunday, February 22, 2004

By Samantha Bennett, Pittsburgh Post-Gazette

Cindy Chupack may have kissed "Sex and the City" goodbye, but she's still voicing the frustration and amusement of single women everywhere. Her anthology "The Between Boyfriends Book: A Collection of Cautiously Hopeful Essays" was published last August, with the paperback edition due in May. Foreign editions are already out in several languages, including Dutch, Italian and her favorite, Estonian.

"I guess these dating issues really are universal," she marveled on the phone from -- where else? -- New York.

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Chupack joined HBO's "Sex and the City" as a writer/executive producer in its second season and has shuttled between New York and L.A. Though she enjoys the bicoastal life and plans to maintain both homes, despite the series ending its six-season run tonight, she finds New York the better town for singles.

"To me, a city where you're forced to run into people, where your apartment is small and you maybe don't want to spend a lot of time at home," affords, almost forces, more opportunities for romance. "You're more likely to get out. Also, New York is more singles-friendly in that married people are always moving out to the suburbs, and new single people are always moving in. L.A.'s not like that. Also, I think you feel less conspicuous being alone in New York."

Chupack, 38, grew up in Tulsa, Okla., and earned a journalism degree from Northwestern. She went to New York and worked as an advertising copywriter for Prodigy, one of the earliest Internet service providers, crafting copy to describe and sell fine chocolates ("the artist's renderings weren't very good"). Granted this glimpse at the future, she quickly concluded, "This is no place for a writer."

So she began writing humorous essays for magazines. That led to television sitcoms, and then to "Sex and the City," the series that followed writer Carrie Bradshaw (Sarah Jessica Parker) and her three closest female friends as they navigated the New York singles scene.

Though Chupack may have raised the single life to an art form, she has not always lived it. An early trip down the aisle didn't work out. But the experience taught her a lesson that mostly keeps a lid on the urgency that can haunt a single woman nearing 40.

"Having been through all that, through a divorce, I have a bigger fear of being with the wrong person than of being alone," she explained. "I try not to let the biological clock thing scare me into being with the wrong person just to have someone.

"When you're older, you know better who you are. But, yeah, everybody has those moments of what I call in the book 'existential crisis' -- when you realize your desire to have children and [your desire] not to settle may be mutually exclusive." But there are alternative options for creating a family, perhaps through adopting a child or marrying a man who has children.

Chupack sees cause for cautious optimism everywhere, even at a high school reunion, which she presents as a chance to catch the "retro Love Boat." Last year she went to her 20th in Tulsa. "The women looked amazing," she said. "The men -- I thought, 'This is where good ol' boys come from': You know, kind of heavy, with the big belt buckles. The women all looked like models." Against her mother's dire prediction, "The cheerleaders seem very happy."

And when the "Love Boat" sinks? She gave the story of her worst breakup ever to Miranda on "Sex and the City." The brushoff came via a doorman, who said the guy would not be coming down. Ever.

"[Women] just want closure," Chupack said. But then, she's had the bad news via a doorman and she's had it in person ("The guy said, 'Let's meet at your apartment and we'll go from there, and I thought he meant go out, but actually ...").

"There's really no good way to break up," she concedes.

Still, that's no reason to be shy. She said her fellow writers describe her as a kamikaze, always willing to throw herself into adventures and take chances. But as she sees it, "part of the job of love is going to involve a crash."

How does a writer for "Sex and the City" meet men? She's tried everything, including online dating, which she described as "the least amount of effort you can spend and still say you're dating." It's kind of a safe, low-stress way to get acquainted, but great e-mail doesn't always translate to great dates. "In some Cyrano de Bergerac way, I guess it should," she said a little wistfully, "but I haven't found that."

Often there's no chemistry, or she encounters something else about a man that brings instant distaste.

"I always discover new deal-breakers," Chupack said. For example, there was the guy who had been to 1,700 Bruce Springsteen concerts. That was his whole life. She fished for other interests. "Do you travel?" she asked. "Well, yeah. To Springsteen concerts," he said. They had no chemistry, and, worse, he didn't get her sense of humor.

Sense of humor is important, because "that's how you get through everything," she said.

The best way to meet people and avoid a total mismatch is to "find things you'll enjoy -- something you'd want to do anyway, like walking your dog or going to a concert or reading. Be in your element." That way, you already have at least one shared interest with anyone you meet. And if you don't meet anyone, you've done something you enjoy and won't feel you've wasted your time.

Chupack believes one of the better ways to meet people is through friends. "I'm a big proponent of having a party for single friends," she said. Just have "a big, fun, classy party," especially for New Year's Eve, invite friends, and tell them to bring their friends.

But how can any man cope with dating a woman who puts words in the sometimes ribald mouths on "Sex and the City"? How can a man relax with a woman who writes about dating for a living?

"It definitely gives men pause," she admitted. It almost scared off the man she's seeing now.

"The day after I met him, I gave him my book, because I was, you know, proud. He told me later that that was a huge tactical failure."

Nobody's perfect. Like the sirens of "Sex," Chupack has friends she can rely on when Cupid gets stupid.

"Always keep your circle of single friends," she said. "Your best friend is sometimes just the last one who's single."

As for the swan song of Carrie Bradshaw, "We talked a lot about what would constitute a happy ending." If Carrie is to remain single, what would that mean? Single and alone? Single with prospects?

"I think we finally decided to go with a hopeful ending," Chupack said.

"I think we did right by her, and I think the way we ended it makes a larger statement about being true to yourself."

And perhaps cautiously hopeful.

Samantha Bennett can be reached at or 412-263-3572.

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