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A Sex and the City writer looks for love

The Between Boyfriends Book is slight, glib, clever to a point, and exceedingly pleased with itself. Its author, Cindy Chupack, is an executive producer and writer for Sex and the City, and—not surprisingly—book and television show share a tone and ethos. I say this without reservation, although I do not watch the program; neither, however, am I impervious to its cultural ubiquity—its catchphrases and antic turns of plot are staples of some of the magazines I read, and I can't count the number of conservative-minded books and articles I've read lately that gesture toward the show as prima facie evidence of our precipitous moral decline. For me, the show's popularity is less portentous, but does raise a set of perplexing questions. To wit: Why does Sarah Jessica Parker, one of the great jolie laides of our time, allow the costumers to suit her up in those fright-night outfits each week? And why in the world do the parents of young girls allow them to watch the show? (I confess to having been a passionate and precocious viewer of Love, American Style, which sent me into romantic reveries of an intensity and specificity perhaps not normal for an eight-year-old. But it is also true that the series did not introduce me to a single euphemism for anal sex.)

Setting these mysteries of the universe aside, we turn our attention to this collection of essays, many of which were originally published in the "Dating Dictionary" column of Glamour magazine. The author's intent is to make us laugh out loud, and she goes at it hammer and tongs, grinding out comic nicknames for her uncountable boyfriends, telling shaggy-dog stories, wheeling her blameless father on stage for a brief, thankless turn as concerned Midwest Dad. She is also deeply dedicated to shocking us. We are intended, I suspect, to gasp in thrilled delight when she counsels women nervous about the potential consequences of a Sex and the City lifestyle to get tested for HIV, "buy a megapack of condoms and get on with your life," and when she reports that her mission to go on seventeen dates before settling down with a new boyfriend "started with a bang. Literally." Naughtiness itself is in the air when she tells us that she has a girlfriend who broke up with a man because "his nose looked like a penis." (This is an objection that may not leave many men in the running for this woman—but that's another matter altogether, I suppose.) Unfortunately for Chupack, none of these revelations shocked me terribly much. In matters of the bedroom I tend to agree with my great-grandmother, late of Saint Patrick's parish, who always maintained that people ought to do whatever they want, so long as they don't do it in the street where they might frighten the horses. What I did find surprising about The Between Boyfriends Book was that mixed in with the megapacks of condoms and the one-night stands were some of the most traditional attitudes about dating I've seen in a long while.

Complaining about the tendency of men to break up with her without much fanfare or remorse, Chupack muses that she would "like to feel like more than simply a notch in somebody's bedpost." The phrase itself is so old-fashioned that I assumed she was setting us up for a laugh, but she is dead serious. She informs us several times that the overall intent of her energetic sexual program is not the zipless fuck of yesteryear; rather, the poor thing turns out to be in search of The One. Chupack is having a hard time finding a husband, she reports—which bowled me over, because it had not occurred to me that she was looking for one. It's one thing to whip off your pajama bottoms, start following the specific and humiliating instructions of a late-night telephone caller, and then suddenly hang up when you realize you're not exactly sure who has called you. It's quite another thing to behave in a way that might entice an investment banker into a lifelong commitment. That men are delighted to have sex with women they barely know but are skittish about marrying ones who offer themselves too freely is a fact of life that women have understood down through the ages. There are wan moments when Chupack cottons on to this, including an italicized bit of counsel: "Dating around doesn't mean sleeping around." In fact, she discovered some benefits to not jumping into the sack on the first date: "I found that it actually helps you slow things down." Alert Stockholm: there's got to be a Nobel Prize for this kind of thinking.

At the heart of Chupack's enterprise is a disregard for men that may suggest why she is striking out so often. The Between Boyfriends Book describes men in a manner so dismissive and callous that had a man written such a book about women, the cries of misogyny would be deafening. But upper-middle-class women hold a lot of power in our culture these days. Still, though, there's one bit of power women will never wrest from men: the decision to deem one group of women candidates for marriage and another group candidates for quick and quasi-anonymous sex.

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Caitlin Flanagan is a contributing editor of The Atlantic. More

Caitlin FlanaganCaitlin Flanagan began her magazine-writing career, in 2001, with a series of extended book reviews about the conflicts at the very heart of modern life—specifically, modern domestic life as it is lived by professional-class women. Flanagan has quickly established herself as a highly entertaining social critic unafraid to take on self-indulgence and political correctness, and her reviews provide penetrating and witheringly funny observations about the sexes and their discontents.

Flanagan's Atlantic articles have been named as finalists for the National Magazine Award five times, and her essay "Confessions of a Prep School College Counselor," which ran in September 2001, was included in the 2002 compilation of Best American Magazine Writing. Her work has also been included in Best American Essays 2003 and Best American Magazine Writing 2003. She is the author of the book To Hell with All That—an exploration, based on her Atlantic articles, of the lives of modern women.

Born and raised in Berkeley, California, Flanagan earned a B.A. and an M.A. in Art History from the University of Virginia. She now lives in California, where she spends her time writing and raising twins.

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