SOCIETY

WAS SHE PRETTY?

SHANDA DEZIEL December 18 2006
SOCIETY

WAS SHE PRETTY?

SHANDA DEZIEL December 18 2006

WAS SHE PRETTY?

A new book plumbs the mystique of women who knew him before you did

SOCIETY

SHANDA DEZIEL

A few years ago, Toronto-born writer/artist Leanne Shapton was living in a new city, London, with a new boyfriend—but she was surrounded by ghosts. “There was evidence of all of his

ex-girlfriends in his apartment,” she says. “There were lots of photographs. And one of his exes was a fashion designer and all of his clothes were done by her—they had a very distinctive kind of cut.” Shapton would stay home during the day and sketch what she thought these women looked like, along with a couple of sentences about the traits that intimidated her and sparked her jealousy. Friends who saw her series of 12

sketches could relate. Seems everyone has a story about their current flame’s ex.

Shapton, 33, interviewed friends and acquaintances on this subject for her latest book, Was She Pretty?, in which men and women obsess over those who came before them. There’s the inane: “Lucy’s ex-boyfriend only dated actresses. It didn’t matter to him if they got roles, but he was happy for them if they did.” The funny: “Milosz scrupulously updated his address book with his ex-girlfriends’ current numbers, even if he hasn’t spoken to them in years.” And the destructive: “Isabelle found a vacation snapshot of her boyfriend’s ex-girlfriend. She ripped it up and left it in a neat pile on his pillow.” All of which are accompanied by Shapton’s simple, evocative drawings.

Shapton, who used to be the art director at Saturday Night magazine, now lives in New York with her boyfriend, James Truman, the former editorial director of Condé Nast. (Truman and hotelier André Balazs threw Shapton a New York book launch at the Mercer Hotel that was attended by singer Bryan Ferry, designer Paul Smith, actor Jennifer Jason Leigh and filmmakers Noah Baumbach and Todd Solondz.) Of course, Truman is in the book too. “I had to go through my own relationship,” says Shapton. “He had some doozies—the Matterhorn of terrifying women.” In fact, Truman helped Shapton come up with the title of the book. She was thinking something along the lines of “What Was She Like?” or “Was She Beautiful?” but Truman offered the more succinct, “Was She Pretty?” “He’s heard it many times,” says Shapton.

What the author found with most men, including Truman, is that they’re more jealous of an immediate threat or of the men who replace them, rather than the ones who came before. And that men’s jealousies come down to about five things. “It’s always, ‘He was rich, he had hair.’ It’s always status, power, sexual prowess, physical ability.” Meanwhile, the number of things that can drive a woman crazy, says Shapton, are innumerable. And the book is made up mostly of women obsessing over other women’s virtues or faults. It’s an exercise that ends up being more about the people in the current relationship, and their own insecurities, and not about the ex at all. “You don’t really know anything about the ex,” says Shapton. “And it was a failed relationship, so it’s nothing to be afraid of.”

Easier said than done. Shapton had one boyfriend who talked about his ex-girlfriend so much, she swore she saw the woman in a bar, even though Shapton had no idea what she looked like. “I said to a friend, ‘I think that’s her, will you go up and see if she went to Brown?’ ” Sometimes you just need to find out for yourself if she’s pretty. M