The Breakup Artist

“The only thing that made me sad was remembering how much I loved Michael Goldenthal in high school and how much he didn’t love me,” Maira Kalman says impishly as she describes illustrating Why We Broke Up, Daniel Handler’s new novel about adolescent ardor and angst.

For the book, published by Little, Brown, Kalman painted pictures of curios that include bottle caps, a box of matches, a stained dish towel, a protractor, a condom wrapper, an egg cuber, and a jar of chestnuts. In fact, she depicted every item hoarded by Handler’s brokenhearted protagonist, an obscure-movie fanatic named Min Green, over the course of Min’s tumultuous relationship with Ed Slaterton, cocaptain of the Hellman High School Beavers basketball team and cad extraordinaire.

Why We Broke Up begins with a thunk, as Min deposits her box of mementos on Ed’s doorstep. What follows is an epic letter from Min to Ed that she left with the box, a letter in which she revisits episodes from the dawn of their love affair through its demise, and the role the fateful objects played in their erstwhile romance.

Kalman, who regularly contributes cartoons to the New Yorker and was recently the subject of a traveling museum survey organized by the Institute of Contemporary Art in Philadelphia, first partnered with Handler on the picture book 13 Words, which came out in 2010. That story is attributed to Handler’s alter ego, Lemony Snicket, who, in Handler’s words “would never be at something like a high-school basketball game and would be more likely in a parasol-factory fire.” While Handler wrote the story for 13 Words before enlisting Kalman as its illustrator, for their latest book, Handler began by asking Kalman what she wanted to depict.

“It was a real roll of the dice, because she likes to paint everything,” the author explains. “I had no idea what she was going to give me. I thought she would say, ‘Freud!’ or ‘these boots!’ or something.” When Kalman decided she would rather stick to rubber bands and ticket stubs and other odds and ends, however, Handler sought to produce “a story in which ordinary things would become beautiful and wondrous,” as they do in Kalman’s paintings.

Beyond their ability to find the extraordinary in the ordinary, Kalman and Handler share another trait, one that is particularly fitting for this collaboration. They’ve both saved their old love letters. “They are fantastically passionate, and I put them in a nice group in a box,” Kalman says of the romantic epistles she recently dug up. “I am imagining my children will read them one day—but maybe that’s not a good idea.”

As for Handler, he fondly remembers one of the many amorous missives he has saved, written by a girlfriend on all of the airsickness bags she could nab on a plane. “It was,” he recalls, “something like 20-barf-bags long.”