In this honest, hilarious, fiercely intelligent memoir, journalist Susan Shapiro dares to do what every woman dreams of: track down the five men who'd broken her heart and find out what really went wrong. Between the ages of thirteen and thirty-five, Susan had plunged into love, heart-first, five times. One bad breakup was more hurtful and humiliating than the next.

With insight and daring, Susan chronicles her six-month-long journey back down a road strewn with romantic regret. Although for years she'd blamed her boyfriends for their flagrant infidelity, ludicrous faults, and immature foibles, to her shock she can now suddenly pinpoint the exact moment where she herself screwed up each relationship.

A successful freelance writer living in Manhattan, Susan Shapiro was in the midst of a midlife crisis she called her "no-book-no-baby summer." Married for five years to Aaron, a workaholic TV comedy writer always on the road, she was beginning to wonder if she'd remain book- and babyless forever. Then the phone rang, and it was Brad, a college flame who'd become a Harvard scientist with a book coming out. Susan offers to interview him, and she winds up launching into all the intense, invasive questions she'd always wanted to ask him. To her surprise, he answers them! This ignites a spark that sends her on a cross-country jaunt back through her lust-littered past.

While Brad is still single, she finds that Heartbreaks Number Two, Three, and Four are not. George, a theater professor, and Richard, a music biographer, are happily married with children. Tom, a handsome blond lawyer in L.A., is getting divorced. Just as it's becoming easy to worm her way back into her exes' goodgraces, she crashes head-on with David, a wry Canadian root canal specialist. ("It's the equivalent of what you did to me emotionally," she tells him.) She then gut-wrenchingly relives the agony of splitting up with her first love all over again. Yet somewhere between the tantalizing what-ifs and bittersweet might-have-beens, she finds what she's been searching for all along.

Part relationship manifesto, part confessional, and part valentine to the males in her life she adores, Five Men Who Broke My Heart is for anyone who has ever wondered what became of their first love. Or second, third, fourth, or fifth...

"Shapiro's often funny and always heartfelt recollections of past relationships are so entertaining, it's a shame she doesn't have an endless supply of material....[A] delightfully kaleidoscopic autobiography..." Publishers Weekly

"[Shapiro] merely blazes through each encounter, capturing the flirtatious repartee and humor but glossing over the more complicated motivations and emotions. Amusing — but lacks genuine self-reflection and depth." Kirkus Reviews

This is the funny, intelligent, poignant, and neurotic memoir of one woman's decision to track down the five men who'd broken her heart. On the cusp of forty, freelance journalist Susan Shapiro finds herself in a mid-life crisis: her "no-book-no-baby summer." So when one ex-boyfriend comes back into her life (looking for advice on publicizing his own book, no less!), she's suddenly swept up in revisiting the five men who broke her heart between the ages of 13 and 35. Before long, however, her marriage is starting to show the strain of these past relationships, and she realizes that she's been pushing away the one man who hasn't left her — yet. Is coming to terms with her past in danger of ruining her future?