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  • Written by Susan Shapiro
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  • Written by Susan Shapiro
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On Sale: January 20, 2004
Pages: 288 | ISBN: 978-0-440-33475-0
Published by : Delacorte Press Bantam Dell
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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' good graces, 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…



July 2000

Mr. Studrocket I slipped on the black slingbacks I’d borrowed from my best friend, Claire. The last time I risked such high heels was at my wedding. I tried to walk without wobbling, praying that the added height hid the nine pounds I’d gained since he last saw me. In two decades as a journalist I’d never been this nervous for an interview. Yet I’d never interviewed anyone I’d been in love with before.

I hadn’t seen Brad in ten years. In ten minutes he was coming back to see me. Not to say “I’m sorry,” “I can’t forget you,” or better yet, “No woman has ever been able to replace you.” No, after a decade, Brad was finally seeking me out again—to help him get book publicity.

I pulled a tight black T-shirt over my long flowing Indian skirt, adding silver bracelets. Too Greenwich Village, which I feared I was, but sexy, which I feared I wasn’t. At least I had a tan. Whipping the shirt off, I switched from my sports bra to a black Wonderbra, turning my respectable breasts into major knockers, a Gloria Steinem acolyte suddenly Living Barbie. I would rather be dead than dowdy for this reunion. I tried a tighter black tee—much better—spraying Opium perfume down my faux cleavage. Lining my lips Midnight Red, I caught a spark from my diamond ring in the mirror. My hand was shaking.

Out of the thousands of days we’d been out of touch, Brad could not have picked a worse one to reconnect. Six months before my fortieth birthday, I was staggering through a vulnerable stretch of midlife crises: my “no-book-no-baby summer.” That morning I’d received two faxes. The first, from my gynecologist, summed up results of fertility tests explaining why, for the last year, my husband, Aaron, and I had been unable to conceive a child. My reproductive system seemed to be in fine working order. Aaron’s wasn’t. The problem was his low sperm count and the lack of his sperm’s “motility.” According to the doctor, the medication he’d been taking wasn’t increasing the amount of his sperm or making it swim any faster.

The second letter, from my agent, listed the last five publishing houses that had “passed” on the novel I’d spent five years writing. It felt like she was saying, “The only baby you have is ugly, we don’t want it.”

I threw both letters down the incinerator in the hall, destroying the evidence before anybody else could see it. Rushing back to answer the phone, I thought it would be Aaron, calling from the airport to say his flight was delayed. But it was Brad, the man whose children I could have had twenty years ago, now a Harvard professor, saying, “Hi Sue. I just landed in New York. I have a book coming out,” as if we’d last spoken yesterday. Brad’s timing always sucked. Today it was so bad it seemed destined.

“Hey, that’s great,” I’d said, equally casual, feeling surprisingly jazzed to be on the phone with him. I had an urge to see him in person. “What are you doing for lunch?”

“Coming to see you,” he’d answered, presumptuous as always, though I had just issued the invitation.

“Bring me a galley. If I have time, maybe I’ll write about your book,” I threw out, turning my big date with Brad into a business opportunity to avoid anxiety. Or was it rage?

What the hell did he mean—he had a book coming out. I was the writer! I’d recited Robert Louis Stevenson’s “I Had a Little Shadow” by heart when I was two. My mother taped it, I had proof. In first grade I won an award for filling out the most notebooks in the history of Shaarey Zedek Hebrew School, twelve hundred blue notebooks crammed with Hebrew letters I couldn’t read. In my family, achievement was redemption.

According to Shapiro legend, my father proposed to my mother by saying: “I just got into medical school in the Midwest. You coming or not?” They fled the Lower East Side and eventually settled in suburban Michigan. Of their four offspring, I was the first and the only girl. I was quickly followed by Brian and Eric, both redheaded and freckled like my mother, and Michael, the youngest, whose hair was dark as mine. I always thought the defining event of my emotional landscape was being usurped of firstborn power thrice, by three brilliant science-brain brothers. Picture it: Queen Sheba for seventeen months, then dethroned, dethroned, dethroned.

While I had my mother’s twenty-twenty vision, my brothers were all nearsighted like my father. They wore gold-rimmed glasses with thick lenses and viewed the world as their laboratory. They dissected frogs in the kitchen sink—merrily holding up body parts that pulsated after they were amputated—and kept calves’ esophagi in the freezer and live bees in jars in the refrigerator. (The first to freeze won. Then they’d try to resuscitate them.) By the time I was ten, family dinners were dominated by “The Disease Game,” where one called out symptoms, the other diagnosed.

“Forty-two-year-old Cambodian refugee vomiting blood?” asked my father.

“Schistosomiasis!” jumped in Brian, my oldest, biggest, loudest brother.

“Good! You know more than your old man already.” My father spooned gravy on his steak. “Thirty-four-year-old white woman with perforated uterus.”

“Could be endometriosis,” guessed the middle son, Eric, the diplomat.

“Botched abortion, probably,” weighed in Michael, the smallest Shapiro. “Pass the potatoes.”

I’d eat alone in my pink room, memorizing Sylvia Plath’s Ariel and plotting escape.

I thought I’d found it at sixteen, when I started the University of Michigan in Ann Arbor. Yet on my first day of freedom, freshman year, I gravitated right to Brad, a patronizing, macho biology major.

“Do you have a light?” I stopped to ask him in the dormitory lobby.

He took the Virginia Slim Menthol from my lips and broke it in two.

“Who the hell do you think you are?” I yelled. I’d already decided to be a raging feminist poet. I had no use for this intrusive, oversized prep in a blue-and-gold sweatsuit.

“I’m Brad,” he said. “Don’t smoke, it’s bad for you.”

I noticed his gigantic shoulders. Out of all the first-years, his were the broadest. “So are you,” I said, digging into my backpack for my own match. I found one, lit another Virginia Slim Menthol, and walked away, smoke trailing.

He followed me to my dorm room, where he scanned my schedule (Romantic Poetry, Journalism 101, Modern Drama, Psych. of Deviant Behavior) and declared it worthless. An alliance with a male, fraught with fierce rivalry—what could be more familiar? I declared him worthless and he wrestled me to the floor. I put him in a choke hold my brothers had taught me, never imagining the hold he’d wind up having on me. Or that it would last, off and on, for fifteen years, from age sixteen to thirty-one. The worst years to be off and on in love with anybody.

By the time I was twenty, I’d graduated, sworn off Brad and the Midwest and braved New York City solo. I earned my masters degree in English and toiled, for thirteen thousand dollars a year, as a peon at The New Yorker, eventually finding a way to almost make a living freelancing and teaching. Six months after school ended, Brad surprised me by moving to Manhattan too. Not for me, but for an opportunity to work as co-CEO of a medical research company. When that failed, he decided to get his Ph.D. in biology. Why did he get to publish a book? I didn’t invade his space by curing cancer.

Half linebacker, half bespectacled science nerd (like the males I knew best), Brad hadn’t taken an English class since tenth grade. His letters to me, in his sloppy third-grade handwriting, were hidden in a shoebox in the back of my bedroom closet where my husband wouldn’t find them. The most profound one read, “If I was capable of loving someone it would be you, but I’m not so I don’t.”

During our brief phone conversation, he’d said he was a tenured professor (I was an adjunct) and that he’d wound up selling that “failed” science company for seven figures. He also mentioned (okay, I asked) that he was dating—but not married, engaged, or living with—Kim, a twenty-four-year-old graduate student he could have twenty children with. To make Satan’s Circle complete, my returning WASP-alpha-male-ex had published a self-help book on primal instincts and self-destructive impulses, like the kind I should have suppressed when I told him to pick me up at my apartment.

It could have been worse. I could have been single and idiotically hoping I would end up with Brad, as I had for eleven years after college. What had thrown me was the way he slept with his knees over my legs, locking me in. I liked to sleep as far away as possible, back turned. But the minute he lost consciousness, Brad’s heavy limbs draped over me like an avalanche. I couldn’t move, more physically entangled than I’d ever slept with anyone. Sure that it meant something other than that’s how he slept with women. Plural. Always plural.

Not that it mattered now. I was happily married to Aaron, who didn’t sleep as close but stayed. Aaron was ten years older, four inches taller, twenty times wittier, and a thousand times more loyal than Brad. I was thinking in numbers, subtotalling everything: years, mistakes. Not that I was comparing. This was just a lunch interview and I’d done hundreds. Expertly, on deadline. Hell, I’d taught an NYU class called “Interviewing” and didn’t even need textbooks. When the doorman buzzed, I raced to the intercom, tripped on Claire’s slingbacks, and fell to the floor, wrenching my ankle. I knew I couldn’t handle grown-up shoes, but it was too late to change. I brushed myself off and limped to the door.

Brad walked in and said, “Hi.”

“Hi,” I answered.

We hugged quickly, then I took a long look at him. He didn’t look so hot. He was in khaki pants, a blue blazer, and white shirt buttoned to his neck, stiff. The only time he’d dressed hip was the year I took him to The GAP. I picked out three pairs of tight black jeans and black T-shirts, helping him try them on until a salesgirl yelled, “Only one in a dressing room!” and threatened to call the manager. His brown hair was too short, a crew cut he’d settled on after graduation. I liked him better with the dark, curly, white boy’s Afro I used to run my fingers through. He’d gained weight too. Not fat, but too big. With short hair his features seemed splattered across his face like a platypus—huge ears, nose, brows. Oh no, I still loved him.

To keep my hands busy and my heart from bursting, I handed him things: an anthology that had reprinted two of my essays, my most impressive clips from The New York Times and the Washington Post.

“I found most of these on-line,” he said. “I did a search.”

“You did?” I gave him my two previous books—a poetry collection called Internal Medicine and a humor book, The Male-To-Female Dictionary.

“I’ve already read your humor book,” he said. “It was hysterical.”

“You have it?”

“Amazon.com,” he said.

The hidden perk of publishing: it left a trail that could be easily followed if someone from the past wanted to find you. Or was that the hidden peril?

From the Hardcover edition.
Susan Shapiro

About Susan Shapiro

Susan Shapiro - Five Men Who Broke My Heart

Photo © Dan Brownstein

Susan Shapiro is a journalist whose work has appeared in numerous publications. She's the author of the memoirs Five Men Who Broke My Heart, which was optioned by Paramount Pictures, and Lighting Up, and is the co-editor of the anthology Food for the Soul. She lives with her husband in Manhattan, where she teaches writing at New York University and the New School.


"A delightfully kaleidoscopic autobiography of an impulsive and passionate woman who comes of age with style.... 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."
Publishers Weekly

From the Hardcover edition.
Reader's Guide|Discussion Questions

About the Book

For any woman who has ever wondered what happened to an old flame (or a roaring blaze of them), Five Men Who Broke My Heart offers a hilarious, fiercely frank account of a journalist who did just that. Daring not only to track down her former boyfriends but to find out what really went wrong in each relationship, Susan Shapiro examines a lifetime of love, from age thirteen to thirty-five, and weaves a marvelous memoir from the experience.

The quest began when Susan found herself in an early midlife crisis during what she called her “no-book-no-baby” summer. Her career as a freelance writer was successful, but she had yet to snag a lucrative book contract. Her five-year marriage to Aaron, a workaholic comedy writer, had not resulted in children. Then she got a call from Brad, a.k.a. Mr. Studrocket. It had been a decade since their college romance, and now he wanted Susan to help publicize his new pop-science book. Their reunion makes her want to see all the men from her past, a trek that leads her to discover that in spite of their infidelity, immaturity, and insensitivity, her exes were not entirely to blame for her series of humiliating breakups. Writing candidly of laugh-out-loud foibles and bittersweet what-ifs, she takes us on a mesmerizing tour of the heart.

The questions and discussion topics that follow are intended to enhance your reading of Susan Shapiro’s Five Men Who Broke My Heart. We hope they will enrich your experience of this sparkling memoir.

Discussion Guides

1. Brad's call sparks a host of reactions in Susan–professional insecurity, nostalgia for the past, and a rekindled attraction. How does the reality of Brad measure up to her memories of him? What does their reunion indicate about the nature of a "good match?"

2. Susan's friendship with Claire is a constant throughout the memoir; her shoes almost serve as bookends around the first and last chapters. Are the traits of a lasting friendship the same as those for a lasting romance? Is it realistic to expect husbands to respond like best friends?

3. Was George, the theater professor, a suitable bridge between Brad and marriage? Or did George only reduce the likelihood that Susan would commit to Aaron?

4. Tom, the Robert Redford of Susan's campus, was one of the few suitors her family liked. Are relatives good barometers of matchmaking? Did cross-country distance enhance or defeat Susan's relationship with Tom?

5. Chapter Five ends with several philosophical quotes about love, including Aaron's assertion that "you marry your dark side" and Iris Murdoch proposing that "being married is the best possible way of being alone." Susan also wonders whether her self-sufficiency made her attractive to Aaron. Do you agree with the assertions in those two quotes?

6. What did Richard and his dog teach Susan when she lived with them? Had Richard become more honest by the time they reunited?

7. David writes that Susan viewed him as "just another commodity to be dealt with" and sends a stinging assessment of her attitude toward men. To what do you attribute his perception? Is it ever possible to uncover the facts of a love story?

8. Which of Susan's five ex-boyfriends is the most appealing to you?

9. In the initial portions of Five Men Who Broke My Heart, Susan feels that her life is mediocre compared to that of her siblings and friends. What measure of personal achievement–parental, professional, financial, or otherwise–bears the most significance in your family or community?

10. How does Claire's romantic history compare to Susan's? What do you think might account for the differences and similarities?

11. Discuss the presence of New York as a backdrop in Susan's adult life. What makes it the right place for her now? What is it like for her to journey home? Are these contrasting landscapes significant in terms of how her life unfolded?

12. How would you characterize the storytelling voice of this memoir: humorous, tragic, or something else altogether? What devices as a reporter and book reviewer served Susan well in crafting Five Men Who Broke My Heart? If the book weren't identified as a memoir, would you have called it a novel?

13. Do Susan's five exes reflect any sort of evolution in terms of her emotional growth?

14. If her family applied its penchant for diagnosis to Susan's love life, what terminology would they probably use? What would be the prognosis?

15. Did the men in Susan's family influence her expectations of men later in life? Do Susan and her mother share any common approaches to being a wife?

16. If you were to produce a love chart like the one provided in Chapter Fifteen, what would it look like? Would you be able to construct one from memory, or would interviews and fact-checking be necessary?

17. Aaron and Susan are both professional wordsmiths, but they work in quite different aspects of the industry. What do their varied audiences and attitudes toward work reflect about their personalities?

18. The memoir concludes with several powerful images, including the birthday gift that induces Susan to become more technologically independent, and the visit that makes her realize her aging parents are becoming less independent. What snapshot of love is shared in these passages?

19. The therapist Dr. G. tells Susan: "Love doesn't make you happy. Make yourself happy." Why is this the most important advice of the book?

20. Can you find similarities in Susan's connections with her family and her connections to each of the five men? Have the loves in your life recreated relationships with any of your relatives?

21. With each of the five men, Susan is surprised to discover places she screwed up in each relationship. Can you pinpoint what her mistakes were? In breakups, why is it more interesting and important to be self-critical than to play victim?

22. Susan didn't marry Aaron until she was thirty-five, the age that the poet Rilke recommended writers wed. What are the benefits of waiting to marry?

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