Five Men Who Broke My Heart: A Memoir

by Susan Shapiro

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…

Genres: Memoir, Nonfiction, Biography Memoir, Relationships, Humor, Autobiography, Chick Lit

240 pages, Hardcover

First published January 1, 2004

Reviews

[Jeanette · Rating 1 out of 5]

OMG, it barely makes a 1 star.

Honesty now! I only got to page 70 and that was it for me. The only reason I started this book is because I am in a Summer Library Program and I am supposed to read 3 books that have a number in their title.
I'll find others.

This was a tell-all whine from the get-go. And then got worse.

It should have been titled: Five Men Who Had Incredible Luck to Escape.

Someone out there in the book world should have been her friend. And gone on to tell her not to publish this shallow exercise in self-centered arrogant angst.

[Nancy · Rating 1 out of 5]

Use this book to stuff an old mattress. Shapiro didn't do herself any favors publishing this shallow piece. Irredeemable. I prayed for the trees that died for her self-indulgence. It took to the last few pages before she thought of anyone but herself. It brought NOTHING to the reader but an AMAZING desire to start burning books.

Save a tree. Dump this piece.

[Tara · Rating 2 out of 5]

The book seemed like it would be an amusing, chick-lit memoir. Oh, but it was so much more. The author whines throughout the entire book. There didn't seem to be much character growth at all--just a bitter woman rehashing all of her crappy relationships. I finished the book just to see if she learned anything from all of this whiney soul-searching, but I don't think she did. I feel a bit sorry for her husband.

[Elissa Jane Mastel · Rating 1 out of 5]

I read a "Modern Love" piece in the New York Times by Susan Shapiro and I loved it. It was truly identifiable. At the end of the story, it mentioned this book, so I quickly downloaded it hoping it would be more of the same. While the beginning of this book was engaging, it got dull, and lost it's luster. I guess I can't read another 100++ pages about a woman who has so much who seems so ungrateful, who thinks gaining 9 lbs in 20 years is something to be sad about or whines about not having a child. Ugg... whatever. Get some depth!

Hey, I've had my heart broken, I know about those guys, I understand wanting to look and sound a certain way when we see them again, but there's more to it, isn't there?

I dunno, I am 30% through it and putting it down for something more substantial. I thought this would be a fun poolside chick-lit read but it fell pretty flat once I was out of the gate.

[Elizabeth · Rating 3 out of 5]

After having read this book, which contains 1 moderately graphic sexual description, I found it nearly impossible to talk to Susan when I met her at a party. It took me two weeks to be able to talk to her husband again (he was my teacher at the time I read the hot-tub scene) and at least 20 seconds of aimless, vague compliments on her home, food, wine, etc. before I decided not to mention I'd read any of her work. Probably just as well; knowing the real people is a detriment to enjoying the characters based on them.

[Sarah · Rating 1 out of 5]

I really disliked this book. I felt trashy just reading it and found the protagonist thoroughly annoying from start to finish. I would've left her too.

[Sophie · Rating 3 out of 5]

I got to this book from an article the author wrote in a magazine, but I think I ended up enjoying the magazine article more.

The book is about going back and confronting exes, which is probably everybody's secret wish at some point - but there's something in the way she goes about it that bugs me. It's honest, but instead of it feeling like she's putting herself out there it ends up feeling like she's just...hanging out there. You want to admire the author for her bravery, but you end up feeling a little bit sorry for her. It ends up being the experience you're glad you haven't had, but you're eager to see what's become of the person who *has*.

Cons
-the complication of her situation prevents it from being universal and truly resonating with you, so the stories end up being slightly annoying rather than sympathetic
-the writing seems kind of unpolished and unprofessional. anecdotal to the point of being rambly.
-lots of angst

Pros
-fascinating, personal topic for a book
-the colloquial-ness of her tone makes you feel like you're reading something from a friend
-author is brutally honest

[Alexis · Rating 4 out of 5]

I'd like to give this book 4&1/2 stars, which unfortunately is not an option. The title of the memoir could easily make people suspicious that this book may be a ranting diatribe against men, or a weepy revelation of lost love. The book is neither. The memoir is a testament to "applied therapy." Susan Shapiro's writing is extremely sharp and witty. Her self-examination is exceedingly honest and she does an excellent job of examining motivation and perception as it is effected by one's age and memory. I would recommend this book to anyone and everyone.

[Morena · Rating 5 out of 5]

Amazingly readable.

[David Weitzman · Rating 5 out of 5]

Susan is literally bestie! I love her writing so much.

[Kate · Rating 1 out of 5]

You know how sometimes you approach a book (play/movie/etc) with a sense of what it will be like? and that sense is telling you that said book (etc.) will be just the kind of thing you like? But then... it absolutely isn't?
I imagined that "Five Men Who Broke My Heart" would be comprised of serious, professional interviews with past lovers, and that this would be poignant and intriguing, perhaps even instructive. But... it absolutely isn't.
It begins with a chance meeting with a past lover, with whom the (married) author then exchanges a series of vaguely flirtatious e-mails. In describing the situation and her feelings of resentment against this man-- both for his insufficient love for her and for his present success-- she stretches to make it all very funny.
I flipped through a few more pages and then decided to donate the book to the local SPCA thrift store.

[Rachelle · Rating 3 out of 5]

Another memoir on my reading list. I was interested in seeing the framework the author used to explore several decades of events in her life. She had a nice story frame and the narrative was engaging, often hilarious, self-deprecating and raw. While there are other topics that might interest you more than someone's past love affairs, the story certainly has universality. I was struck by her introspection and the revelations that came of her own family relationships. For me, these were the most beautiful moments of the book.

[Marisa Turpin · Rating 1 out of 5]

I initially gave two stars, but in truth, I did not like this book at all. It feels kind of bad to judge a memoir. I mean, it is not fiction, so you are basically judging someone's life -- or at least judging the way she writes about her life. I had a hard time keeping up with the 5 guys, they all seemed to run together, maybe because she went back and forth between some of them. I almost didn't finish it, but pushed through to the end.

[Sandy · Rating 3 out of 5]

It's no surprise to me to see this book rated all over the park... I often wondered why I kept coming back to this one. I'd swing from "Shape Up" to "What the..." I recognized a strong intellect who went to college at 16. Her Dec. birthday should have encouraged another year at home. Ended up rating it in the middle because when I finished her book, I really like her.

[Jen · Rating 3 out of 5]

A freelance writer in Manhattan revisits with the five men of the title. I enjoyed her quest to make sense of her romantic past. It also convinced me that looking up all my old boyfriends is something I'll never do.

[Laurie Smith · Rating 3 out of 5]

Lackluster

This book was ok I would not recommend it. It had its funny moments but overall it was kind of weird. Trying to find old boyfriends just to verify you married the right person???

[Kami · Rating 3 out of 5]

It's hard to rate a memoir well when you don't end up liking the writer much. Well written and in many places very clever and enjoyable. I'd love to write a similar book, or read one at least, about someone who I find more likeable

[Carla Jean · Rating 3 out of 5]

I first bought this after a break up, and although it's not the most amazing memoir I've ever read I return to it time and again. (And not necessarily after break ups, either!)

[Avisha · Rating 5 out of 5]

Re-hashing old relationships for healing purposes can do wonders for a woman.

[Nikki (Saturday Nite Reader) · Rating 3 out of 5]

Fun story. Quick read and would def. recommend as a weekend book!

[Lavanya Sunkara · Rating 5 out of 5]

just met the author last night. She's awesome, so I decided to pick up her work. :)

[Meichler · Rating 4 out of 5]

Really fun memoir of a married woman, in her late 30's/40, who decides to track down the 5 guys who broke her heart. Fun, easy, good writing, and very relatable.

[Karen · Rating 4 out of 5]

Enjoyable! Makes me wonder about some of my exes.

[David · Rating 3 out of 5]

I came across this book on Bookbub and decided to try a little lighter reading than usual. Since I recall reading some of Susan Shapiro's material in The New Yorker and the New York Times and the title was intriguing, I thought I would give it a try. While it was humorous at times and pretty well-written, I am trying to figure out what it was all about. Is the author extremely introspective or doesn't she really have a clue how she comes across? If the former, I'm not really sure what her point was. Perhaps that is because I am not a 40 year old female writer encapsulated in modern New York City. (Nor do I really want to be after reading this memoir.) If the latter, it is easy to see why she has multiple ex's as she comes across as self-centered and self-absorbed to the extreme. Is she parodying herself or does she really not get it? Maybe leaving the reader to judge was her intent, but I'll leave it to someone else to figure out. While there is a certain fascination with such self-indulgence, I think I'll return to other forms of non-fiction that will give me more insight into the human condition other than true love is boring and all women have father complexes.

[Tracy L. · Rating 4 out of 5]

After ending my 20+ year marriage a few years ago, experiencing heartbreak from a rebound relationship last year, and having my college boyfriend randomly resurface in my life a few months ago, I've been digging into the hard work of looking at the common denominator in my relationships--me. This book felt like the same kind of examination and ruminations over the what-ifs and why-nots and what's-wrong-with-me conversations I'd been having with my girlfriends and my therapist.

The dialogue and rehashing of stories with her exes sometimes felt too abrupt, leaving me feeling as if I didn't quite understand what she learned or discovered from her encounters. But, I completely related to the desire to see yourself as the only one wronged or the angst of not fully getting the answer you wanted. The truth is, would any answer help us with closure?

Her honesty and vulnerability about her past relationships and the struggles in her marriage ultimately gave me hope for my own better, although undoubtedly imperfect, relationship to come.

[Laurean · Rating 3 out of 5]

I almost gave up on this book because I am beyond reading the young adult/ "Cosmo girl in the city" genre. I didn't like the protagonist was the problem... She presented as arrogant, self -involved and a pampered fruitcake. Oh, I forgot, flippant and 'petite!' When I got through the cliche boyfriends/ lifestyle in New York, I began to like this book because I felt her portrayal of Aaron, her parents and the insights into her childhood were warm, genuine and caring; finally some feeling for others! I did not appreciate her cavalier attitude toward her many abortions (that is what was heartbreaking) or her need to expose her sacred and intimate marital relations. Not everyone needs to know all the details. Ms. Shapiro needs to read some Jane Austen or Bronte.

[Karen Mckinney · Rating 5 out of 5]

Honest. Compelling. Funny. This book was a guilty pleasure read during my recent vacation and I could not wait to sneak away to read it. The author's funny account of her revision of her history of 5 love affairs that led to meeting her current husband was filled with tidbits about life, relationships, and the reasons why they sometimes do not work. She never throws her ex's under the bus but gives a self reflective account of her own choices peppered with fun vignettes of sex, love and witty dialogue between her and her past paramours. It was insightful and delightful. I truly enjoyed this book and cannot wait for more from Shapiro.

[Irene · Rating 3 out of 5]

(I'm not even sure how I ended up reserving this book at the library. I thought it was recommended by BookPage, but I couldn't retrace a recent review of the book. In fact, I didn't realize the book was from 2004 (and reviewed by BookPage in 2011?)...)

Anyway, I don't read a lot of memoirs, but I went with it... The author ends up painting a very sweet picture of her husband and other family members who didn't break her heart, while at the same time looking back at relationships that were heart-wrenching. It was interesting seeing some places I know written about in the book. At the same time, there's a bit much TMI in the book.

[Cafes and Books · Rating 3 out of 5]

I like this book. Shapiro is as honest as they come. Some reviewers think she is too vain or shallow, but I think every single one of us would be unlikeable if people around us knew everything we thought about, our secrets and real opinions of them. Shapiro's honesty is uncomfortable for her, her husband and family. That is what makes a writer worthwhile. If I published a book like this, I'd feel naked walking down the street. This kind of intense vulnerability and ugliness is what it takes to connect people and make people feel less alone in the world.

[Samantha · Rating 4 out of 5]

I think it's awesome that the author grew up in Michigan and went to U of M Ann Arbor. As far as my feelings on the book, I felt like the book could have been written in a better way, more storytelling. But the author is primarily a journalist, so it makes sense that I read that way. Also, I'm sure most people would think that the story / autobiography I inevitably want to write would read this way, too.