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The Between Boyfriends Book: A Collection of Cautiously Hopeful Essays

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Cindy Chupack takes a hilarious look at love, dating-and not dating-in this witty, truthful and utterly charming book. Tackling topics such as "sexual sorbet" (the first man you sleep with after a breakup), "the VISA defense" (the claim, usually invoked by men, that 'I paid, therefore I am innocent') and "eggsistential crisis" (a panic attack, common among women in their late thirties), The Between Boyfriends Book is as reassuring as that late-night post-date phone call to a best friend. It says: you may be single, but you are not alone.

"Oh, how I love this book! I laughed out loud again and again. It hits such an intimate and true chord, it's painful actually, how insightful Cindy Chupack is. Every woman who's been through the dating miasma must read it."
- Julia Sweeney

"Cindy Chupack is funny about single. Very funny. And smart. And sympathetic. And empathetic. And helpful. And the stories in this book are really horrible in a great way."
- Delia Ephron

162 pages, Paperback

First published August 5, 2003

24 people are currently reading
1472 people want to read

About the author

Cindy Chupack

14 books35 followers
Cindy is the author of The Between Boyfriends Book - A Collection of Cautiously Hopeful Essays, a New York Times bestseller that has been translated into nine languages. In addition, she has written humorous essays about dating and relationships for O, The Oprah Magazine (where she had her own column called “Live Your Best Love Life”), Glamour (where she had a column called “Dating Dictionary”), Harper’s Bazaar, Allure, People, Self, Real Simple, Entertainment Weekly, Slate and the New York Times. Her new comic memoir, The Longest Date - Life as a Wife, was released by Viking in January 2014 and is currently out in paperback.

Cindy Chupack has won three Golden Globes and two Emmys for her work as a writer/producer of ABC’s Modern Family and HBO’s Sex and the City. Several episodes she penned -- Little Bo Bleep (Modern Family) and Evolution, Attack of the 5'10" Woman, Just Say Yes, Plus One is the Loneliest Number, I Love a Charade, and Splat! (Sex and the City) -- were individually nominated for Writer's Guild and Emmy awards.

Other TV credits include Everybody Loves Raymond, Coach, and the hour-long romantic comedy anthology series Cindy created for NBC called Love Bites (all eight Love Bites episodes are available on Amazon).

Her first screenplay (the adaptation of Nick Hornby’s novel, How to Be Good, with the late, great Laura Ziskin producing for Miramax) made the Black List for Hottest Unproduced Screenplays of 2008.

Cindy grew up in Tulsa, Oklahoma and received a journalism degree from Northwestern University, then moved to New York City to work in advertising right out of college. She sold her first humorous essay to a women’s magazine in 1990, and the piece was spotted by a TV producer who encouraged her to pursue comedy writing, which she’s been doing ever since.

Cindy lives in Los Angeles with her husband, their daughter and their St. Bernard rescue, Tink. Tink made Cindy realize that she was, in fact, a dog person, and that "conversion" inspired her to write and direct the award-winning short film, "Whose Dog Is It Anyway?” starring Sarah Paulson.

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284 (29%)
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Displaying 1 - 30 of 107 reviews
Profile Image for Kathi.
237 reviews70 followers
December 2, 2019
That was SO god-damn funny! Absolutely hilarious with an irresistible dose of self-irony. I found the book after my weekly sports course on the shared book shelf (or rather, the book found me, because what are the odds of it having found its way into my arms - for free!!!), even though I would definitely NOT have taken it with me if it hadn't been for my friend who advertised it as the next classic-to-be, and the fact that even after a short glimpse I could already say that Cindy Chupack doesn't take anything she writes seriously. Or so I hope...Considering it's from 2003, the book has really aged quite well because apparently and thankfully, men and women never really change in how weird they are when it comes to relationships. The book is fantastically delightful in that it tells so many funny anectodes from the author's life, that I really laughed out loud several times while reading. And I never do the LOL thing usually, even though I have to say that I really needed the cheer-me-up! The plane chapter was the best thing I've read in a while, and it's sad that I have to say that about something that is featured in a book about dating tips. Will this book help me, or anyone for that matter, finding their true love by succeeding in dating? I sure doubt it! Thankfully, that wasn't the reason I read it, but for anyone who does or is planning to after seeing this sophistacted cover-art and most professional review, and thinks, hey, finally I've found a solution to my never-ending state of being single: nope, you haven't. Don't expect anything else than the author's personal life in this "novel", because I can't say it's about much else. There are even some chapters about her life in L.A. which I honestly say I didn't care for AT. ALL. But, as far as the book goes in describing her personal dating experiences, it was amazing; I honestly think that this makes the book even better than if it had been purely about helpful dating tips instead of making fun of itself. While I do think that some tips were meant to be taken seriously (I cringed very hard through some parts), I can only say that I'm not sure it's a good idea to follow advice given by a woman who has apparently dated approximately 500 men and as to the date of the book, still hasn't found someone she's truly happy with. So yes: better to take that advice with some grain of salt, unless you want to end up the same way (which is apparently married according to her Wikipedia, but not the point of my argument since she had to go through an alarming amount of dates to achieve that) (jesus christ, this woman is (or was?) SO picky! And SO exactly the kind of woman that men are complaining about. But you know what, it was still so relatable, because aren't we all exactly as annoying sometimes? COUGH COUGH). There's just one minor, but really annoying setback to the title of this book: as it states on the blurb "It's called this, so men will know you're available" Oh my goodness, you can't imagine the horrors of reading this book publicly on the bus and subway. Better to hide yourself in a cave while doing that. Not only did I meet the very-likely-future coworker of my coworker-friend who gave me very weird looks (nice to meet you, sir, oh and do you remember how I beat you at Bowling back then? Hahahaha), no! While I was leaning against the subway "wall", the guy opposite of me kept shaking his hair from this side to that side (he had quite longish hair) and it was so irritating! Men, if you see someone desperately trying to cover up the book's title with their hand, that doesn't mean it's an invitation to look at the book even more! I'm just glad I was finished with the book very quickly and didn't have to endure any more of this shit. But apart from that: super-entertaining book, definitely much more entertaining than my review (I gave up on trying to do it justice because it's impossible), and I'd recommend this book to everyone, no matter if you're already married, a teenager who has just started the horrors of high school, gay, an old crone on your deathbed, a prison inmate or even worse: A GUY (I'm just kidding), every single (and taken) one of you would enjoy it, I'm sure. You can't even be mad at the book for some of the many, many stupid things that are being said in there, since the author so obviously claims that she has no clue about dating and considers any kind of advice given by her a piece of fiction, that you just come to enjoy the laments of a crazy person (I mean this in the best way). Is it sad that I enjoy books like this one that don't really have ANY kind of literary value whatsoever more than some highly celebrated works of fiction? Maybe. Very probably. But you know what, I'll admit to it loudly and proudly; just don't expect me to wave this book around in public, pleeaase.
Profile Image for Manik Sukoco.
251 reviews28 followers
January 1, 2016
Here's a lovely short, funny book that any woman who has dated past the age of 25 can relate to.
I found myself alternately nodding in agreement, shaking my head ruefully, and laughing out loud. I zipped through it in about two hours and enjoyed it very much.
I suspect if I were still single I would feel heartened by these humorous essays. As it was, they left me feeling part of a larger group of women who have struggled with the harsh realities of dating. And, of course, mirthful from laughing so much.
I recommend this book for any woman who has ever tried to find The One post-college (especially if that quest continued into her thirties, and most especially if it continued into her thirties and she's a professional, career woman).
Profile Image for Samantha.
531 reviews1 follower
September 9, 2012
I was extremely disappointed with this book. I first heard about it when I was reading a post on the website thesinglewoman.net I thought it was going to be a hilarious book as so she described, but soon enough I was becoming not only really bored of it, but I had no idea what the author was talking about half the time. Yes, in some ways I took a few things out of this book, but for the most part I am glad I went to a thrift store (Half Price Books) and picked it up instead of paying full price for it. I may possibly pass this book on to someone else and get their opinion, but it will more than likely just be thrown into a box.
Profile Image for Roberta Decenzo.
122 reviews1 follower
January 29, 2021
This is not my usual read but Cindy Chupack’s writing is both insightful and hilarious. It isn’t really so much of an advice book as it is a series of essays on her personal experiences and observations while dating. She brings humour to the table in places where stress and heartbreak can make it rather hard to remember to laugh. It is rather comforting to know someone as beautiful, funny, smart, and famous as Cindy Chupack has had the same difficulties and experiences and she reminds us that we are all in the same boat, or, at least, aren’t the only ones who have had these experiences
Profile Image for Delphine Coles.
117 reviews6 followers
October 3, 2022
Maybe is the fact that I am 27 years old reading this and the author is like 40, but I just couldn’t relate. I had to force myself to get through the book and thought the author was whiny and annoying.
Profile Image for Jessica.
329 reviews10 followers
May 1, 2018
I tend to gravitate towards essays when I need something light to go between books. Some of the stories were bubbly and funny and others veered a bit to hard into the clichés but overall okay!
Profile Image for Shannon.
131 reviews103 followers
April 11, 2015
I did not think I would like this book. At all. But it was a book club pick so I went ahead and read it. The book is a homerun. Chupack is so accurate with what singles go through. And the book is very funny. I'd definitely recommend it for the ladies that are between boyfriends. I was happy to see that she has a new release coming out in Jan 2014 too!


If interested,I wrote a more comprehensive review over on the blog: http://readinghaspurpose.blogspot.com...
4 reviews2 followers
July 1, 2017
I absolutely love this book! Though Sex and the City wasn't my favorite TV series, I enjoyed many of the episodes that Cindy wrote - so, I was drawn to the book to see if some of her comedic flair was also infused in this book. To my delight, it was! (FYI: This book has nothing to do with the SATC series.) I couldn't put this book down but appreciated the short length of each of the essays, in case I only had a few minutes to spare to read. I've passed this book along to several girlfriends, as well - whether they're in relationships or not.
Profile Image for Heather.
28 reviews
November 14, 2021
This book had me cracking up from beginning to end, I even read parts of it to my 74 yr old mother and she also thought it was hilarious.

Unlike the SATC book by Candace Bushnell this book had a continuity to it that flowed nicely. Some of the chapters were SATC episodes so they weren't fresh to me, but I can't fault the author for that.

I rarely buy books that I've read from the library but I bought this one.
Profile Image for noa.
66 reviews2 followers
December 31, 2020
Rating: 3.5/5
bite-sized chapters that read smoothly, definitely outdated but still funny at some points, lots of witty/funny/clever commentary on dating experience balanced with wise funny points, fun and quick and smooth read
Profile Image for Hayley Mears.
46 reviews1 follower
November 20, 2020
Loved! Even though written several years ago, the dating observations are still relevant (and funny) today!
Profile Image for Amanda.
666 reviews
January 1, 2021
I can’t believe it took me so long to find this book. It’s like reading long list episodes of SATC. Absolutely loved it.
Profile Image for Kristen.
594 reviews
November 27, 2022
Meh, this was ok. Some stuff didn't age very well since it was written 20 years ago.
Profile Image for Marca.
322 reviews39 followers
January 16, 2016
Kunagi lugesin "Seksi ja linna"-nimelist raamatut Candace Bushnellilt, kaanele oli Carrie pandud, aga sisu oli seriaalist üsna erinev (kui mitte öelda täiesti erinev), raamat millegagi meelde ei jäänud. Wikipedia kirjutab, et see raamat sai seriaalile aluseks, küll vist ainult sellega, et peategelane kirjutas "Seksi ja linna"-nimelist kolumni - muid kokkupuutepunkte eriti ei ole. Tegelikult uurisin ma C.Bushnelli ja "Seksi ja linna" seose alles praegu välja, peale seda kui raamatukogus jäi näppu veel ühe "Seksi ja linna" autori raamat "Meeste vahepeal".
Tolle raamatu autor on hoopis Cindy Chupack, Wikipeedia andmetel "Seksi ja linna" (ja minu meelest üsna maotu komöödiaseriaali "Kõik armastavad Raymondit) stsenarist ning produtsent. Lugema asusin eelarvamusega (kaanel ei olnud Carriet vaid hoopis joonistatud kingad roosal taustal), kuid tegelikult oli see raamat hoopis paremini kirjutatud kui Bushnelli oma. Ma ei saa öelda, et see oli hea raamat, pigem hea halb raamat nagu Nirti kodumaise Kintz Kintzbergi meestesaagat nimetas. See Cindy kirjutab mõnusa eneseirooniaga, toob nutikaid võrdlusi ja paneb naerma isegi minu, kellel tema kogemustele (sain aru, et tegemist enam-vähem biograafilise teosega) midagi kõrvale panna ei ole. Sisu ise on muidugi täielik naistekas - mehed ja kuidas nendega hakkama saada. Sisaldab igasugu feministe vihale ajavaid tähelepanekuid, mis osalt on õiged, osalt huumoriga võetavad. Pidevalt tabasin end mõttelt, et nii oskuslikult kirjutav inimene võiks ju midagi muud kirjutada püüda aga Cindy kirjutab ka sellest teemast raamatu lõpus. Kuidas sa satud Hollywoodi glamuuri keskele ja mandud - kaalukamad unistused põrmustuvad pinnapealsuse all, sest seda hinnatakse, see toob raha sisse. Kurb tegelikult, samas hea, et niigi läks, sest "Seks ja linn" seriaalina ei olnud nii rumal midagi, igatahes parem kui paljud teised naistele suunatud seriaalid.
Teine asi on see, kuidas inimesed asjadest aru saavad. Minu raamatukogust laenatud eksemplar oli näiteks alla joonitud. Keegi oli endale elutõdedena ära märkinud laused "sa võid olla söömata. sa ei saa olla oma kaalule mõtlemata." Hmmm...ma tõesti loodan, et see joonija endale sellest raamatust elutarkusi ammutada ei püüdnud.
Äkki peaks naisteajakirjadel, -raamatutel ja -filmidel ka mingi vanusepiirang olema? Et nende juurde ei satutaks väljakujunemiseas vaid pigem kibestunud keskea(eelikuna)lisena, kes mõrult irvitades tunnistab, et osalt see elu nii naeruväärne ongi.
Profile Image for Charity.
60 reviews5 followers
November 10, 2007
I really enjoyed reading this book. I read it in a day, half of it while I was sitting at the cafe in the bookstore, working on something else, supposedly. It is really quite funny. In terms of it being "cautiously hopeful," however, I would have so say that overall, it was much more cautious than hopeful.

Many times while reading it, I felt like I was watching a Sex and the City episode, and I mean the part of the series before everyone started getting married and having babies (definitely my least favorite part of the series was that part towards the end where the women's lives all "come together"). This makes sense, of course, since the author wrote for that series.

I think my favorite essay is the one about the long string of bad dates, and Chupack's hilarious attempts to number them, counting flings with an ex as only half a date. Her essays often sound familiar in sometimes embarrassing, sometimes exasperating, but always entertaining ways. While the stories she recounts are comforting in a way, the book as a whole doesn't really encourage those who are "between boyfriends," but also doesn't really send the message that you're ok on your own. I like the fact that the book does not succumb to cheesy and cliche "everything will be ok" advice and/or support, but I would have liked a little more confidence and sassy-ness, and a little less cynicism.

I doubt I will read it again, but it was really fun the first time.
Profile Image for Sara.
326 reviews5 followers
May 14, 2012
I chose this book as a "palate cleanser", if you will, a tart taste of lemon sorbet after plowing through 800 page King novels and murder mystery thrillers, and as such, The Between Boyfriends Book served its purpose. The author, Cindy Chupak is one of the writers for Sex in the City, a well written and entertaining series on television and in two movies (so far), and I certainly don't doubt her talent as a writer and keen observer of the human condition in the 21st century. Ms. Chupak also seems to have had first hand, real-life experiences as a single woman in the big city, enough to back-up her observations. Her intelligence and wit comes through in her essays which are clever and entertaining, occasionally thought-provoking, but ultimately light-weight. The book doesn't pretend to be more than it is, so it is not disappointing, so much as unsatisfying. If you think of the author as being something of an athlete in her field, this book is like a casual jog around the block; it fulfills the requirements of movement, but one gets the sense the author isn't really trying and is using only a small percentage of her talent. I don't begrudge her that, but I would really like to see a serious all-out effort from her because I think she's capable of so much more.
Profile Image for Angie.
89 reviews46 followers
July 4, 2014
The Goodreads synopsis really sums it up well when it says "...as reassuring as that late-night post-date phone call to a best friend. It says: you may be single, but you are not alone." It's true, this book really felt reassuring as you made your way through each chapter/essay laughing and thinking about how it applied to your life. I mean there are some ways I couldn't relate, seeing as she's a bit older and living in an entirely different city with an entirely different lifestyle, but there were a lot of ways it did relate to my life as well.

Mostly, I like her frank and honest way of pointing things out to you and making you think about it from a new and more logical angle. Sure, it's hilarious that it happened like that-but what was your role in it? How did you help this come about? Whether it's good or bad.

This book will keep you laughing through the pages, both at her quick wit with which she writes, and as you listen to her painfully embarrassing stories of good-dates-gone-bad and cringe at how familiar it all sounds. I highly recommend it if you like matter-of-fact writing, and especially if you are currently between boyfriends.
Profile Image for Rosa.
76 reviews6 followers
November 24, 2007
A couple of the essays are cute. Most are crap - Men stink, men can't commit, it's always the man's fault, we don't need men, here's how to catch a man, etc.

Chupack should partially held accountable for why women have eating disorders (she devotes an entire chapter to how she lost 10 pounds in a week on the lemonade diet. She writes about the difficulties of fasting humorously, but in the end, she notes that she kept 5 pounds of it off. Way to encourage healthy body image and healthy habits), why women think career success goes hand in hand with sure singledom, etc. I could probably relate better if I were older and more alarmed about being unmarried. Instead I'm irritated at how simultaneously empowering and enfeebling these essays are.

Carries some entertainment value, like Sex and the City, but also rather annoying, like Sex and the City.

As for "what I learned from this book": If I'm in my late thirties and single, never let myself publicly write about being in my late thirties and single.
Profile Image for Marsha.
Author 2 books40 followers
April 18, 2012
This is a book for the lovelorn, the lust filled and those who have nearly given up hope for a husband and/or kids. Did I state “nearly”? Ms. Chupack believes it is possible to climb back into the saddle after you’ve been thrown. But she also thinks that one needn’t climb back on so hastily, at least not when you want to sample the other cowboys out there. This isn’t a self-help book about how to get a man and keep a man. While there is romantic advice, it’s given more from the wry point of view of a survivor than the desperate damsel eager to land a husband. Funny, witty, and dry as a martini but more refreshing than freshly squeezed orange juice, Ms. Chupack has written a fine little books about geeks, nerds, losers, weirdoes and scoundrels and how long you should wait before taking them to bed.
Profile Image for Jasmin.
48 reviews1 follower
August 26, 2018
Gekauft hatte ich das Buch, weil ich alles, was mit SATC zu tun hatte, regelrecht verschlungen habe. Zu dem Zeitpunkt war es für mich eine Ansammlung witziger Anekdoten und gut gemeinter Ratschläge.

Nach dem jetzigen Re-Read blieben mir andere Dinge in Erinnerung. Die Autorin bezeichnet Menschen mit Behinderung als Zumutung, unterstellt Stripperinnen mit Geschlechtskrankheiten infiziert zu sein und verbietet Männern nach traumatischen Ereignissen (hier: ein Einbruch) zu weinen oder sonstige Gefühle zu zeigen.
Eine Stelle, an der die Autorin und ich den Schock teilten: Männer, die lediglich mit ihr befreundet sein wollen. Cindy Chupack stellte schockiert fest, dass diese Männer allesamt homosexuell sein müssen. Ich stellte schockiert fest, dass es Menschen gibt, die mit so jemanden befreundet sein wollen.
Profile Image for Karschtl.
2,256 reviews61 followers
September 6, 2007
One of the script writers for "Sex and the City" wrote her own book, similar to that one by Candace Bushnell and very SATC-ish.
As it says in the undertitle it's a collection of colums/essays, first published in women magazines and all dealing with men, women and their relationships. More precisely: how to end a relationship or how to deal with being dumped. And, most importantly, how to prepare for the men to come.

The idea I liked best was: after a crappy date women can go to the "Getaway Bar", meet fellow sufferer and talk about their experience. Additionally they can treat themselves to some good food and drinks. Fabulous idea!!

Nice book for everyone who ever wondered how Carrie's colums would be like in the complete version.
Profile Image for Rochelle.
Author 4 books7 followers
March 4, 2008
I had expected a lot more from a famous "Sex and the City" writer. Reading the book was like watching an episode of the notorious show, however the voice of Ms. Chupak was not as endearing as the familiar first-person of Carrie Bradshaw. I tried to imagine Carrie talking, but that didn't seem to work either. The chapters were too short and far too shallow. I felt like Ms. Chupak wrote this book while waiting at an airport for one of her many bi-coastal flights as she bounced between NY and LA. It seems like a notebook was not at hand so she decided to write her "novel" on a cocktail napkin. A chapter on each napkin, probably only on one side.

Save your money and borrow this one from a friend or the library.
17 reviews
September 30, 2013
I started reading this book not knowing that the author was a writer for Sex and the City. Since SATC is one of my all-time favorite shows, I became very excited to read this and I was not disappointed. I had previously read the Sex and the City book and was disappointed in how boring it was compared to the show. This book is exactly what I thought Sex and the City would be like. You can really tell that Cindy Chupack related her personal experiences to her writing on the show. It brought back all the memories of my favorite episodes and I couldn't believe these things actually happened! A great read for any SATC superfan or someone that likes to read about the good and bad of relationships.
Profile Image for Beth.
857 reviews46 followers
May 12, 2013
Here's a lovely short, funny book that any woman who has dated past the age of 25 can relate to. Despite not being currently single, I found myself alternately nodding in agreement, shaking my head ruefully, and laughing out loud. I zipped through it in about two hours and enjoyed it very much.

I suspect if I were still single I would feel heartened by these humorous essays. As it was, they left me feeling part of a larger group of women who have struggled with the harsh realities of dating. And, of course, mirthful from laughing so much.

I recommend this book for any woman who has ever tried to find The One post-college (especially if that quest continued into her thirties, and most especially if it continued into her thirties and she's a professional, career woman).
Profile Image for Catherine.
57 reviews
September 15, 2007
There is of course some hilarious terminology coined here, by one of the writers and exec producers of Sex and the City, and some heart - but I remember feeling a bit saddened by some of these non-fiction stories from her life. Maybe because despite the title, you got the feeling the author didn't have that much hope for herself at this point in her life. Either way I'm a fan of her writing on the show, her column that once ran in Glamour, and Oprah geek that I am - am thrilled that she is now a monthly contributer to O magazine. It's a good book to fill those small pockets of time you have for reading.
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