The Longest Date
Life as a Wife
The bestselling author of The Between Boyfriends Book and an award-winning writer for Sex and the City and Modern Family takes a hilarious, heartbreaking look at marriage
Cindy Chupack has spent much of her adult life writing about dating and relationships for several hit TV series and as a sex columnist for O, The Oprah Magazine. At the age of thirty-nine, she finally found The One—and a wealth of new material.
Marriage, Cindy discovered, was more of an adventure than she ever imagined, and in this collection of essays she deftly examines the comedy and cringe-worthy aspects of matrimony. Soulful yet self-deprecating, The Longest Date recounts her first marriage (he was gay) and the meeting of Husband No. 2, Ian.
After the courtship and ceremony, both Cindy and Ian realized that happily ever after takes some practice, and near constant negotiation over everyday matters like cooking, sex, holidays, monogamy, and houseguests. The Longest Date takes a serious turn when it comes to infertility.
The Longest Date is the perfect companion for anyone navigating a serious relationship, be it newlyweds or couples moving in that direction.
I’ve always been a romantic. When I was single, I slept only with men I believed I could marry.
That would be admirable except for one detail: I slept with a lot of men.
A lot a lot.
I’m not going to tell you the exact number because my parents might read this book, and they certainly don’t need to know the tally.
And also, I don’t know it. Don’t judge me.
I was single for a long time. Alcohol was often involved.
I didn’t keep a guest book by my bed, so, yes, some names were lost along the way.
The point is not my incomplete sexual history, okay? It’s the more troublesome issue that every time there was a man inside of me, there was also a voice inside of me saying This might be the man I marry!
Clearly, I knew nothing about the reality of marriage. Or hormones.
I’m not sure which was more dangerous—my casual atti- tude toward sex or my delusions of love—but one led to the other in a decade-long binge of salty and sweet, horny and hopeful.
Finally, after enough relationship wreckage to fill a book (The Between Boyfriends Book), two magazine columns, and five seasons of Sex and the City, at the age of thirty-eight I found a guy I absolutely did not want to marry, and, of course, he’s the guy I wound up marrying.
I’m not saying I settled. I’m saying I met a wildly attrac- tive, interesting, smart, funny guy who had so many red flags—many of which he voluntarily and repeatedly waved in my face—that I told my coworkers at Sex and the City, “Do not let me fall for this one,” and that’s when, they say, they knew that I would do precisely that.
We’d all seen the romantic comedies; we drank the Kool- Aid. Hell, we were making the Kool-Aid. So it was hilariously predicatable that, like every other rom-com heroine, I found my happy ending when I least expected it, music up, wedding montage, cue credits!
Turns out “happily ever after” is the epitome of lazy writing. Maybe fictional characters live happily ever after, but for the nonfictional rest of us, the story continues with a lot more complexity, and in a way, marriage winds up being the longest date ever.
And however much we think we know how to do dating, on this date, you can’t decide not to see him again because you’re tired of hearing him talk about cheese. For example.
You have to try to work things out, or at least appear to try, and as it turns out, I was completely unprepared for this job.
I got married at forty (despite my lobbying efforts to move the wedding up a month so I would still be thirty-nine). I re- member complaining to friends that, because of my age, my husband and I would have to start trying to have kids right away. I sincerely wished we were younger—that we had five years to be just a couple.
And I got my wish. We didn’t become magically younger, but we did get five years to ourselves, thanks to the myriad problems we encountered trying to have a child.
So what did I learn in those five years? And how can I help you prepare for that thing about your spouse that you must somehow embrace because he’s your spouse? (Wanna hear about cheese?) The fertility problems you might face because it took two decades to find a guy to face them with? Disagree- ments about pets, space, houseguests (I think I’m adverse to them because I still secretly feel my husband is one), couples therapy, entertaining together, cleanliness, vows (every anni- versary we rewrite ours and have the option to sign up for another year— so far so good), and sex? W hat about married sex?
Oh yes, I am an authority on sex. In fact, I was a sex col- umnist for O, The Oprah Magazine while we were going through IVF treatments, and I finally gave up my column because sex had become so fraught for me, so synonymous with failure, that I could no longer in good conscience advise women on how to “spice up their sex lives” with porn and lingerie. I felt like a fucking fraud, literally and figuratively.
So, in this book, I wanted to tell the honest, horrible, hys- terical truth about the early years of marriage. I certainly could have used some preparation, or at least some commis- eration.
I also noticed a lack of humor and hope in most of what’s been written about infertility. Women I know— and even women I don’t know—encouraged me to fill this void when they responded so enthusiastically to the first piece I ever pub- lished about the trying nature of trying: “We’re Having a Maybe!” (which is now a chapter of this book).
The one thing my husband, Ian, and I learned from this experience is, never say never. In fact, as I began writing this book, we found ourselves in a craft store buying construction paper for the scrapbook we’d been advised to make for pro- spective birth mothers. Yes, we now had to market ourselves as parents.
I never thought I would be in that position—not the adopt- ing part (we’d always been open to adoption) but construction paper? Really? But our adoption lawyer said our scrapbook should look homemade, so we spent a weekend gluing photos of ourselves (with friends, with family, on holidays, on vaca- tion) onto Easter egg–colored construction paper, which we hole punched and bound with ribbons.
And as we were doing this, as we were making this little Book of Us, I realized we had, somehow, amid the chaos and confusion of cohabitation, built a lovely life together. There we were, page after pastel page, two people (and one St. Ber- nard I didn’t think I wanted) who had shared five years of adventures (good and bad, large and small) that had strength- ened our bond as a couple.
So I’m grateful for those five years, hard earned as they were, and although “happily ever after” still strikes me as the romantic equivalent of the Rapture (sure, it might happen, but let’s not spend our lives waiting for it), I am writing this book for every woman who ever was or will be blindsided by the reality of marriage: to validate and celebrate life as a wife.
"Laugh-out-funny and surprisingly poignant."
"A straight-talking, funny and poignant memoir."
“The characters on ‘Sex and the City’ (for which Cindy Chupack wrote) could never wait to get together and share the most scintillating details of their romantic triumphs and tribulations. Opening Cindy's book is like getting invited to lunch with those women—the details are keenly observed, laugh-out-loud funny and you never want the meal to end.”
“If you need a new best friend—look no further! Cindy Chupack’s wonderful book will make you laugh, cry, and feel less alone.”
“Cindy's essays are dizzyingly good. They're funny, they're meticulously crafted, and you hardly notice she's doing a comedic equivalent of a ballerina's masterful pirouette. I laughed, I commiserated, I wanted more and more. Marriage is laid bare, negotiations, passion, uncertain leveraging, children, dogs and even boob-jobs are all covered with affection and brutal honesty.”
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