Read The Longest Date: Life as a Wife Online

Authors: Cindy Chupack

Tags: #Biography & Autobiography, #Nonfiction, #Retail

The Longest Date: Life as a Wife

Also by Cindy Chupack

The Between Boyfriends Book: A Collection of Cautiously Hopeful Essays


Published by the Penguin Group

Penguin Group (USA) LLC

375 Hudson Street

New York, New York 10014

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A Penguin Random House Company

First published by Viking Penguin, a member of Penguin Group (USA) LLC, 2014

Copyright © 2014 by Cindy Chupack

Penguin supports copyright. Copyright fuels creativity, encourages diverse voices, promotes free speech, and creates a vibrant culture. Thank you for buying an authorized edition of this book and for complying with copyright laws by not reproducing, scanning, or distributing any part of it in any form without permission. You are supporting writers and allowing Penguin to continue to publish books for every reader.

ISBN 978-0-698-15141-3

Penguin is committed to publishing works of quality and integrity. In that spirit, we are proud to offer this book to our readers; however, the story, the experiences, and the words are the author’s alone.


For Ian, who not only made this book possible, he made it a love story.


Also by Cindy Chupack

Title Page





Are we at happily ever after yet?

When Cindy Met Ian

I was somewhere between a slump and a decision

Get This

Okay, yes, I was married before, and let’s just say it was complicated

The Vows I Read at Our Wedding

As if that wasn’t public enough

Oh, How We Love Bad Boys

When the man in your bed is not the man of your dreams—congratulations!

In Sickness and in Health

My bitchy inner nurse


How much of your life do you have to give up to be a wife?

The First No No Noel

And other traditions you can create or reject as a couple

Now We’re Cooking?

Yes, because chaos loves company!

I Find My Husband Rappelling

Passing the travel test of a relationship

For Richer, for Poorer

“Whose job buys the boob job?” and other riddles for female breadwinners

We’re Having a Maybe!

The trying nature of trying

The Great Escape

Man caves, drugs, and the reality (TV) of marriage

Our Romance Is Going to the Dogs

The story of a rescue

A Fine Mess

Honey, I love you, but the housekeeper has some issues


How I became my own surrogate

Vow Now

Five years in, even my virgin is pregnant

Ian’s Page

Ian takes a page from my book to speak to and for men

And Baby Makes Four

What happens when you stop trying? (Nothing!)

Welcome to the World

Spoiler alert! This story has no ending!



Publication Notes


’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 attitude 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 attractive, 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
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!

Or not.

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 remember 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? Disagreements 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 anniversary we rewrite ours and have the option to sign up for another year—so far so good), and sex? What about married sex?

Oh yes, I am an authority on sex. In fact, I was a sex columnist 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, hysterical truth about the early years of marriage. I certainly could have used some preparation, or at least some commiseration.

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 published 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 prospective birth mothers. Yes, we now had to market ourselves as parents.

I never thought I would be in that position—not the adopting 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 vacation) 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. Bernard I didn’t think I wanted) who had shared five years of adventures (good and bad, large and small) that had strengthened 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.

When Cindy Met Ian

hen I met Ian, I was somewhere between a slump and a decision.

I hadn’t had sex in nine months, which seemed dangerously close to a year. And although I’d racked up a decent (however inexact) number of lovers in the past, not having sex for a year when you’re single feels like it could easily become two years, then three, and before you know it, the only relationships you care about are in
Us Weekly
, and your entire wardrobe is velour.

Part of me thought I should just have sex with someone, anyone, to end my slump before the year was up, but I wasn’t sure if that would make me feel empowered or desperate.

The other part of me felt that you don’t become a vegetarian for nine months and then start eating meat again by buying a random hot dog on the street. Maybe I should wait for a steak, a filet mignon, something delicious, something I might love, since I’d waited so long already.

Of course, calling the sexual blackout I’d experienced “waiting” was romantic semantics at their best. But the way I figured it, I’d been celibate for nine months whether I intended it or not. And nine months of waiting to find a man who was worthy of sharing my bed sounded a hell of a lot better than nine months of failing to find a guy who even wanted to kiss me.

By calling it “waiting,” I felt as if I was reclaiming control of my romantic destiny. As if I’d ever controlled it in the first place. As if anyone could control anything having to do with love. All I could really control was whether I would call my current predicament a slump or a decision, so I went with decision. I
since I’d
almost a year already (see how this works?), I would not sleep with a man unless I was in love. Preferably with him.

It was basically an attitude shift, but an exciting one, because as soon as I realized/decided that I was no longer in a slump, I felt much happier. I started going out more, saying yes more often. Concert on a weeknight? Why not?

That’s how I found myself at a Dave Matthews concert in Central Park with my friend Mark. Mark had tickets not only to the concert, but to the VIP reception beforehand. I remember scanning the VIP tent and thinking
How will I meet a man I might date if it looks like I’m on a date with Mark, who doesn’t want to date me?
And then,
Mark want to date me?

I’d known Mark for years. He was handsome and smart, and nobody could make me laugh like he did. We got along great, we were each other’s default date to weddings, but he’d only ever wanted to be friends. And as much as I would have preferred to believe Mark was gay, he wasn’t. I just wasn’t The One for him, and he wasn’t the type to sleep with random hot dogs from the street, which is why I thought he might be gay, because most straight guys don’t care where they get their meat, but Mark had integrity and valued our friendship, blah blah blah.

In the romantic comedy version of this story, I would marry Mark, the one who was there all along. But I did not.

I also did not marry someone I met in the VIP tent. In fact, as the night wore on, I felt more like a Virtually Invisible Person than a Very Important one. Nobody seemed the least bit interested in me. Or rather, nobody interested me in the least (to reinvoke romantic semantics).

But after the concert (which was a great concert, despite my realization that I would never date Mark or anyone else I might meet while with Mark), Mark and I decided to catch the end of a Moth storytelling event at The Players, a private club in Gramercy Park.

And it was there, at The Players, that I met a true player, Ian.

He’d come with a date, I learned later, but he left with me.

That’s kind of sexy if you’re me. Not so much if you were his date.

If you are reading this, Ian’s date of that night, I owe you an apology. Not for that night—you left early because you had work to do, and with a guy like Ian, you must have known that was the equivalent of a green light. But I owe you an apology because, years later, when we ran into you outside of Canal Jeans in SoHo and Ian introduced us, I was less than attentive, having met one too many beautiful women Ian “used to know.” I think I made a phone call instead of talking to you, and for that I am deeply sorry. If it helps, when I am annoyed with Ian, I think of you as the one who got away.

Not the one whom Ian let get away.

The one who got away
from a life with Ian

By the end of this book, I hope you and everyone else reading this will understand how, at times, a wife might envy the one who got away and still be extremely happy she’s the one who did not.

Now, in New York, it’s perfectly normal to do one amazing thing (like see a Dave Matthews concert in Central Park) and then continue on to another amazing thing (like a Moth event, where people get onstage and share their true, well-crafted stories), as opposed to in Los Angeles, where you have to factor in traffic and a general lack of interest in leaving the house in order to see something mildly entertaining, let alone potentially amazing.

I used to go to Moth events in New York just to sit in the audience, but sometimes I also got onstage to tell stories, so I always knew a lot of people there, and one of those people introduced me to a guy who had won the last “story slam.”

Story slams are the Moth’s rowdier, open-mic storytelling shows that are held in the East Village (as opposed to the main-stage curated events that I had done in the past, like the one that night at The Players). This might seem like a random detail, but I bring it up because although I was “main stage” and Ian was “open mic,” it was probably the other way around, dating-wise.

I remember thinking Ian was handsome, but I guess I was still scarred from the VIP tent, because after the show, when Mark wanted to stay and socialize, I just wanted to go home. It was late for a weeknight, I was tired, and I wasn’t on a date with Mark, so I left.

Ian happened to be leaving at the same time. Only later did he admit this was not a coincidence, that he left because he saw me walk out. (Like I said, he was a player.) He struck up a conversation on the sidewalk, and we talked about storytelling and our jobs, and he said we should go out for a drink, and I agreed and started to give him my number, and he grinned a devilish grin and said, “I meant

He was inviting me out for a drink

Suddenly I was on a date on a night when I had come to terms with the fact that I was not.

it a date? It seemed like a date. We met, he asked me out for a drink. The fact that the date started immediately, instead of two weeks later, after I’d spent fourteen days wondering if he would call, didn’t really matter, did it?

Maybe it did. Maybe I was being picked up. On the street. Like a random hot dog.

In any case, it was happening. We went to a bar that was a block away, because in New York you are always a block away from a bar; that’s another reason why it’s such a great city. And at the bar we talked and drank, and laughed and drank, and drank some more, and then at some point Ian said he was a good poet, and I said I was, too, having written a lot of poetry in my day. But then I realized I was completely outleagued, because Ian said he could improvise a poem on any topic I gave him. So I gave him “a kiss,” and he proceeded to rap/recite a long, seductive, impromptu poem extolling the virtues of a kiss, which, of course, made me want to kiss him, and by the end of the poem we were kissing (me on a bar stool, Ian standing), and it was sexy and magical until I noticed the bartender rolling his eyes.

That’s when it occurred to me that maybe this wasn’t the first time Ian had romanced women with poetry. Maybe it wasn’t even the first time he’d done it at this bar. It also occurred to me that really, I didn’t give a shit.

We decided to go to my apartment, because it was closer than Ian’s. We were going to
apartment, that much was clear. I remember warning Ian that my place was nice (I think I was afraid it would be intimidating or something), and he said, “What the hell? Mine’s nice, too!” and then we started to walk the short walk to my street. Well,
started to walk. Ian was waving down a cab, once again proving that his idea of immediate gratification was much more immediate than mine.

We kissed in the cab, we kissed on my steps, we made out against the wall in my foyer, and eventually we fell into my bed and ended my slump—twice.

And the next morning I woke up in Ian’s arms and said, “Wow, I haven’t done that in a while . . .” and then I realized it was
because I was supposed to be in love with the guy

I had fallen off the wagon, and not with a great guy, but with a bad boy!

I’d have to keep looking. I would continue to sleep with Ian (because—who am I kidding?—I’m not a vegetarian) but I would keep seeking the guy I was going to marry; Ian was not that guy. He told me he wasn’t that guy. He said he didn’t want a relationship, that he would break my heart, that he was trouble.

And it was all a big, fat lie. Ian was the one who decided we should be exclusive. He asked me out for Halloween, and when I told him I had a friend in town, and that the next night my friend would still be in town, Ian realized my friend was a guy (like I said, I was still looking!) and said, “Have a nice time, whore!” and that’s when I knew Ian cared about me.

Ian was the first one to say “I love you,” which came as a shock to both of us. It was after a dinner party we’d thrown together a few months after we’d met (yes, the guy who didn’t want to be in a relationship decided we should introduce our friends), and afterward, as we were cleaning up, I saw a mouse run under my couch. Ian tried to coax it out (which worked—it came out and ran directly into the kitchen
between my feet
to get to another room, the first sign that having a man around to take care of things like mice was not necessarily going to take care of things like mice), but that was so hilarious-slash-upsetting that we left my apartment in the care of the mouse and went out for a drink with two of Ian’s friends, and as they were laughing at the story, Ian looked at me and said he loved me. They didn’t hear him, but who says “I love you” for the first time with other people at the table? Ian did. And it was twice as heart pounding because it was so completely unexpected.

Ian was the one who decided to take the California bar exam so he could be where my career was.

Ian was the one, the day after taking the California bar exam, who said he was going surfing, then surprised me on the beach near my house at sunset to propose, riding a white horse, dressed as a knight. I know that sounds potentially corny, but he pulled it off . . . rented armor, rented horse, and all. In fact, he told me later that the horse had started galloping when he first got on, and his rented helmet closed, obscuring his vision, so all he saw was “dog, sand, ocean, sand.” And then when he finally slowed down and got to me, his foot had slipped out of the stirrup and he couldn’t get the faux armor foot covering back into the stirrup in order to get off the horse and propose. When I saw what was going on, I asked if he needed help, and he said, “No, this is something I need to do myself.” And then a few seconds later, he conceded, “Yes, I need help.” So he rescued me, just like in the fairy tales, but I had to help him get off his high horse. And then the horse—who had once appeared on
Will & Grace
, because in Los Angeles even animals have credits—had to go back to Hollywood, so I got to walk hand in hand with my fiancé/knight-in-shining-rented-armor back to the beach house where I had lived for so long alone, and as neighbors and passersby stopped and stared, I thought, a little smugly,
They said it wouldn’t happen

Ian was the one who wanted to have kids right away.

Ian was The One.

And the rest is romantic semantics. The sweet version of this story is that I had decided that the next guy I slept with would be someone I loved, and he turned out to be precisely that. The salty version is that I did not have the willpower (or sobriety) to wait until I was in love to sleep with someone, but I fell in love with the guy I didn’t wait to sleep with.

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