4 Ways to Make Marriage Funny (And Finish Your Book) From “The Longest Date” Writer Cindy Chupack

Cindy Chupack made the transition from single Sex and the City writer to married author–and made it funny. Here, she talks about the process of writing her new book and looking for humor in “everydayness.”

4 Ways to Make Marriage Funny (And Finish Your Book) From “The Longest Date” Writer Cindy Chupack
[Happy Couple: Gualtiero Boffi via Shutterstock]

In her infamous roman-a-clef, Heartburn, the late, great Nora Ephron wrote this about the difference between dating life and married life:

Cindy Chupack

“One thing I have never understood is how to work it so that when you’re married, things keep happening to you. Things happen to you when you’re single. You meet new men, you travel alone, you learn new tricks, you read Trollope, you try sushi, you buy nightgowns, you shave your legs. Then you get married, and the hair grows in.”

For most people, this doesn’t pose a problem. But for the writer Cindy Chupack, this could have been a career-ending dilemma. Chupack was a writer and executive producer on Sex and the City, and mined her dating woes for material. When she got married at 40, “I thought it was the end of my writing career because I had always written about the quest to find love–a noble and clear goal,” Chupack says. “I didn’t know if there was anything to write about marriage or if anyone could care to hear about it.”

The Longest Date

Lucky for Chupack she managed to make what Ephron calls the “everydayness” of married life really, really funny. Her new collection of essays, The Longest Date, covers topics like Chupack and her husband’s first Christmas celebration (they’re Jewish and became obsessed with the holiday, giant inflatable lawn penguin and all); their ambitious, celebrity-laden dinner parties (Lisa Kudrow makes an appearance); getting a (huge) dog, and even her struggle with infertility, with a trenchant wit and an open heart.

Chupack spoke to Co.Create about how she makes the mundane hilarious, not just in essay form, but also in TV and movies. Though it is just out this month, The Longest Date is already in the process of being adapted for television. We can’t wait to see Chupack’s marital hijinks translated for the small screen.

Read Your Stories Aloud

Happy Couple: Syda Productions via Shutterstock

I’ve done a lot of storytelling. With this book it was how I’d work through a lot of material. It was great to connect with an audience and see what’s making them laugh, to see if you’re feeling self-conscious about certain things. This book is a collection of essays where each stories is an episode that happened. Particularly when we were trying to have a baby, there were a lot of things I went through. Writing for TV, I learned to use my own stories, but with essays, it was fun for me to control the tone, not have a lot of chefs in it.


Save Your Drafts to Use in Different Media

Writing about relationships for magazines was easy and fun, but they want you to provide the reader with a solution or advice–that’s why I loved writing for Sex and the City, too. But when I would write those things I would sometimes save a “book draft”–even before there was a book. Those drafts had a few more tangents and were less conclusive.

Happy Couple: Nejron Photo via Shutterstock

Check With Your Subjects (Especially if They’re Funny)

I run everything by [my husband]. He’s very open and he’s got a great sense of humor, and sometimes credits me with more of a difference than I’m making. He’ll be happy for me to say something controversial or too raunchy or too confessional. He’s supportive of that kind of thing. But I always let him read it first, and would change anything he wasn’t comfortable with. I think, for better or worse, writing about dating is a much easier thing to do, than writing about marriage. When you get into a relationship you do feel loyalty to the other person. They’re not just some disposable guy.

Trust Your Process

Happy Couple with Dog: Phase4Studios via Shutterstock

I used to write at home, but the whole energy of my home changed with a husband, a dog, and a baby. So I got an apartment to write in. I have trouble writing in an office, I need to sit on a bed, and light a candle and have it be quiet, and I need a big long chunk of time. I might only be doing 30 minutes of real writing, but I do a lot of rewriting. I’m constantly going backwards and polishing. It feels like you’re combing this tangle in your hair. I want to get to where I’m not hitting a knot. Sometimes my work is really polished at the beginning and the end is like a first draft because I’m rushing to finish after all that polishing. I can find fault in the end of things. But I can also trust the process. I’ve been doing it long enough that I try to forgive myself.

About the author

Jessica Grose is a regular contributor to Co.Create. She is a freelance writer and editor who writes about culture, women's issues, family and grizzly bears