Cindy Chupack turns comedic gaze to marriage and domesticity

Author Cindy Chupack.
(Jason Merritt / Getty Images)

Cindy Chupack has built a career chronicling single life as a writer for TV shows such as “Sex and the City,” in relationship columns for Glamour and O magazine and in her collection of essays, “The Between Boyfriends Book.” Now she’s turned her comedic gaze to the sometimes difficult subjects of marriage, domesticity and infertility with “The Longest Date: Life as a Wife” (Viking: 224 pp., $26.95). “My favorite line in the book would have to be ‘Happily ever after is the epitome of lazy writing,’” Chupack says. “Every fairy tale ends that way, and it’s barely the beginning.”

You’ve written so much about single life. What made you want to write about marriage?

I worried when I married that it would be the end of my writing career. When we got married I was 40. I was wishing for five years just to be a couple, but I thought we were too old to do that. It took us such a long time to have a kid that we got those five years — and then some. The book is about what I learned in those five years and what was surprising to me about marriage, what was humiliating, what was tragic, what was funny.

Writing about an ex is one thing, but is it difficult to write about a marriage or trying to have a baby when you’re in the middle of it?


Writing about a marriage instead of dating is very different. I think women and people in general who are more discreet than me don’t necessarily talk about it. You kind of close ranks when you get married. There’s this fear of saying anything negative. There’s much less honesty about what can be hard because it feels a little bit disloyal.

Your struggle to have a baby is a focal point of the book. You even include a chapter about your miscarriage that is written by your husband, Ian. Why did you do it that way?

It’s hard when you’re finally ready to have a baby and the world isn’t ready for you to have one yet. I’d had friends who’d had miscarriages and I said I was sorry, but I had no idea what it meant. It was something that affected me more than I realized. When I got to that part of the book I didn’t know exactly how to write about it. Ian was able to articulate what was so difficult about it earlier than I was.

Your book addresses concerns that are relatively new for women — delaying marriage and family for careers, being the primary breadwinner.

We have the careers we always wanted and then it’s too late to have kids, or we make more than our husbands — these are all luxury problems, I know. I feel like you can have it all, but not in the order that you originally thought and not all at once. I felt very satisfied having done a lot of the things I wanted to do before I had a kid, and I know that’s probably the price I paid and why it was difficult to have a kid later. But I love that I got to travel a lot. I love that I earned enough to buy my own home. My mom never did that. I have no regrets about the order in which things happened.

You call these “luxury problems,” but do you think there is a tendency to dismiss women’s concerns this way?

I may be trying to beat people to the punch because I’m used to that backlash, I’m sensitive to it. I remember feeling, in the baby quest, that there are so many things that make it seem like it isn’t the biggest problem, but the thing is it’s your problem, it’s your horror show.

What do you see as the legacy of “Sex and the City”?


I feel so proud to have been a part of “Sex and the City.” I was 34, and I felt a stigma of still being single. The show’s popularity made being single fashionable. It is actually a fun and vibrant and crazy and sometimes heartbreaking but ultimately amazing time in a woman’s life. It was really comforting to know that those questions of friendship and romance and heartbreak and romance were so universal. It’s sad to me when the show gets marginalized. It wasn’t just a chick thing — it was important.

You’re adapting “The Longest Date” for television. What can you tell us about it?

Jake Kasdan [of Fox’s “New Girl”] is directing. I’m doing it with 20th Century Fox and Fox TV. It’s very close to the book, but it’s a fictionalized version for television. I found that very freeing because in some ways you can be even more honest behind the veil of fiction.