Second Marriage: How It Can Benefit From the First


Whether or not you know her name, you probably know her work.  Cindy Chupack is a Golden Globe- and Emmy-winning writer who has worked on HBO’s "Sex and the City" and ABC’s "Modern Family."  Chupack most recently worked on a new television series to air next year on HBO called, get ready for this . . . "Divorce," also staring Sarah Jessica Parker.  She is also the bestselling author of The Between Boyfriends Book: A Collection of Cautiously Hopeful Essays.

Chupack has written about her own divorce for The New York Times, and she draws on her personal experiences for her television work.  Her latest book is about Life After Divorce, as in, what happens when you fall madly in love with the right person, marry and try to have a child?  The Longest Date: Life As a Wife is now available in paperback, and is a great holiday gift for anyone newly married.  I caught up with Cindy in Los Angeles to talk about marriage, and divorce, and remarriage.


Wendy Paris: You've been married, divorced and remarried, and written about all three states.  Many of us going through divorce hope that having been married once will make us better partners in a second marriage, or improve our ability to choose the right person.  Do you feel that’s true in your case?

Cindy Chupack:  Yes, and this is part of what my book deals with—the expectation and the reality of marriage.  For better or worse, if you’ve been divorced, you’ve seen the reality of marriage.  Maybe not the best version, but you’ve learned what you need in a marriage, what was missing and what you want the next time around.  I think you’re a more educated shopper, if you will.

Also, it makes you really think about the next time around. How you want to approach it, and how you want to create a relationship that will have a better chance of success.


WP: Can you give a specific example of how divorce made your second marriage better?

CC:  It made me really think about the vows.  Before I met [my current husband] Ian, I went to a wedding with my then-boyfriend.  I realized during the vows, that I wouldn’t be able to stand up and say with complete conviction that he was the person I wanted to marry and be with for the rest of my life.  I realized I wanted to be that sure, to be confident enough to say those vows that I had written before friends and families.

It seemed like, after divorcing, all I was doing was going to weddings.  It was very emotional; I felt insecure, and like I was a dark cloud over these people who were just getting married and so hopeful and optimistic, and hoping to be wed forever.  I started really listening to what people were able to say to each other in their vows.  Before, I’d thought that those vows could be a little annoying; they’d go on forever and seemed corny sometimes.  But I began to really love those personal vows and to see them as an important step in the marriage process.  It became a lot of what I wanted to find in my next, and hopefully final, husband: someone I could honestly declare my love for in front of people who, at least in my mind, had maybe lost faith in my ability to choose well.  I wrote about this in my book. If you can formulate your own vows, write them easily and have a lot to say about this person you love—that’s a good sign.

WP: That’s so interesting!  I write in my book that I proposed divorce while listening to my friend Sara’s husband say his vows.  My ex-husband and I didn’t write our own vows, and I was really aware of that fact later, that maybe I wouldn’t have been able to.

CC:  Ian and I now write new vows to each other every year.  What we did well.  What we need to work on. We write it down and then we read it out loud to each other, maybe on our anniversary, which is in June.  We have them all in a book.  It’s kind of like those Christmas cards that some families put out, recapping the year; that's what we write to each other.  At the end we say, "I would like to sign up for another year."

It’s been helpful.  It’s good to be able to go back and see the challenges we worked on over the years, and what we felt we were good at.  Seeing the challenges gives you more of a sense that you’ll be able to get through the next ones.  It’s a really good exercise to celebrate what you did well.  It’s like a really nice progress report.  You’re noticing.  It’s positive reinforcement.  Maybe divorce taught me that it has to be a conscious decision to stay in the marriage every day and every year.  It’s something you really need to communicate about and keeping working on.

WP: You’ve written about learning that your first husband was gay, and that you felt embarrassed and like a failure for getting divorced.  A lot of people coming out of divorce feel they’ve failed.  How has that feeling changed, now that you’re remarried and have adopted a daughter?

CC: In the moment of divorce, it feels like the end of your story, like a very sad and final ending.  With the benefit of time, I now see that it was the beginning of a really important part of my life.  It was the beginning of being able to focus on my writing career and who I was as a person.

In writing for "Sex and the City," I was able to see that being single isn’t just about waiting to get married.  It can be a really enjoyable and important period of your life.  I bought my condo on my own, which is something you can’t do when you’re married because then everything is a joint decision.  There was lot of fear that buying my own place was the beginning of my spinsterhood, that this was really it; I was buying my own house, and setting up a life in which I’d be single forever.  But it wasn’t.  I was able to create the life I wanted, without a guy in it.  Then I was able to find a guy who could be part of the life I created.

We’re still in the house I bought.  It was a little, "If you build it, they will come."  It was a treat to be able to do these things not the way I’d always imagined with a partner, but in a different way.  There was some kind of joy in being able to do it myself.

Wendy Paris:  I think a lot of us have that fear, “Ugh! I’m going to be single forever!”  How did you meet your second husband?

CC: At the Moth storytelling in New York.  That was one of those things I loved to do, even on my own.  It turned out to be something Ian loved to do, too.  We both told stories through the Moth.  I had told one about my ten-year high school reunion, because it was days before that reunion that my first husband told me he thought he might be gay, and we still went together and pretended everything was fine.  Ian was telling stories also at their story slams.  The night I met Ian I was out with a guy who was just a friend, and I remember thinking, "Why am I with a guy?  I’ll never meet anyone if I keep going out with male friends.”

WP: So you managed to pick up a guy even though you were with a guy?

CC:  Yes, and it’s funny because I always used to imagine my life with whoever I was on a date with, and tell my friends he was The One.  But with Ian, I was sure he was not the guy.  He was tattooed.  Had a motorcycle.  Drank too much.  Did not want to be in a relationship.  Just red flags all around, so I went to work—I was still working on "Sex and the City" at the time—and I said to my friends in the writer’s room, "Do not let me fall for this guy."  That’s when they knew that I would.

WP: What can you tell us about Divorce, the TV show?

CC:  It was created by Sharon Horgan, with Paul Simms as executive producer.  It’s going to be a series with Thomas Haden Church and Sarah Jessica Parker for HBO.  It’s filming now in New York.  I was lucky to be a part of it and be part of the writing room.  There were 10 episodes and we had a writing room in New York for a month.  We broke all the stories and we all went off and wrote episodes.  It was fun to work on something for Sarah Jessica that was potentially the next phase women have to deal with.  It’s a comic look at what it takes to make a marriage last and how hard it is to have a good, easy divorce.

WP: Thank you so much for talking about this.  It's really inspiring to hear. 

For more about Cindy Chupack, check out her website at

* A version of this post originally appeared on Wendy Paris's website,