A Conversation with Cindy Chupack

As most of you know, I love talking with writers and learning about how different people approach and think about the creative process. So when I had the chance to have a conversation with best-selling author, storyteller and Emmy-winning TV writer Cindy Chupack, I thought you might like to hear from her, too.

When Cindy performed in Spark's “Trapped” show, I learned that she was actively sharing essays from her forthcoming book, The Longest Date, at various storytelling series in LA as a way to workshop them (in fact, she used the Spirit of Story site as a guide to finding the best places to read around town!). What a smart, creative way to develop material, I thought. So I encourage you to check out the interview below and glean some of her wisdom!

Cindy Chupack is an author, storyteller and Emmy-winning TV writer whose credits include Modern Family, Sex and the City, and Everybody Loves Raymond. Her first book, The Between Boyfriends Book: A Collection of Cautiously Hopeful Essays was a New York Times bestseller. She followed up with The Longest Date (Viking, 2014), which is a humorous look at the reality of marriage and the trying nature of trying (to conceive, create, adopt or kidnap a baby).


Karin: Tell us about your new book!

Cindy: When I first got married I thought my writing career was over, because all I had ever written about was dating. I was worried there was nothing more to say, because who really cares about married relationships? It took me a while to realize that a wedding was not the end, it was the beginning of a whole new story, a whole other adventure. That's why the book is called The Longest Date. It wasn't that different to write about being married, I realized. You have the same sort of conflicts, you just can't break up.

How is live storytelling different from other kinds of writing you do?

I see first-person storytelling as you connecting with an audience and telling them what happened to you in your own words. Because they're hearing it from you, it feels very different and very intimate. It's more intimate than even writing a first-person essay, because even though that's you and your voice, you're not face to face with the audience, you're not hearing their concern or their laughter or their disapproval. So it's just a different kind of beast. You definitely feel more exposed, but it can also be very gratifying to get the feedback and the community of an audience being with you while you're telling a story.  

It's certainly different from the writing I do for television, because even if I'm drawing from personal experience, it is several times removed once you put it through the filter the character you're writing for. In fictionalizing the story, you're not publicly putting yourself on the line -- you're just using the story, or the experience, or how you felt -- as a starting point. The good news is, then you can rewrite what happened and let an actor do or say what you wish you'd done or said at the time!

What have you learned from work-shopping essays from your book at various storytelling venues around Los Angeles?

I've had people worry that my piece is going to be offensive or seem privileged or seem too harsh, and I can usually sell it with my personality. So I shoot for that now when I write, to get enough of my personality and voice in it that you understand where I'm coming from in the piece, even if I'm not there to sell it myself.

But also I've learned to tighten up jokes and to add more jokes. When you're reading aloud, you sometimes think of something funny off-hand in the pause between lines or in the laughter. I've seen that some pieces are more serious than I realized, and I've learned to be okay with that, to trust that the audience is still with me even when they're not laughing.

And then very basically, when I'm choosing a piece to read from my new book, there are certain pieces I think, “Nah, I don't want to read that one.” And then I think, “Why didn't I want to read that one? Is that one weaker than the others, does it still need some work? How do I make it better so I would want to read it aloud?”

Where do you draw the line when writing about your private life?

I'm pretty open, and it's been an interesting transition to go from writing about dating - which is usually failed relationships or just failed dates - to writing about a couple, which involves my husband also, and what he's open to me saying. I think that might be why there is not as much that's funny or current written about marriage.

There is a kind of closing of ranks once you're a couple that people respect, and I felt like that was a doing a disservice to women and really everybody, because there are still stories, and we still need some help, we still want to commiserate. And I think women (especially storytellers) should be able to talk about marriage in a goodhearted way that makes you (the narrator) equally culpable. It's not about male bashing or husband bashing, it's about laughing at all you go through as part of a couple, and trusting that those experiences and feelings are relatable to other couples.

I've definitely cleared everything I've written with my husband. My biggest dilemma now is just how to talk about what we went through to get a baby, because some day this will all be preserved for our child to read, and I want to make sure I'm writing about things I am comfortable with her knowing.

How do you approach writing a new piece?

One big thing, I guess, is that I always keep the audience in mind. I try to remember... even when I'm writing my book... I try to imagine I'm almost writing an email to a friend or something. I just really try to be myself, and be funny but honest. I think sometimes you forget the audience when you're writing and then you get lost, so I try to think of the audience as a friend, and I try to remember the story I'm telling is for an audience, not just for me.


To learn more about Cindy Chupack, visit cindychupack.com

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