Beyond Sex And The City: An Interview With Cindy Chupack


By Marilyn Friedman


Cindy Chupack has had the kind of writing success most people dream about. She is especially good at transforming her life’s ups and downs into Emmy award-winning magic. She most recently was a co-executive producer on Season Three of ABC’s “Modern Family” and has written for “Sex And The City” and “Everybody Loves Raymond.”


Cindy is also a prolific essayist who has been published twice in The New York Times “Modern Love” column and has written two books. Her first bestselling book, “The Between Boyfriends Book: A Collection of Cautiously Hopeful Essays”, chronicled her post-breakup dating experiences. Her newest book, “The Longest Date: Life as a Wife” was released today by Viking and is available online. “The Longest Date” contains stories about her search for lasting love after her first husband revealed that he was gay. In her spare time, Cindy reads her essays about love and life at LA’s top storytelling venues, such as The Moth and Sit ‘N’ Spin.


On Friday,  January 10th, Cindy will be speaking with master storyteller and Moth Host Brian Finkelstein about her illustrious career. She’ll be sharing tips on how to mine your personal life for literary gold. Get your tickets now before this event sells out.


Cindy took time out of her busy schedule to chat with us about her career and crafting unforgettable stories.


1)  You have written for some of the most beloved TV shows of all time, “Sex and The City,” “Everybody Loves Raymond,” and “Modern Family.” How did you first break into TV writing?


I was living in NY and working in advertising right out of college, and I wrote an essay on spec (a comic essay about living in New York) which I sold to a magazine, and a TV producer saw it and encouraged me to think about sitcom writing.  I moved to LA and took a class for sitcom writing, and from that class I hooked up with a writing partner (the teacher of the class — she asked if I would want to write with her), and together we worked on low rated, short lived shows shows for about seven years until we finally got onto Coach (which at least my parents had heard of), and on Coach we worked with Phil Rosenthal, who created and hired us on Everybody Loves Raymond, and then we broke up as a writing team, so I wrote one Everybody Loves Raymond myself, and I also sold a Sex and the City “freelance” episode to show what I could do on my own, and based on that episode, Sex and the City hired me full-time.


2)  You were a co-executive producer and writer on Season Three of “Modern Family.”  Which family on “Modern Family” resembles your family the most? And were you able to use stories from your own life to inspire the episodes that you wrote? If so, give us an example of something that really happened.


I can’t take as much credit at Modern Family for stories.  That staff was already a super-funny, well-oiled machine when I joined, so every episode I wrote had plenty of other people’s stories in it and a sprinkling of mine. That said, I related to Claire a lot, but I also loved and related to Mitchell and Cam because they were new parents and so was I when I joined the show.


They were all great characters to write for, and I’m proud of the three episodes I wrote — Express Christmas, Disneyland and Little Bo Bleep. Disneyland had a little of me in the high heels, for example. After working on Sex and the City, I tried to wear heels like the characters did, and I look better in high heels (what woman doesn’t?), but I find them less and less practical. On the show Gloria always has heels on, even at home. You have to wonder if she’d be able to get around Disneyland with those, and what if she thought she could, then regretted it, which is what happens to me in heels. That turned into a sweet love story for Jay, when he brings her the fluffy Minnie Mouse slippers, like her knight in shining armor. But even the beats of that story were very much influenced by input from the staff.


3)  Were there any episodes of “Sex and The City” that were based on things that happened in your real life?


Almost all of the episodes I wrote for Sex and the City (and many other episodes I had a hand in) had elements of my real life. The pigeon that landed on Carrie’s date’s head (happened to a date of mine… twice… at C&O Trattoria in Marina del Rey). A doorman telling Miranda that her date wasn’t coming down… ever. I added the “ever” for humor and emphasis, but a doorman did tell me my date was not coming down. In fact it was on Valentine’s Day, and that part I left out because it was so ridiculously sad and hard to believe. The first episode I wrote for the show, “The Chicken Dance,” had a lot of my life in it, which is partly what landed me on Sex and the City because I wrote that as a freelancer.



I had a couple house sit for me in a house I’d bought myself, and they got engaged while staying there. Thus Miranda’s line: “People always say, ‘As soon as you buy a place, someone will propose.’ I thought it would be to me.” I had to write a poem for their wedding, and at the time, the biggest thing happening in my love life was that my boyfriend gave me the pink toothbrush head to his electric toothbrush. (True fans will remember the close up of that detail.)


So many details, large and small, came from real life, from all of the writers’ lives and the lives of our friends and the crew and actors, that’s what made the show so good and singular, I think. Dating a first love who was in a voluntary mental hospital (yes that happened to me and I was in love with him despite that!) became “Boy, Interrupted.”  Having a marriage fall apart even though from the outside it looks picture perfect became “All That Glitters.” Falling for someone who’s taken, and having a book party but no “plus one” to celebrate with became “Plus One is the Loneliest Number.”  I could go on and on with specifics — it was a great show to put all of your heartbreak and hope into.


the_longest_date_bg4)  You have written two books: “The Between Boyfriends Book” and your new memoir, “The Longest Date: Life As A Wife.” How is writing for print different than writing for TV?


The biggest difference for me in writing print versus television is that, for print, I can write as myself.  Writing comic essays is very different from writing for TV because an essay is first person, from the author’s personal point of view.  And it’s hard, especially once you’ve developed your “voice,” for to an editor to argue with your point of view, or change the wording too much, so my published pieces (many of which became chapters in my books) were very much left alone.  Clearly, that doesn’t happen so often in television!


Also, in print, I am not hiding behind fictional characters who have a separate identity and back story and family. Sometimes it’s great to hide behind those elements and tell your stories better than you could yourself — you can write a better ending, or raise the stakes, or embellish the best parts, or watch a fabulous actor say what you only wish you’d thought of saying at the time. But when I write for print, I try to tell the truth as it happened to me, which is especially challenging, but very rewarding when it resonates with an audience.  It makes me feel validated, and helpful, and less alone in the world.


5)  What inspired you to write your latest book, “The Longest Date: Life As A Wife”?


Honestly, I’d written so much about dating (five seasons of Sex and the City, a column in Glamour called “Dating Dictionary,” my Between Boyfriends Book), I was worried that when I got married my writing career (and my story) would be over! That, for better or worse, turned out to be untrue. I found out I had plenty more to say, because marriage is not that different from dating (thus The Longest Date), the story continues, but on this date you can’t just break up with the guy just because you’re tired of hearing him talk about cheese, for example).


I also realized (and say in the book) that “happily ever after” is the epitome of lazy writing. I wanted to write about marriage in the same tone that I’d written about dating, because I felt like there wasn’t as much out there for married people, there’s a closing of ranks — a loyalty switch — that makes you suddenly feel very alone with your problems, which is, I guess, why the adjustments to marriage caught me off-guard. In addition, a baby quest is a special kind of hell that I wanted to write about with humor and honesty just so other couples going through it wouldn’t feel so alone.


6) “The Longest Date” is about some of the more comedic and cringe-worthy aspects of CindyCLargeImageBoxmarriage. How do you take an everyday aspect of being married and make it story worthy? Did you have to exaggerate or enhance any stories in your book? How did you do this?


I think I wrote about all of the toughest adjustments I went through going from single to married. Some of these things will seem very mundane in the abstract (like deciding whether to get a dog, making room for his things in my house, learning that I wasn’t such a great nurturer when he was sick, adjusting to the idea of a man cave). . . this is not new stuff, okay, I know! But for me, the challenge was to be VERY honest and specific and hopefully funny in describing my personal wrestling matches with each of these changes.


In an essay, I don’t like to embellish and I definitely don’t want to fictionalize.  I say, you have what happened. The challenge is — can you make it interesting to a wider audience? Can you remember the important details? Do you know what’s relatable and funny and the best way to describe it to bring the scene to life? Where does the story start? Can you start in the middle? Can you find a crisis point and start there? Will an audience still like you after you admit these things? (In my opinion, if you are wondering that, you’re probably in a good area, because you’re admitting something about yourself that you fear is unlikable, which means it’s something people don’t admit often, and hopefully, when you admit it, other people will relate and be relieved someone finally said it.)


7) You also sold “The Longest Date” as a pilot. Describe the process of converting your book into a script. What were some of the tweaks you made and why did you make them?


I am still working on the script, but the first thing I did was change the names and jobs of the characters (I didn’t want a Cindy and Ian loose out there in TV land, taking on a life of their own) and that was a step toward seeing them not as my husband and I, but as characters. That way I’m free to use all of the great true stories in the book, and others from my life (it will still be infused with my voice and my point of view) but now I can add other stories from other people’s marriages (that’s what a great writing staff is for), and I can embellish, and heighten, and add other characters who have other perspectives on marriage and relationships, so essentially it is born of the book, but it has room to grow.


8)  What do you think makes a good essay and what are you trying to accomplish in your new collection of essays?


A good essay reveals something true about the author — and that truth should be surprising, interesting, funny, heartbreaking, taboo, relatable… or all of the above. And in addition to revealing a truth, each essay (or in my books, each chapter) is still a story. It needs a beginning, middle and end in order to take the audience on the journey to that truth. And by “truth” all I mean is, “What’s your essay about?” There’s not time in most essays for more than one big thought, one big truth. Why are you telling this story, what are you trying to communicate, what’s the big idea — what’s your truth? So in this new book I’m trying to tell the truth about marriage and a baby quest, my truth anyhow, and I hope it will resonate with other people who have been blindsided by marriage, but are still happy to be in one!


9)  What are some of the lessons you’satc31ve learned in your writing career?

Don’t write what you think will sell. . . write what you would like to watch or read.  Write the thing that only you could write because of who you are and what you love and what you find funny.  A GREAT script (or essay or blog) will find its way into the right hands.  If you are getting your work out there and nothing is happening, it’s not a problem with the business, it’s a problem with your work.  Stop complaining about the business and give people stories they will WANT TO SHARE WITH OTHERS.  Because that’s all the business is. A way to share stories with people, the better the stories, the better the business.


10)  What is your writing process like?


It’s pretty much a combination of self-loathing and procrastination. But I’ve been doing it long enough that I have some tricks. This is how it goes lately: Get in a quiet room. Light an expensive candle. (If writing at home or in a hotel, put on sushi pajamas.) Check email and do everything I can possibly do to procrastinate actual writing, like answering these blog questions. Re-read and rewrite what I wrote the last time I sat down to write. Check email. Re-read and rewrite some more. Turn off email. Panic that I’m running out of time to write. Make some tea, which I will forget to drink. Return to computer. Actually write new material. Look at clock and beat myself up that I only did about a half-hour of actual writing in eight hours, but I have polished previous material to a fine sheen. In fact, when I re-read those pages once more, there’s not much I want to change. I don’t feel that way about the new material, of course. Blech. I will look at that again tomorrow. Vow to write more tomorrow. Try to remember that in my career, everything somehow gets written. Sleep. Repeat.


Thanks so much, Cindy! That was fascinating.


Don’t forget to sign up for A Date With Cindy Chupack on Friday, January 10th!