Behind the Episode: Sex and The City's ‘Boy, Interrupted’
Cindy Chupack on writing that David Duchovny storyline, Annabelle Bronstein and the great Big vs. Aidan debate.
The year is 2003, and a single Carrie Bradshaw — fresh off the Post-it note breakup — has found herself on a date with her high school boyfriend. He’s cute, charming, and as she’s swept back up in the unexpected romance of it all, she can’t help but wonder: “When it comes to matters of the heart, did we have it right in high school?”
Elsewhere, teen angst ripples through the streets of Manhattan. Miranda worries she’s competing against a Knicks City dancer for her crush’s affections, Stanford discovers a secret about his boyfriend ahead of the big dance and Samantha feels boxed out of an exclusive club.
There is so, so much to love about the Sex and the City Season 6 episode “Boy, Interrupted,” which offers up delicious comedy (“I was raised in Ind-ja!”), along with those bittersweet, heart-in-your-throat moments that stay with you long after the credits roll. (That ending, with Chicago’s “If You Leave Me Now” ... need I say more?) I got to talk to Sex and the City writer Cindy Chupack all about penning this episode — from the story of Dr. Robert Leeds to the real-life inspiration behind Carrie’s high school boyfriend.
Cindy has won two Emmys and three Golden Globes for her work as a writer and producer on Sex and the City and other shows like Modern Family, Everybody Loves Raymond and Fleishman is in Trouble. She also authored the New York Times bestseller, “The Between Boyfriends Book: A Collection of Cautiously Hopeful Essays.” And I highly recommend her recent piece in Glamour, “He Slept With the Housekeeper, and I Woke Up in Ancient Greece.” Find her at cindychupack.net.
Our conversation has been edited and condensed for clarity.
If I can take you back to the very beginning, I’d love to know the origin story behind “Boy, Interrupted.”
I had a boyfriend on my tenth-grade trip to Israel and it might have been one of the first times I felt like I was in love. He was from Florida and I saved up money to visit him. We got older and didn’t stay together but, many years later, when I was working on Sex in the City, he called saying he was visiting for a while and would love to see me. It turned out he had been in a voluntary mental institution, so I visited him there. We ended up dating again for awhile, and I kind of had all the thoughts that Carrie had in this episode.
I wasn't ever going to use [the story] until later he said, “So, are any of your characters going to date someone who was in a voluntary mental institution?” and I was like, “No, I would never do that.” He said, “Well, you can if you want.” I ran into the writers’ room, [saying] “We can use it!”
How did he feel about having David Duchovny as his fictional counterpart?
I think that’s got to help, right? (laughs)
Did you have David in mind when you were writing this part?
After I wrote the script, when we were dreaming about who would be really great in that part, he was our top choice. It was a pleasure working with him … he improvised a bit, too. He ad-libbed, “It’s a lot better without the gear shift sticking up my ass” after the kiss, which we all loved.