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.
Once you had Carrie’s story down, how did you go about figuring out the rest of the stories to dovetail together?
I don’t remember how the high school theme emerged but we had Miranda dating the doctor and it felt fun to have her start competing with the cheerleader. There’s even a moment with the two of them by their mailboxes where we tried to make it look like they’re by their lockers.
With Samantha’s story, you can see the slightly flimsier connective tissue. The Soho House had just opened in New York when we were doing that episode and one of our writers, Amy Harris, did a hard hat tour of it. She was one of the early members, it was the hottest summer ever and it had a pool. We liked that story — that this was a place Samantha wanted to get into and she’d have to lie to do it.
The Soho House is a great space and gave us so much production value, just to be there in that pool, on that roof, with those views of Manhattan. I still remember all the girls hanging out by the pool, in their swimsuits. We ended up doing a lot of work at the Soho House… it was a place we used to do some writing and we even screened this episode on the roof.
I will never forget the Soho House moment with Kim Cattrall as “Annabelle Bronstein” when she fluctuates between accents and then flounces out in her netted shawl. What memories come to mind when you think back to writing and shooting that scene?
Kim is an amazing comedian and it was fun to let her do that, to let her be on the back foot because that doesn’t happen very often for Samantha. I think it was fun for Kim to be able to play that kind of moment where she’s really in over her head.
That was the kind of thing where you can write it and hope it's funny but the actor makes it work or not work. There were so many times when we would be casting guest actors and you’d feel like, “Oh, this scene doesn't work at all.” Then, the right actor would come in and it would be really funny or feel really right. As a writer, you're so grateful when somebody just gets it and makes it work. That was a pretty genius scene on Kim’s part.
Did you get any heads up that Annabelle was going to be returning for And Just Like That, all these years later?
(laughs) No but I was really happy to hear that, happy to know that it remained in the zeitgeist.
Carrie had a slew of short-lived memorable romances, David Duchovny in this one, Timothy Olyphant, Bradley Cooper briefly, Justin Theroux twice! Did you have a favorite of those brief relationships to write for?
Ron Livingston (Jack Berger) had such a great comedic presence. I feel for him, because it feels like people still blame him for breaking up with Carrie on a Post-it.
But that banter — when I got to write the one where she meets him [“Plus One Is the Loneliest Number”], it was just really fun to write banter between Sarah Jessica and somebody who could keep up with her wit and sense of humor. When we were first thinking about Ron, our original intent was somebody like Sarah Jessica’s husband Matthew [Broderick]. He’s just so witty, they're such a great match, and both in the same field. It seemed fun to have a writer who could be Carrie’s contemporary.
You really do root for those two until it all goes south! I was initially a Carrie and Berger fan…
Me too. I really enjoyed that we always made it a horse race, unless we already knew in advance their arc was going to be something funny — like we knew how it was going to end with John the politician. We always tried to bring in a man who could be a viable alternative option to Big.
You know, Aidan was supposed to be one season and then there was just a huge push. People sent tiny little furniture chairs…
Wow.
There was a big fan push to bring him back. We loved him and he was so good with her and it was such an interesting contrast to Chris Noth that it took on a life of its own. That happens sometimes, the chemistry is so good you want to keep it going.
This makes me think of Dr. Robert Leeds (Blair Underwood) and Miranda having their first kiss in this episode. How much of his character was already a planned arc and how much of it was a wait-and-see with their chemistry?
I feel like we knew where we were heading with Miranda, that she was going to end up with Steve. It started with that TV show she was watching [Jules and Mimi]. I had been watching a lot of British television, and there was a show called Bob and Rose that I loved...I just kept finding myself in love with these British shows. Dr. Robert came out of that world and that got her to him, as this hot guy in her building.
I feel like they could have ended up together if we wanted them to. I hate to say that for David Eigenberg because I love David Eigenberg…
Everyone, to this day, has their opinions on who should have ended up with who. What were some of the biggest debates in the writers’ room when it came to the men in these women’s lives?
It was really between Aidan and Big. That was the biggest one and it was right up until the end, because there were some writers in the room who felt like she shouldn't end up with anyone, that shouldn't be the ending for our show. That was a big debate … had he changed enough? Were we going to believe that he was good for her in the long run? How [do we] redeem him in the eyes of people who we had basically turned off him?
But in retrospect, Michael Patrick King was there from the beginning, and I know he loved Chris Noth in the pilot. It felt like that's where she had to end up, there was such a nice arc to the whole series, being with him.
So you were a Team Big person?
I was Team Big but I understood the worries and I think I tried to alleviate them or at least argue on his behalf that he had changed.
I wrote you this in my email but the ending scene of “Boy, Interrupted” always gets to me so much, when they’re at Stanford’s prom and Carrie is dancing by herself and we hear the voiceover, “So, maybe it won't look the way you thought it'd look in high school. But it's good to remember love is possible. Anything is possible. This is New York.” What memories come to mind when you think back to writing that scene?
I had been thinking about when I reconnected with that boyfriend from so long ago … I realized that part of the appeal of being with someone who knew you back then was that you were still very hopeful, wide-eyed and hadn't gone through the ringer with relationships. It kind of takes you back to that feeling that anything is possible. I think I was always somehow optimistic and would try to contribute the possibility of a happy ending. I think that’s why I was always on the Big ending train.
I’m so glad you said that because I was going to ask you if you’re a Carrie, Miranda, Charlotte or Samantha. This makes me think you’re a Charlotte but I don’t want to project an answer.
It depends if you would have talked to me before my last breakup or after.
It fluctuates!
It definitely fluctuates! I actually always felt that. I always felt like it was kind of a cycle that you go through as a woman, where you're very hopeful and wide-eyed like Charlotte — that's the beginning of any relationship — and then you kind of get in your own way like Miranda does, and then you are like, fuck it when it ends, I'm gonna just sleep around, I don't need men, I'll just use them for sex. And then at some point you're Carrie, trying to just make sense of it all.
P.S. After our interview, Cindy shared some more details via email with me that she remembered, including the fact that it was her high school yearbook Carrie was flipping through in “Boy, Interrupted.” Some of her best friends’ photos are on the page — and that’s Cindy under the name Sabrina Wright!
“I think the fact that I was able to sneak in a little celebration of my girlfriends from high school was an Easter egg I left for my future self and for my friends, because friendship was the heart and soul of the show, and it’s still the heart and soul of my life,” she wrote. “Men have come and gone, but friends are forever.”
(On the topic of friendships, her and her real-life David Duchovny are still pals to this day.)
Loved hearing the story about Cindy's high-school boyfriend and getting permission to use his story for the episode!
I love this, Thea! Tons of new info for me, even as someone who wrote a book about SATC. :)