From “Kissing Jessica Stein” To “Friends With Kids,” Jennifer Westfeldt Fights For Her Films: 52 Weeks Of Directors

by Lauren C. Byrd



Friends with Kids was Jennifer Westfeldt’s directorial debut, but she has fought for the films she’s written as much as any director would.

Westfeldt grew up in Connecticut with a Jewish therapist mother and an electrical engineer father. She attended Yale, where she was part of an a cappella group, Redhot and Blue. She started her career in New York theater and has since starred in over 25 off-Broadway and regional productions.

11westfeldt2 popupJuergensen and Westfeldt

Attending a theatre lab, she met Heather Juergensen and they started developing a series of comic vignettes called “Dating Hell.” One of the stories was about two very girly-girl women who were tired of men, so they decide to date each other. “Very quickly we began to realize that this was more interesting than the bad date stuff. So we put the vignettes together and found we had a play,” Westfeldt said in an interview with The Guardian.

Lipschtick: The Story of Two Women Seeking the Perfect Shade played off-off-Broadway for about a week before it caught the attention of Hollywood producers and studios.

“Everyone just wanted to buy it to give to Cameron Diaz or Jennifer Aniston. We wrote this for ourselves. We were tired of playing the nagging girlfriend, the young mom, the adoring wife, so we created our own,” Westfeldt said.

In fact, a Hollywood studio did buy the rights to the play to turn it into a screenplay. Instead, it sat there for years, unmade. Westfeldt persuaded the studio to sell the rights back to her and Juergensen. They began to raise the money to make the film on their own. “We never even thought of ourselves as writers, much less screenwriters. But just as Jessica and Helen started to take a risk in our story, Jennifer and Heather were like, ‘Ok, we will find the money.’ We would invite people to performances of our screenplay, to try to raise money.”

In 2002, Kissing Jessica Stein finally made it to the screen and to the festival circuit, where it was a success. The film earned her an Indie Spirit Award nomination for Best First Screenplay with Juergensen and a Special Jury Prize for Writing and Acting at the Los Angeles Film Festival. Again, Hollywood producers came knocking, wanting to know about Westfeldt’s next project. 


In between Lipschtick‘s success and conversion to the screen as Jessica Stein, Westfeldt had moved out to Hollywood. In 1997, she starred, alongside now star Ryan Reynolds in Two Guys, a Girl and a Pizza Place. She also met the man who would be her longtime partner and later a TV star himself, Jon Hamm. (Hamm and Westfeldt were together from 1997 to 2015.)

Always a theater actor at heart, in 2004, Westfeldt made her Broadway debut in Wonderful Town. She earned a Tony nomination for Best Performance by a Featured Actress in a Musical.

wonderfultownWonderful Town


In 2004, Westfeldt starred opposite Paul Schneider in How To Lose Your Lover, but it wasn’t until 2006 that she wrote and produced her next project, Ira & Abby. Again, she also starred in the film, alongside up and comer Chris Messina. The film premiered at the Los Angeles Film Festival in June 2006 and was released by Magnolia Pictures in 2007.

Made on a tiny budget, Ira & Abby didn’t break even at the box office, a fact which didn’t bode well for future projects. But for her next project, instead of hosting readings of the script to raise money, Westfeldt finally had a bit of Hollywood cache. She could ask her real world friends—famous actors—to work on her next project for a tiny paycheck.



Friends With Kids is populated by Westfeldt and her then-partner, Jon Hamm, who doesn’t play her partner in the film. Instead, Adam Scott fills that role. Hamm is partner to his Bridesmaids co-star, Kristen Wiig. Maya Rudolph and Chris O’Dowd make up the third set of friends. Megan Fox and Edward Burns the love interests who try to enter the circle of friends.

The director who Westfeldt originally approached for the project, Jake Kasdan, convinced Westfeldt to direct the project herself but appeared on set occasionally to back her up, working as an advisor for free.


Even with her friends pitching in, Friends With Kids almost didn’t get off the ground. Although Westfeldt is as sweet and self-deprecating as her on-screen characters, she stopped at nothing to get her film made. “As I’ve gotten older, I’ve realized diplomacy isn’t my strong suit,” she said in an interview with the New York Times.

“She is directing me, while grabbing a hand-held mirror and putting her lipstick on, talking to the cinematographer, making sure the right vase is on the table, checking with the script supervisor about lines, making sure there’s a location set up for the next day, calling action and then acting in the scene,” Scott said of Westfeldt’s multiple roles on the film.

“The part of all that I think people really don’t get is the superhuman physical, mental, and emotional energy it takes to do this,” Hamm said. “People are going to be naturally predisposed to dislike sisters who are doing it for themselves. And it’s crazy, and it’s not just men; it’s very often other women. There seems to be this expectation of: ‘Hold on, lady. You just stay in your place. Don’t try to reach for too much.’”

friends with kids 5 1024x576Friends With Kids

Westfeldt has a more optimistic view, despite her struggles. “We’re making progress, slow and steady in this world.”

All three of Westfeldt’s movies are attempts to rearrange adult life in a new way. In Kissing Jessica Stein, two female friends are fed up with dating men and decide to date each other. In Ira & Abby, a man and woman whose parents are the epitome of marital dysfunction decide to marry strangers instead.

In Friends With Kids, Julie (Westfeldt) and Jason (Scott) watch as having kids wreak havoc on their friends’ marriages. Instead of ruining a romantic relationship by having a kid, Jason and Julie decide to have a kid together and co-parent while still looking for “that person.” Their friends, of course, see it as a criticism of their more traditional path and expect Jason and Julie to fail spectacularly. In fact, it doesn’t turn out that way. Co-parenting finds Jason and Julie in a good rhythm while still maintaining separate lives, but the problems start when Julie realizes she has feelings for Jason, who doesn’t have them in return.

“I can happily report that all my friends with kids have really responded to the movie and felt it really resonated with them,” Westfeldt said.

Although her films exist in a storied version of New York, much like Nora Ephron’s depiction of the city, the films Westfeldt writes, produces, acts in, and now directs aren’t romantic comedies like Ephron’s. People say and do terrible things to themselves and to people they care about. But in the case of Friends With Kids, it does have a happy ending.

For the past couple years, Westfeldt has spent her time re-immersed in the theater world in New York. In 2013, she starred in The Power of Duff with Greg Kinnear and in 2014, was part of a Public Theater production of The Library directed by Steven Soderbergh and written by Scott Z. Burns. ore recently, she has appeared in TV series including Younger and Girls. She stars in the upcoming film Can You Ever Forgive Me? 

This post originally appeared on Top photo from “Kissing Jessica Stein.”

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