Jon Hamm and Jennifer Westfeldt (Friends With Kids)
Jon Hamm and Jennifer Westfeldt reunite on-screen for her directorial debut, "Friends with Kids." Reuters

Jennifer Westfeldt -- best known as Don Draper's real-life leading lady -- is perched to become a household name herself thanks to Friends With Kids, the actress-writer's directorial debut. Co-stars include Adam Scott, Kristin Wiig, Maya Rudolph, and her longtime love Jon Hamm.

There's something fascinating about Hamm and Westfeldt together: One of the most desirable and sought-after actors in the industry, famous for playing a dark and complex character with crippling honesty and intimacy problems, has for fourteen years been with a woman the average Mad Men viewer had never heard of pre-Don Draper. They have never married, and they don't have children -- and won't say one way or another if they ever will.

Were it not for Mad Men, the hardworking Westfeld would likely still be the more successful of the two; but these days, she's almost never mentioned (or photographed) outside of the context of her famous boyfrend. A small handful of negative items on gossip sites have painted Westfeldt as needy, in one instance, and over-Botoxed in others. In 2009, Westfeldt talked to New York Magazine about Hamm's sudden rise to fame: I still haven't come up with a good answer to 'He's so hot, how did you land him?' or 'You're so lucky to be with him!' Um, thanks?

It's tempting to think of Friends with Kids as a platform for Westfeldt to address the curiosities about her relationship and her career. The premise unapologetically draws from her own experience as a childless minority among a circle of upwardly mobile, urban-dwelling couples who have started families: Westfeldt told the blog Brightest Young Things that she missed co-star (and close friend) Adam Scott and his wife once they had kids, and admitted to feeling out of sync with [her] peer group.

Friends with Kids is the second on-screen reunion between Hamm and Westfeldt since Kissing Jessica Stein, which Westfeldt wrote and starred in. The couple met while Westfeldt was writing the screenplay, and she gave Hamm a minor part. He appeared again in a larger role in her 2006 follow-up, Ira and Abby, which did not perform as well (financially or critically) as indie darling Kissing Jessica Stein.

Friday's New York Times profile of Westfeldt credits a nepotistic casting coup for helping Friends with Kids make it on to the screen. Westfeldt had a secret weapon: her real-world friends -- famous actors who were willing, just on the strength of their friendship with her and Hamm and their faith in the project, to work for peanuts. The big names -- Hamm's being the biggest -- no doubt helped lubricate a distribution deal with Lionsgate and Roadside Attractions after Westfeldt's directorial debut screened at the Toronto Film Festival in 2011.

Without getting into detail, the Times story reports that Westfeldt still had to fight to get Friends with Kids off the ground. Hamm, for his part, seems to blame the Hollywood glass ceiling for demanding his girlfriend work so hard. 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, Hamm told the Times. There seems to be this expectation of: 'Hold on, lady. You just stay in your place. Don't try to reach for too much.'

Westfeldt was far more circumspect about her impressions of a woman's place in the movie business: We're making progress, slow and steady in this world.

The success of Bridesmaids has pioneered some latitude in the female-driven comedy genre, and Westfeldt seems to have taken advantage of newfound permission for women to be given dialogue that until recently might have been dismissed as crass or unladylike. But it's the male lead in Friends with Kids who delivers the unprintable -- and soon to be infamous -- closing line.

Friends with Kids opens Friday in limited U.S. release.

Watch the trailer here: