NEW YORK, N.Y. - "First of all, I'm an Aquarius."
Jennifer Westfeldt is only half-joking in explaining how she came to be a combatant of convention. In the past 10 years, she has written and starred in three films, each of which takes the anxiety of a particular passage of adulthood — dating, marrying, parenting — and comically, candidly pursues them from an untraditional perspective.
In 2002's "Kissing Jessica Stein," the film that catapulted Westfeldt to chic indie status, her character tires of the kind of men who describe themselves as "self-defecating" and gives lesbianism a shot.
Five years later, in "Ira & Abby," she played a twice-divorced woman who abandons the considered courtship that led only to heartbreak, and gets hitched on a hunch.
And now, after another five years, Westfeldt is back with "Friends With Kids," which opens Friday in limited release, and she's directing for the first time, too.
Westfeldt plays Julie, a 30-something New Yorker who has a child with a platonic friend, Jason (Adam Scott), in hopes of maintaining a romantic single life and foregoing the trappings of married parenthood.
"If someone says something's impossible, I'm always like, 'Really?'" says Westfeldt over tea at an Upper West Side restaurant. "I don't just follow or believe things that are dictated. I'm always wondering why it has to be that way."
Westfeldt, 42, doesn't look like a rebel. She's a smiley, earnest, down-to-earth, fashionable Upper-Westsider, who chats cheerfully while brushing back her long blonde hair.
"She's an open book," says Jon Hamm, her boyfriend of 14 years and a co-star of "Friends With Kids." ''There's not a lot of subterfuge or deflection in her, probably to her detriment. Sometimes the press can be a nasty beast, no offence. She is the most open-hearted, sweetest most loving person that I know. And I think that's pretty obvious in the work that she does."
That work includes stints on Broadway and numerous TV series, but her most personal work are her three penned films, all of which bely an instinct to reexamine society's assumptions.
"Friends With Kids" may sound like a facile premise, but the title has a double meaning. As much as the film is about a pair of friends having a baby, it's about the experience of seeing your close friends marry, move to the suburbs (or, in the film, Brooklyn) and lose their old identities behind a BabyBjorn wall.
Julie and Jason's circle of friends have all crossed the child Rubicon, with varying results. Maya Rudolph and Chris O'Dowd play a sleep-deprived couple drowning in diapers but making it through, while Kristen Wiig and Hamm are paired in a relationship becoming undone by the stress of parenting.
Much of the film, shot on a small budget over four weeks last year in the midst of one of New York's snowiest winters, is centred on a trio of dinner scenes. With cinematographer Will Rexer, Westfeldt studied the camera movements of large dinner scenes in films like "Hannah and Her Sisters" and "The Big Chill."
"It really was the ensemble dynamic that I was most interested in," says Westfeldt. "The original kernel was just being out of sync with my peer group."
Scott and his wife, producer Naomi Sablan, are longtime friends of Hamm and Westfeldt. With two kids of their own, they were very much a part of those peers.
"My first reaction when I read the script was that I was very moved by it, but at the same time, I was just kind of like, 'Oh s---. I'm sorry, you guys,'" says Scott. "We were exactly those friends who disappeared when we were at home with a colic-y baby."
Hamm and Westfeldt don't have children, themselves. They split time between New York and Los Angeles, where they have a house and a beloved shepherd mix rescue.
"Jon says we live in L.A. I say we're entirely bicoastal," says Westfeldt, unready to divorce herself from a Manhattan identity. She grew up in Guilford, Conn., the younger of two daughters to divorced parents. (Full disclosure: Jennifer's sister, Amy Westfeldt, is a reporter for The Associated Press.)
The relatively recent fame that "Mad Men" has brought Hamm has made their relationship more public than either Westfeldt or Hamm would like. Westfeldt stresses the importance of keeping a separate, private life outside of "the swirl," and shrugs at the prying: "What are you going to do?"
Westfeldt, who fell for acting in the fourth grade playing Alice in "Alice in Wonderland," had renegade leanings from the start. Laughing at her "checkered past," she recalls being kicked out of a theatre camp after stepping out for pizza with a boyfriend.
"I guess I have been a rule breaker," she says. "It's funny because in some ways, I'm so traditional," says Westfeldt. "I'm such a romantic. I'm a serial monogamist."
But it was the same spirit of ingenuity that birthed Westfeldt's writing career. After bouncing around sitcoms and various TV pilots, Westfeldt attended a workshop that led to an unexpected writing collaboration with actress Heather Juergensen. Their play, "Lipschtick: The Story of Two Women Seeking the Perfect Shade," ran for just three nights in a small New York theatre but attracted Hollywood's attention. They turned it into "Kissing Jessica Stein."
Westfeldt may have found a minor generational sensation again with "Friends With Kids," a film easy for those in their 30s and 40s to relate to, and one New York Magazine has hailed as "the best breeder movie in years."
Though the film — like her previous ones — inevitably edges toward a more conventional ending, Westfeldt, predictably, isn't so sure of such a tidy future for any of her characters.
"There's never an end to the ways in which arrangements and relationships get complicated and the two sides tested," she says. "Life is complicated, right? And it continues to be."
Jake Coyle can be reached at http://twitter.com/jake_coyle