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Jennifer Aniston plays Olivia, the youngest and least established of the four longtime friends. Olivia, in fact, is in a wicked funk cleaning houses for a living and phone-stalking a married man. Her companions are far better off, at least financially. Christine (Catherine Keener) and her screenwriting partner and husband, David (Jason Isaacs), are adding a second story to their large home. Franny (Joan Cusack) and husband Matt (Greg Germann) have donated $2 million to their daughter's school, for lack of a better idea. And Jane (Frances McDormand) is a successful fashion designer with an adoring husband (Simon McBurney). At a birthday dinner for Jane, Olivia is the only single woman and the only one without a career or money. Sure, crocodile tears, but remember: This is Los Angeles no matter what your subculture, it's hard when your friends have amassed status symbols beyond your grasp.
As the film plays out, though, cracks in the relationships emerge and are discussed among the others. That's one of the maneuvers Friends With Money has nailed: talking about others as a means of distraction from oneself. Every time two people in the film near conflict, they veer away by discussing (and evaluating and analyzing) someone else. That's not cynical so much as honest: We all use whatever tools we have to avoid problems, including the lives of our friends. And these characters are friends; when things turn to shit for Christine and David, Jane and Aaron step up. It's just that what they have to offer is limited by the things about themselves that they can't or won't acknowledge.
Aniston has a thankless job as Olivia. She does fine, but it isn't easy to bother about a character who can scarcely be bothered herself. Keener and McDormand are given far more meat to work with, and they tear into it and chew. Cusack is her usual winsome self, calm and motherly, almost goofily content (or absent).
Maybe Holofcener's is a Los Angeles brand of feminism, where empowerment never strays too far from film or money. Maybe this is what happens to women who think that, once they've acquired the requisite signifiers, everything else will take care of itself. Maybe their lives become superficial, or maybe they always were.