Nick and Naomi's affair-that-probably won't happen is yoked to many parallel plots, all having to do with characters that are struggling to be productive and happy despite feelings of ennui that they can't quite explain. Naomi, Nick and Alyssa all suffer from this affliction, as does Alyssa's sister Gwen (Mary-Louise Parker, stealing the movie, as she tends to do), who hired Nick to go through the collected papers and memorabilia of their recently deceased pack-rat of a father.
Naomi has a sort-of-crush on Buddy (Jason Schwartzman, who's turned literate unctuousness into an aesthetic), a music producer who knew her when she was a girl (he was older, though not Nick-older). Buddy offers to hang out with Naomi as a favor to his mom, but it's immediately clear that he has other designs on her. He initially fails to disclose the gender of the "friend" that he tells his wife Jess (Analeigh Tipton) he's going to meet for a beer, then makes a too-ostentatious show of transparency when he tells her that the friend is female and her name is Naomi. Buddy shares every major character's chronic inability to be happy with where they are and who they're with. So it's not a giant shock when he starts fixating on Naomi, even after assuring her he's not interested in her in that way.
Perry and his regular cinematographer, Sean Price Williams, shoot this story on Super 16mm film, which gives the entire movie a creamy, grainy softness characteristic of features from the pre-Internet era. The neighborhood, the interiors and the characters' faces all have a subtle glow. You get to know the neighborhood so well that you can identify Naomi's house, just one Brooklyn row house among many, when Nick passes it; that's how you know Nick is doomed to go back and try to talk his way upstairs. Perry is perhaps too oblique or evasive for his own good when plotting his characters' stories and elucidating their problems (even for a film that announces itself as a "nothing happens" movie, there's a lot of nothing happening here), and there are too many scenes where characters trade monologues, some of which sound like philosophical position papers. But his direction is unerringly precise, often framing one or two characters as a scene begins, then slowly zooming in or out until the point has been made, avoiding cuts unless absolutely necessary. Visually, the movie seems to be slowly pushing a needle into the lives that it scrutinizes, as if to draw a blood sample and learn what ails the characters.
This is the kind of movie that compels viewers to disclose what sorts of problems they consider important. I'm at a point in my life where, for entirely subjective, personal reasons, I couldn't really relate to any of the characters—except maybe Gwen, who has zero patience for everyone's b.s. even as she dishes out heaping plates of her own, and who eventually snaps and gives Nick the verbal whipping he's been all but begging for. But your mileage may vary, as they say. Naomi tells you up front what kind of movie you're about to see, and she's not wrong.
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