Director James Gray tells an all too realistic love triangle. There is the good girl who's a friend of family. Then there is the "girl of his dreams." Who the guy ends up with says a lot of about what he thinks of women and even more about himself.
Leonard Kraditor (Joaquin Phoenix, WALK THE LINE) has just gotten out of the hospital. He has some emotional problems. His parents, Reuben (Moni Moshonov, WE OWN THE NIGHT) and Ruth (Isabella Rossellini, BLUE VELVET), introduce him to the daughter of their business partner. Sandra Cohen (Vinessa Shaw, 3:10 TO YUMA) is a kind girl who's a little shy and isn't ashamed to be set up with a guy by her parents. Then Michelle Rausch (Gwyneth Paltrow, SHAKESPEARE IN LOVE) moves into the building. She's a tall, sexy blonde party girl and Leonard is smitten on first sight. She knows it and takes him in like one would a stray dog. Easy attention and loyalty. But in reality she already owns a fickle cat. Ronald Blatt (Elias Koteas, PROPHECY) is the rich married man she's having an affair with.
Leonard likes Sandra, but he really likes Michelle. But he can't let go of either of them no matter what he or they feel. Sandra is the safe bet, while Michelle is the long shot. He's hedging his odds. This description makes him seem like a cad, but he's really just pathetic. The fact that we don't hate him is a testament to Gray and his performers.
Phoenix does give Leonard an immaturity, but also a fragility. As things get more serious with Michelle, the audience relates to his joy. We worry about his fragile emotional status though. Shaw's character seems too good for him from the get go. She gives her desperateness that makes us understand why she'd want to give this emotionally distant "nice guy" a chance. Leonard is nice to her; he's just distant. Sandra wants to heal him.
But what Leonard thinks will fix him is a girl that he doesn't think he could have ever gotten. Cue Michelle. Paltrow gives a great performance as the girl who knows how she makes men feel. The key to how she plays the character is how she makes Michelle a user who doesn't really understand what she's doing. She likes Leonard as an amusement and a friend, because she knows he'll do anything for her. She's the kind of girl who knows a lot of people, but none of them are real friends. Because she needs Leonard, she's just going to pretend that he's just her friend and that he feels the same. In her head she's just being nice.
As events play out, the characters act out of their natures for better or worse. Gray shows guts in doing so. They're all damaged people and they can't all have happy endings. Who we're rooting for and rooting against at the end says a lot about what we think of these characters for better or worse.