The structure of the film consists of several subplots which all revolve around an intertwined cast of characters. The film begins by introducing Richard (John Hawkes), a shoe salesman and recently separated father of two. After being thrown out by his wife Pam (JoNell Kennedy), he gets an apartment of his own to share with his children, Peter (Miles Thompson) and Robby (Brandon Ratcliff). He meets Christine (Miranda July), a senior-cab driver and amateur video artist, while she takes her client to shop for shoes, and the two develop a fledgling romantic relationship. Robby, six years old, and his 14 year old brother, Peter, have a joint online chat which he later depicts in another chat session as "))<>((", an emoticon that means "pooping back and forth".
This piques the interest of the woman at the other end and she suggests a real-life meeting. Two of Richard's neighbors, 15-year-olds Heather (Natasha Slayton) and Rebecca (Najarra Townsend), develop a playful relationship with a much older neighbor Andrew (Brad William Henke). He doesn't say much, but he keeps leaving signs on his window about what he would do to each of them. As a result of this relationship, Heather and Rebecca ask 14-year-old Peter, Robby's older brother, if they can practice oral sex on him, so that he can tell them which of the two does it better; so they do. He says both were exactly the same. The daughter of a neighbor peeks in the window and sees what happens at the time, and quickly leaves.
They later come to the neighbor's house intending to have sex with him, as practice, which shocks him, and he pretends not to be home. Meanwhile, Christine's work is rejected by a contemporary art museum, but then later accepted by the curator, who turns out to be the woman who was instant messaging with the brothers. The plots come together in the end, with Peter developing a friendship with the daughter of a neighbor, having been introduced to the hope chest that she has, Christine and Richard displaying a show of mutual acceptance of their attraction to each other, and, as a final plot device, Robby finding that the noise he'd been awoken to every morning very early was that of an early rising businessman tapping a quarter on a street sign pole. When asked why he's doing it, he stops and turns around, saying "just passing the time", and gives Robby the quarter. When his bus drives away and Robby tries it out himself, the sun heightens with each tap, time literally passing as he does it..