Tommy (Edward Burns), a producer for a celebrity news television show, has just been dumped by his girlfriend, who realizes they are not on the same page about having children. He moves in with Carpo (Dennis Farina), a veteran Don Juan who has seduced over 500 women and is eager to pass on his sexual advice to Tommy.

At a Manhattan video store, Tommy meets Maria (Rosario Dawson), a grammar school teacher who hasn't been dating since divorcing her husband Benjamin (David Krumholtz), a doorman and aspiring songwriter. They spend an unusual evening together but she's uneasy about going further in the relationship.

Meanwhile, her ex who still keeps barging in on her unannounced, has developed a crush on Ashley (Brittany Murphy), a 19-year-old from Iowa who works as a waitress. She's been having an affair with Griffin (Stanley Tucci), a middle-aged dentist who's cheating on his trophy wife Annie (Heather Graham). He prides himself on his "European" attitudes toward love and marriage. Annie, on the other hand, is an idealist who believes in true love and the necessity of fidelity in a marital relationship. However, once she intuits that her husband is cheating on her, Annie takes an interest in Tommy, who is a real estate client of hers looking for an apartment.

In his fourth feature film, (The Brothers McMullen, She's the One, Looking Back), writer, producer, and director Edward Burns captures the uneasiness of urban men and women in romantic relationships. Although sex remains the omnipresent urge, the supreme itch and the compelling force, these New Yorkers remain wary of each other even when they're turned on by each other.

In the marriages depicted on the screen, trust is broken into pieces as husbands and wives are either adulterers or cheated upon by their mates. At one point, Tommy says: "If we had answers, all of us would be in these great, solid, happy relationship. But so few of us are. We're searching for that thing and we have so much trouble finding it. But who knows, maybe that's part of the fun." Right, except in this search, fun seems quite desperate.

The DVD includes an audio commentary from Edward Burns, the screenwriter, director, and star.