Tommy (EDWARD BURNS) is a television producer who's getting back into the world of dating after breaking up with his long-time girlfriend and thus takes advice - with a grain of salt -- from his show's cocksure host, Carpo (DENNIS FARINA), who claims to have bedded hundreds of women.
When Tommy meets Maria (ROSARIO DAWSON) at the local video store, he's instantly smitten. She, on the other hand, is still recovering from a divorce stemming from a teenage marriage, and a friend of hers, Shari (AIDA TURTURRO), isn't so sure she should have given her number to Tommy. Meanwhile, Maria's ex-husband and local uniformed doorman, Benjamin (DAVID KRUMHOLTZ), is still reeling from the divorce, but has found himself attracted to Ashley (BRITTANY MURPHY), a young waitress in Greenwich Village.
Although she likes Benjamin, she's the young paramour to Griffin (STANLEY TUCCI), a self-centered dentist who treats her like dirt while cheating on his real estate agent wife, Annie (HEATHER GRAHAM), who's growing increasingly suspicious of Griffin's behavior. As she then shows Tommy around the city as he looks for a new place to live and she wonders if she should start seeing him, the various characters' personal circles intersect as they all try to sort out their romantic relationships.