A documentary film crew follows the lives of six New Yorkers as their lives unexpectedly intersect. or at least that's what writer, director, and actor Edward Burns would like you to believe in this comedy-drama that looks at the rocky road of relationships in the Big Apple. After sharing the stories of their earliest sexual experiences with an interviewer, six people are trailed by a cameraman through the course of an average day. Tommy (Edward Burns) is a successful television producer (and unsuccessful novelist) who becomes quickly infatuated when he meets Maria (Rosario Dawson) in a video store. Maria is a teacher at an upscale private school who has just gotten out of a bad marriage with Ben (David Krumholtz), a struggling musician with a day job as a doorman. Ben, on the other hand, finds himself attracted to Ashley (Brittany Murphy) when she waits on his table at a coffee shop. Ashley, as it happens, is involved in an affair with Griffin (Stanley Tucci), a dentist who is chronically unfaithful to his wife Annie (Heather Graham). Annie, a real estate agent, also happens to be friends with Tommy, one of her customers, bringing the circle to a close. Shot in only 16 days, Sidewalks of New York marked a return to (relatively) low-budget filmmaking for Edward Burns, who directed two less-than-successful major studio projects following his breakthrough with the independent feature The Brothers McMullen.