Sidewalks of New York is a comedic drama about the interconnected lives of six New Yorkers. Tommy Reilly (Edward Burns) is a television producer who was recently dumped by his girlfriend. One day he meets a school teacher, Maria Tedesko (Rosario Dawson), and though the two of them connect, she is afraid to make a real commitment to him. One of the reasons that she resists getting together with Tommy is that her ex-husband, Benjamin Bazler (David Krumholtz), is still in love with her. He is also in love with a waitress named Ashley (Brittany Murphy), who is involved with an older married man named Griffin Ritso (Stanley Tucci). Griffin's wife, Annie Mattthews (Heather Graham) soon falls in love with Tommy, creating a strange web of romantic intrigue and deception. Ultimately, each character is forced to examine his or her life and determine whether true love actually exists on the sidewalks of New York.