Sidewalks of New York (2001 film)

Sidewalks of New York is a 2001 American comedydrama film written and directed by Edward Burns, who also stars in the film. The plot follows eight cycles in the lives of six Manhattan residents whose interconnections form a circle that places each of them less than the proverbial six degrees of separation from the others.

The circle begins with Tommy Reilly, a onetime wannabe writer who became the producer of a weekly television entertainment news show by design rather than choice, and has stayed with it for the money rather than any professional satisfaction. Dumped by his livein girlfriend without warning, he temporarily moves in with colleague Carpo, an aging Lothario ready to offer unlimited and useless romantic advice.At a video store Tommy meets grammar school teacher Maria Tedesko. The two flirt, meet for coffee, and begin to date. Maria, recently divorced, finds it difficult to commit to a new relationship and stops taking Tommys calls. When she discovers shes pregnant, she attempts to reconnect with him, but at the last moment opts to lie and tell him shes leaving town and chooses to raise the child on her own. ........

Source: Wikipedia