Sidewalks of New York (2001)

Six New Yorkers have an interrelated series of relationships. TV producer Tommy, who's just broken up with his girlfriend, has a short relationship with commitment-phobe Maria, who he meets in a video store, and also hooks up with married real-estate agent Annie, who he meets while apartment hunting. Annie is open to a relationship because her husband, Griffin, is cheating on her, which she slowly comes to realize through talking to her friend/co-worker who's gone through the same thing. Griffin, a 39-year-old dentist, is cheating with 19-year-old waitress Ashley, who he picked up in a park; she realizes she can do better when Ben, a hotel doorman and aspiring musician, tries to pick her up, in a belated attempt to recover from his divorce a year ago from schoolteacher Maria (the same Maria from the video store). Most of these relationships seem driven more by a desperate need to be in a relationship than actual love.