Sipowicz has a cavity and decides to have it taken care of by his son's dentist. At the dental office, Sipowitz finds himself unsuccessfully trying to prevent the suicidal Dr. Fleishman from jumping off a 28th floor ledge. Meanwhile, Medavoy and Martinez work on a strangulation murder case that appears to be the work of a cross-dresser. LaSalle's first case for the squad involves a woman who was raped and she, Kelly, Sipowicz try to catch the most probable suspect. Janice joins the undercover squad and is partnered with the hot-tempered Roy Larson to assist with LaSalle's case, while Sipowicz suspects that Larson's short temper and odd behavior points to a drug problem. Also, Lois Snyder (the prostitute who set Sipowicz to be shot in the premiere episode) returns to try to apologize to him about the incident and also wants to renew their romance. But Sipowicz turns her down and goes back to start whatever relationship she has with D.A. Sylvia Costas.

Lt. Fancy insists to a reluctant Larson that he take a drug test and when it comes back positive of methamphetamine use, he is fired. One of Detective Mike Roberts' informants/girlfriends comes to the precinct and causes trouble for him, especially when she later turns up dead, and Roberts becomes a suspect. Although Roberts ends up being cleared, his reputation is ruined and he decides to quit the police force. Meanwhile, Sylvia has trouble getting through to Sipowicz to give their relationship another try. Also, Laura appeals to Kelly to help her re-examine a case she is prosecuting of the alleged murder of an abusive man by his wife, in which Martinez and Medavoy investigate one witness and discover some conflicting facts in the case.