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.

Sipowicz is taken hostage in an interrogation room by a suspect in the murder of a pot dealer and two of her friends; a suburban mom found with drugs in her purse appears to be covering for her son.