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.

Simone and Sipowicz investigate the murder of a woman whose body was found naked in the trunk of a car in a junk yard which leads them to a pervert with a penchant for lookalike porn actresses. Meanwhile, Martinez and Medavoy investigate a man who was found dead with a severe blow to his head from a typewriter. Simone hires Henry to take care of a painting job in the tenement building, where Henry comes in complaining about a difficult tenant. The emotionally and physically scarred Gina returns to work (with a large vertical scar across her left face), and Russell is working through her issues with her family problems by meeting a counselor.

Youthful detective Danny Sorenson joins the squad and, during a multiple homicide investigation, discovers that his new colleagues have yet to recover from Simone's death.