Medavoy decides to go on a diet and has a hard time getting started on it. Meanwhile, Sipowicz has problems with his work, his baby son's illness and Sylvia deciding to return to work at the D.A.'s office. Simone proposes marriage to Russell, but she is hesitant to give him an answer. Martinez has eyes for Gina Colon the new administrative aide for the anti-crime unit since Lesniak has been transferred from the squad to another precinct, thus leaving the 15th for good. But none of the men are turned on by Donna's latest replacement, a frumpy lady named Gerri Turner as the PAA for the squad but she has a strong interest in Sipowicz. A body in a trunk of a car is inadvertently moved from the nearby 13th precinct into the 15th's jurisdiction. Elsewhere, Simone inherits an apartment building from a recently deceased woman and the woman's son, Henry, is upset at the situation.

Medavoy starts a bet with Sipowicz to see who can lose the most weight in a single month. Afterwards, Sipowicz and Simone help out Detective Stuart Morrissey on his investigation in the case of a missing baby. Meanwhile, Martinez campaigns to become the elected delegate for the squad and his opponent, Detective Vince Gotelli, is determined to win the seat himself. Also, Simone makes a deal with Henry to let him share ownership of the building.

An ex-con that Sipowicz put away a year ago approaches him and tells him about a prisoner who's been serving time for a crime he didn't commit and he and Simone decide to reopen the case. Meanwhile, Martinez wins the election by just three votes, much to Gotelli's chagrin. Simone comes across Detective Nick Savino who helps him with the investigation of the murder in his building and Savino suspects Henry has something to do with it. Fancy gets a cavity filling which makes him more edgy than usual and Medavoy loses one pound more than Sipowicz. Also, Russell still has not come to any conclusion about her relationship with Simone.

A foreign prince and princess are assaulted - the princess goes into a coma. Sipowicz and Simone investigate, with Mike Roberts help, who provides them with some information about Prince Foresmann's contacts over some stolen artwork. Meanwhile, Martinez's first delegate situation gets a resolution that keeps Officer Ortiz out of trouble with the department. This doesn't work out as planned when two women claiming to be his wife are arrested in a scuffle. Russell begins a new undercover job that involves her getting into a relationship with alleged drug dealer, Jimmy Liery, that might require her to start drinking again. Elsewhere, Geri continues to try to win Sipowicz's affections and Medavoy for once feels good about himself after his diet. Also, Martinez asks the anti-crime PAA, Gina Colon, out on a date.

Simone and Sipowicz look into the death of a limo driver and try to find his last clients which included a gay businessman trying to cover up his secret cruising lifestyle. At the same time, Sipowicz finally lodges a complaint against Geri that gets her moved up to the crime lab area, while Gina is transferred down to the squad floor. Meanwhile, a new detective, Jill Kirkendall, joins the squad. Her first case involves investigating a man whose life is being threatened and this leads Kirkendall to suspect that the man's assailant's girlfriend has a stolen infant. Simone gets the approval from Detective Savino to question Henry about the apartment shooting and finally gets the real story. Also, Russell can't figure out how to talk to Simone about her current assignment.

Simone, Sipowicz, Medavoy and Martinez together conduct an investigation into the death of a worker at a construction site, where more than a building is being framed and try to sort out a feud between two different unions. Meanwhile, Geri reports to Sipowicz about finding a friend of hers who has hung himself and Fancy suggests that Russell and Kirkendall conduct the investigation, which reveals the man died from kinky sex... with Geri. But the dangerously disturbed, sex-obsessed Geri will not speak to anyone about the case except for Sipowicz whom she has an obsessive crush on. Martinez stays close to Gina while she is recovering and preparing to get her stitches from her horribly scared face removed and offers him to let her stay the night with him.