Damon and his partner Stacy, two cops, go undercover as a pimp and his hooker to nail Runuti, the owner of an escort service; Damon's brother Bernard is having marital problems, so he's sleeping on Damon's couch.

Damon goes undercover in a jail and tricks a couple of bank robbers into revealing where they've hidden the stolen money. Back at the squad room, the Captain announces it's time for the annual physical; no one's getting out of it, and that means Damon. Damon goes to get his physical, but when it's time for the prostate exam, he's gone.

Damon goes undercover on a drug money laundering case and encounters Ally, a sexy Jamaican girl whose accent makes him fall in love; there's instant chemistry, and Damon adopts his own Jamaican accent just to make it interesting.

After Damon makes a successful bust at the airport, Tracy Warren, a Chicago Sun Times reporter, tries to interview him, but Damon keeps hitting on her. Damon's neighbors down the hall are moving, and he realizes that a perfect way to get rid of Bernard is to have him move into their apartment.

Damon's doing everything he can think of to get Tracy to go out with him. Bernard, feeling protective of his new roommate, tells Damon to back off; Tracy's coming off a bad divorce and she needs her space.