Damon goes to a sporting goods store to buy some athletic shoes, but ends up buying a lot of camping equipment he doesn't want to impress Monique, the pretty sales clerk, and accepting a date to go camping with her and her friends. Billy has joined Big Brothers of Chicago; he brings his little brother Elvin to headquarters to sell candy for a school fundraiser.
Damon, in full African garb, visits an antique shop in an attempt to bust the owner for selling illegal ivory. Woody Woodson, the famous actor, is hanging out at the precinct doing some research for his new TV series. Everyone, especially the Captain, is star-struck with the exception of Damon, who finds Woody's presence an annoying distraction. Damon's upset when the Captain informs him that Woody will be following him around for a few days.
Bernard's depressed, he tells Damon, because he's a failure at everything: he's single, a security guard and sleeps on his brother's couch. Bernard says he should take the police exam, but Damon reminds him he's failed five times. Furthermore, every time Damon tries to help Bernard, Bernard wants to do it his way.
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.