First Aired: May 4, 2008
Plot: While waiting for Brian at the vet's office, Chris meets a young intern named Anna (Amanda Bynes) and develops a crush on her. Meanwhile, Peter becomes very attached to a parrot he sees at the vet and decides to steal it for himself. He carries his parrot wherever he goes, so Peter's friends compare him to a pirate and suggest he dress up like one. He does, and recruits three other pirates to begin terrorizing the town under the name "Long John Peter". Peter and his men loot British man Shelley Boothbishop's car full of sugar cane, tobacco, and spices in a drawn-out high-speed car chase that mimics a naval battle, filled with cannonade and sword fighting on each side. Peter's parrot is gravely injured in the attack and dies a reportedly humiliating death at the vet's office, though Peter quickly gets over it in favor of a pipe organ (which, too, soon meets it's demise at Peter's hands).
Whilst at the vet's office, Chris meets up with Anna again and musters up the courage to ask her out. The relationship goes very smoothly until Peter berates Chris for treating her like a human being. Taking Peter's advice on male superiority, Chris puts Anna down on their next date so he can make progress with her. Understandably Anna breaks up with him instead. Chris laments his experience to Lois, who forces Peter to make it up to his son. Peter's decides to hook Chris up with other girls, though his efforts consistently fail.
After Peter's ideas are exhausted, Lois comforts Chris and says that though his father's intentions are good, the only person he should turn to in this situation is himself. Chris returns to the vet to see Anna (he intentionally broke Brian's nose with a chair as an excuse to go back to the vet), apologizes to her and kisses her. Anna forgives Chris and the two renew their relationship. The episode ends with a severely disfigured Brian collapsing on the floor and pleading for help, only for Stewie to come out of nowhere and kick him in the gut.