The Wandering Juvie

"The Wandering Juvie" is the sixteenth episode of "The Simpsons"' fifteenth season. It originally aired on the Fox network in the United States on March 28, 2004. It guest-starred Sarah Michelle Gellar as Gina Vendetti. It also guest-starred Charles Napier and Jane Kaczmarek. Bart gets sent to juvenile hall after registering for gifts at a department store and having a fraudulent wedding to obtain gifts. This episode sees the first appearance of Gina Vendetti, who later appears in "Moonshine River".
Plot.
When the Simpson family is at the Costington's department store, Bart uses the wedding gift registry as a prank to register himself and his bride, "Lotta Cooties", for wedding presents. Bart invites many people to his so-called "wedding" and plans to take all the unused gifts back for store credit, but he is stopped by Chief Wiggum, who arrests Bart and rejects his bribe of the wedding presents. Bart is sentenced to six months of juvenile detention by Judge Constance Harm.
At the detention center, Bart is afraid he will be buried alive in the sandpit or photographed being punched while going down a slide. He soon notices that the girls' Juvie is on the other side of a chain-link fence. Bart attempts to schmooze with these girls, only to have them attack and immobilize him. One of the girls, Gina Vendetti, uses a knife to destroy Bart's uniform, threatening to castrate him next time he comes near their fence. Bart's problems continue when two weeks before his release he is partnered with Gina for the dance by the warden. When they are dancing, Gina escapes with Bart using a rope, finding themselves on a window ledge. Due to the fact that they are handcuffed together, Gina is forced to bring a reluctant Bart along before the window can be closed, though he only comes after she kisses him. Slowly, they gain each other's trust.
On the lam, the duo look for a blacksmith who can remove their cuffs. They are freed, but after it happens, Gina is alone and forlorn. She starts crying and admits to Bart that she has no family. When he sympathises with her, she angrily tackles him until the police come and arrest them (and a bear that Cletus correctly predicted would attack Wiggum). Feeling terrible for causing Bart's sentence to be extended, Gina confesses that she was behind the escape, clearing Bart of further charges. In the end, the Simpsons and the warden step in to help Gina feel better for being without family, offering a Mexican food feast in her cell.