Smithers almost declares his love for
Mr. Burns after he saves Burns' life in a skydiving accident, but Burns reaffirms his indifference and ingratitude for him. Angry and heartbroken, Smithers treats
Homer,
Lenny and Carl harshly, so they decide to find Smithers a boyfriend so he will be better-tempered. They invite potential partners to meet Smithers at a gay men's singles' party, where a neck massage from Julio snaps Smithers out of his bad mood. The two fall for each other, Smithers gives Homer time off with pay for this and Smithers resigns his job at the power plant. Smithers becomes troubled on a trip to Julio's homeland of
Cuba when Julio's carnival outfit resembles Burns; Julio notices and asks Smithers if he is committed to their relationship, and Smithers admits that he is not. Back in Springfield, Burns' attempts to find a new assistant prove disastrous, and his only option is to rehire Smithers. He meets Smithers with money and other enticements to lure him back, but Smithers states that he is not swayed. Burns then says he has kept a secret bottled up: that Smithers' performance review is "excellent". They hug and reconcile. Meanwhile, Springfield Elementary put on a production of
Casablanca, in which
Lisa gets the lead role of Ilsa.
Milhouse wants the male lead role of Rick because of his love for Lisa, but he is challenged by a new boy, Jack DeForest, who dresses, acts and speaks like
Humphrey Bogart. Milhouse enlists the bullies to beat up Jack, but Jack wins the fight.
Principal Skinner sees this violence and declares that Milhouse will play Rick instead of Jack; Lisa is angered as Milhouse is a terrible actor.
Marge tells Lisa that it is important to encourage people who are not skilled by telling them that they are, using the example of Homer. Milhouse does give a great performance and the production is a success, but in the end, it is revealed that Jack was disguised as Milhouse; he and Lisa leave hand-in-hand. In an
epilogue, Milhouse goes to
Moe's Tavern, where Smithers teaches him that romantic setbacks are part of the search for love, and make the pursuit of it worthwhile even if (clearly referring to himself) the odds are that true love will never be found.
Moe tells the pair that he only searches for gold, not girls, and embarks on a treasure hunt with Jack and
Groundskeeper Willie. ==Production==