Waylon Smithers and Mr. Burns go skydiving together, but Burns blacks out and slips through his parachute, so Smithers jumped after him, managing to catch Burns during freefall and rescue him. When they landed on the ground, Smithers chose to proclaim his love to Burns, but he is completely ignored. Having become miserable, Smithers chooses to supervise the work from the Plant's employees: Homer, Carl and Lenny. They realized what was going on, so Homer planned to find a new companion for Smithers so he would not be crestfallen while working.
Homer invited all of the gay men from a dating app, Grinder, to a party where Smithers could choose his new love, but he got irritated and chose to just take a drink and leave. At this moment, he meets Julio, and they fall in love with each other. Smithers quits his job at the power plant and chooses to move to Julio's homeland: Cuba.
With Smithers out, Burns tried to find a new replacement for him, but everyone failed miserably. Next to that, matters weren't going well in Cuba either, as Julio discovers that Smithers hasn't gotten over Burns yet. They break up and Smithers travels back to Springfield, where he and Burns reconcile at a pleasant dinner.
On a secondary plot, the Springfield Elementary School was making a Casablanca play. As Lisa manages to get the role of Ilsa, Milhouse auditions to the role of Rick so he and Lisa could be the play's main couple. However, a new kid named Jack gets the main role. As only him and Milhouse auditioned for that character, Bart plans to withdraw Jack from the play by getting Dolph, Jimbo and Kearney to beat him, but their plan backfires as Jack defeated them. However, Principal Skinner observes Jack beating the bullies and withdraws him from the play, giving the supporting role to Milhouse.
Lisa is crestfallen, fearing that Milhouse's lack of talent could ruin the play, but Marge convinced her to support Milhouse so he could do better. At the play, Milhouse gets his lines perfectly, surprising everyone. At the end of the play, however, it is revealed that Jack was playing Milhouse dressed as Rick, and he and Lisa go out for a root beer float together.