When Smithers is devastated by Burns' lack of affection towards him, Homer makes it his mission to find him a boyfriend. Meanwhile, after Bart orchestrates the removal of the lead in the school's stage production of "Casablanca," Milhouse serves as a terrible understudy, which frustrates his co-star, Lisa.
After getting into an argument, Marge takes Lisa on a touristy trip to Capital City, where, after attending a musical, they meet the show's star, Andrew Rannells (guest-voicing as himself), who reminds Lisa how lucky she is to have such a great mom. Meanwhile, Bart is frustrated that everyone expects his pranks, so he teams up with Maggie to trick people.
Homer recalls a tense family vacation to the Grand Canyon with the Flanders family. At first, the Flanders' perfection puts the families at odds, but when they get stranded and Ned and Bart go for help, the families finally bond.
After promising Marge the trip of a lifetime, frugality gets the better of Homer when he makes a deal with a travel agent to be a courier of a top-secret briefcase in exchange for a discounted family vacation to Paris.
After butchering a speech in front of all of his friends at work, Homer turns to improv comedy to gain back his confidence in his public speaking skills. Meanwhile, Marge decides to rebuild Bart's lackluster treehouse, but tensions rise when Bart questions her building skills. Also, in the episode's last three minutes, Homer appears live for the first time on television (both for East and West Coast broadcasts) to answer fan questions.
When Marge gets arrested for letting Bart go to the park unsupervised, she serves time only to realize that prison is a welcome break from the demands of her life as a mom and wife. In her absence, Homer struggles to manage all of the parenting responsibilities that Marge usually handles.
When Springfield is burned to the ground, the Simpsons beg Mr. Burns to fund its rebuilding. Burns agrees – with one condition: he gets to put on a variety show at the Springfield Bowl.
Mr. Burns hires the Simpsons to play his live-in virtual reality family, but excludes Homer so that he may play dad. Now alone, Homer finds a new best friend in girl-next-door Julia, who eats, drinks and thinks like him.
After Homer catches Bart rooting for Springfield's football rival, the Boston Americans, he plans a family "hate-cation" trip to Boston in an attempt to show Bart that Boston is a terrible city.
In the midst of a major drought, Mr. Burns introduces a Hunger Games-style contest in which Springfield's children fight each other for a day in Burns' personal reservoir. Meanwhile, Lisa's imaginary best friend, Rachel, is jealous of Lisa's real best friends and starts killing them. Moe tells Bart that the barflies are actually covert agents and that he wants Bart join their team in Homer's place.
Lisa and Bart investigate Krusty's suspicious new "Krustaceans" candy. Meanwhile, Homer wants a promotion at the nuclear plant and asks Marge to help him dress the part, and news anchor Kent Brockman struggles to find his feet in the changing media world.
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