Smithers helps Moe turn his tavern into a popular gay bar, but later on Smithers gets offended at Moe for pretending to be gay. Meanwhile, Skinner develops a crush for the new music teacher—Ms. Calliope Juniper—so he talks Bart into going on a date with Ms. Juniper's daughter, Melody, with him and Calliope being chaperones.
Feeling down after finding out Mr. Burns didn't put him in his will, Smithers tries to cheer himself up by going to a gay nightclub, but feels even worse when he and several other men (such as Mr. Largo) are rejected for not being in great shape and fashionable. Smithers soon convinces Moe to change his bar into one for more average gay men like himself. Moe initially declines, but after Barney walks out of the bathroom with Moe's Grandmother's Wedding Urinal (Barney thinks the urinal is his buddy), Moe ultimately agrees to change his bar, learning that he can increase profits by allowing this idea. Moe pretends to be gay in order to invite new consumers. As a result, he wins the trust of the gay community to the point they want him to run for city council. This causes problems for Smithers, who threatens to 'out' Moe as a heterosexual. Given this threat, Moe wonders if he should come clean or allow Smithers to go ahead with the outing. After revealing the truth, the crowd becomes angry and leaves. Moe, feeling like he has nothing to lose, kisses Smithers, stating, "Like Frisbee golf, I'm glad I tried it once."
Meanwhile, Principal Skinner falls in love with Ms. Juniper, who replaces music teacher Mr. Largo. Skinner tries in many ways to make her fall for him, but hopeless as he is with women, he asks Bart for help in winning the new music teacher's heart by having Bart date Juniper's daughter, Melody. After Bart breaks up with Melody, Juniper and Melody move out of town. Before taking off, Miss Juniper asks if Skinner wants to come with them. Willie becomes both the Principal and Groundskeeper on Skinner's leave of absence. Skinner returns to Springfield three months later as revealed by Bart.