S3E22: The Otto Show

In "The Simpsons" Season 3, Episode 22, titled "Bart's Friend Falls in Love," we see Milhouse fall head over heels for a new girl named Samantha Stanky. Bart, feeling left out, tries to sabotage their relationship by tipping off Samantha's strict father. The plan works a bit too well, and Samantha is sent to a convent school, leaving Milhouse heartbroken. Bart and Milhouse's friendship takes a hit due to Bart's meddling, but they eventually reconcile after a heart-to-heart talk at the Springfield Observatory. Meanwhile, Homer is obsessed with a subliminal weight loss tape but accidentally gets one for vocabulary building instead, leading to some hilariously verbose moments. By the end of the episode, Bart and Milhouse restore their friendship. Homer’s unintended vocabulary enhancement leaves him speaking with an uncharacteristic eloquence, which baffles Marge and adds a comedic twist to the episode's close.