Ep 23. Bart's Friend Falls in Love

In The Simpsons season 3, episode 23, "Bart's Friend Falls in Love," Bart Simpson's best friend Milhouse Van Houten falls head over heels for the new girl in school, Samantha. After seeing her perform a sultry dance at the school talent show, Milhouse becomes infatuated with her and starts to do everything he can to impress her.

Bart tries to help his friend win her over, but soon realizes that Samantha is not interested in Milhouse and is only using him to get closer to his wealthy father. Meanwhile, Homer and Marge are dealing with their own marital issues, as their attempts to spice up their love life lead to more frustration than passion.

As Milhouse becomes more desperate to win Samantha's affections, he starts to neglect his friendship with Bart and becomes increasingly isolated from the rest of the school. When Samantha's true motives are finally revealed, Milhouse must confront the harsh reality of his unrequited love and learn to move on.

The episode explores themes of adolescent romance, social hierarchy, and the challenges of maintaining relationships amidst outside pressures. Featuring the iconic humor and witty writing that have made The Simpsons a cultural phenomenon, "Bart's Friend Falls in Love" is a standout episode that showcases the show's enduring relevance and enduring appeal.