Ep 16. Bart the Lover

When Bart's class is assigned to write a letter to someone in the public eye, he decides to write to Ms. Krabappel, his teacher who he thinks is lonely and desperate for love. Under the guise of a man named Woodrow, Bart writes a romantic letter to her, which Ms. Krabappel finds and is thrilled by. She begins a secret correspondence with "Woodrow", not knowing it is actually Bart.

Bart then continues to send letters to Ms. Krabappel as "Woodrow", creating an entire persona for the man. He even enlists his family's help in creating a voice for Woodrow when Ms. Krabappel calls and "he" answers the phone. As Bart continues to weave this web of deceit, he begins to feel guilty about the pain he is causing Ms. Krabappel, but doesn't know how to come clean.

However, everything comes to a head when Ms. Krabappel decides to throw caution to the wind and meet "Woodrow" in person. Bart desperately tries to figure out how to get out of meeting her, but ultimately must face the music. The aftermath of their meeting leads to some unexpected twists and turns, including Bart learning some valuable lessons about the importance of honesty and communication.

Overall, "Bart the Lover" is a hilarious and heartwarming episode of The Simpsons that showcases the show's ability to balance humor and poignant moments. The episode explores themes of loneliness, love, and the consequences of deceit, making it a standout episode in the show's storied history.