The Simpsons

Season 20 Episode 17:

The Good, the Sad and the Drugly

Bart falls in love with a charitable girl named Jenny, prompting Bart to behave in order to date her. Meanwhile, Lisa becomes depressed when she writes a report on Springfield's future.
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About The Simpsons:

Set in Springfield, the average American town, the show focuses on the antics and everyday adventures of the Simpson family; Homer, Marge, Bart, Lisa and Maggie, as well as a virtual cast of thousands. Since the beginning, the series has been a pop culture icon, attracting hundreds of celebrities to guest star. The show has also made name for itself in its fearless satirical take on politics, media and American life in general.