Marge bumps into an old high-school acquaintance (voiced by Kim Cattrall from ''SexAndTheCity'') who is now a successful news reporter. While Marge becomes jealous of her friend's success and wonders what may have been had she not stayed with Homer, Lisa becomes inspired by this new, strong woman.

!! Tropes:

* [[SelfMadeMan Self-Made Woman]]: Chloe Talbot.
* ShoutOut: Having "no time to be picky", Lisa was desperately praying to {{Buddha}}, {{Jesus}} and [[SpongeBobSquarePants SpongeBob]].
* ThisJustIn: Kent Brockman was upset at the reporters who were teasingly dangling his microfone out of his reach.