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:

* ConvenientlyTimedDistraction: When Chloe tries to get Mayor Quimby to answer some questions about his multiple paternity suits filed against him, she gets distracted when she sees Marge again allowing Mayor Quimby to run back into his office to avoid answering her questions.
** When Tom Brokaw and Dan Rather are picking on Kent Brockman by teasingly dangling his microphone out of his reach, they get distracted when Chloe greets them giving Kent the opportunity to take back his microphone.
* [[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 microphone out of his reach.