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:

* ComicallyMissingThePoint: When Chloe and Homer are reintroduced, she brings up the fact that he threw up in her tuba back when they were high schoolers and he argues that the tuba belonged to the school.
* ConvectionSchmonvection: Marge, Lisa, Chloe and Barney all get within arm's reach of lava without batting an eyelid.
* 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 [[WesternAnimation/SpongeBobSquarePants SpongeBob]].
* ThisJustIn: Kent Brockman was upset at the reporters who were teasingly dangling his microphone out of his reach.
* TooDumbToLive: A chicken bone causes Homer to choke. A few minutes later, Homer chokes again from trying to eat that same bone.