Moe hires Homer to be his wingman so he can score a date, but Homer ends up being the babe magnet. Meanwhile, Marge is shocked to find that her hairdresser has been dyeing her hair blue all these years[[note]] (despite that the season five episode "Secrets to a Successful Marriage" revealed that Marge "...has been as gray as a mule since she was 17" and that she regularly dyes her hair herself rather than visit a salon)[[/note]] and decides to go gray for a new, mature look.

!! Tropes:
* CallBack: In ''[[Recap/TheSimpsonsS5E9TheLastTemptationOfHomer The Last Temptation of Homer]]'', Mr. Burns tried to deploy a team of winged monkeys but they couldn't fly and he told Smithers to continue the research. [[WildMassGuessing It now seems to have paid off]].
* CharlieBrownBaldness: {{Lampshaded}} when the Simpson kids freak out over how there's no border between their hair and their heads.
* CoincidentalAccidentalDisguise: As Marge goes to find Homer, a series of mishaps gradually make her look like [[Film/TheWizardOfOz the Wicked Witch of the West]].
* CrazyCatLady: The TropeNamer discovers her SpearCounterpart in a Crazy Dog Man.
* SameSurnameMeansRelated: Lisa picks up a supermarket tabloid to read about "[[Music/JessicaSimpson Cousin Jessica]]."
* SeriesContinuityError: Marge is shocked that she's had gray hair for all these years, when the season five finale "Secrets to a Successful Marriage" revealed that Marge has been "...gray as a mule" since she was 17 and regularly dyes her hair herself. Though another question remains: Marge was seen with blue hair when Homer first met her in "The Way We Was" when both of them were high school seniors (or, at least, Marge was. It's implied that Homer is older than her, though he could have been left back due to bad grades). Did she dye her hair then or was this before she started going gray?
* ShoutOut: When a series of accidents made Marge look like a wicked witch from ''Film/TheWizardOfOz'', a flying monkey was briefly seen at the background.