* EsotericHappyEnding: Tony gives up what was practically his dream job (as a college baseball coach) because Angela was unhappy in the small college town Tony coached in, practically hitting the ResetButton.
* HilariousInHindsight: In the episode where Jonathan's first girlfriend gets a crush on Tony, he utters the line "I never want anything to do with girls again". Cute then, but it becomes utterly hilarious since Danny Pintauro came out.
* ShippingBedDeath: Though by the time Tony and Angela got together, this was more a symptom of the show's demise than a contributing factor.
* ValuesDissonance: These days the show's very title comes off as absurd; Tony is Angela's employee and their genders have nothing to do with it. This was mocked in ''{{Community}}'' when a professor devotes his career to analyzing the titular question, only for Abed to deflate him with a lengthy lecture about why Angela was unquestionably the boss.
** And on the ''{{Roundhouse}}'' episode "TV On Trial", where the answer to [[UnresolvedSexualTension "the question America has been asking for nine torturous years"]] [[BaitAndSwitch is actually an argument between Tony and Angela]] (played by David Sidoni and Shawn Daywalt) over who is the boss.
** Actually, wasn't it Mona who hired Tony on Angela's behalf? That would make her the boss.
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