At a teacher's conference, Mr. O'Neill misinterprets a speaker's discussion about teaching students that failure isn't the end of the world. With that in mind, he gives his students the task of doing something they know they'll fail at to teach them about how failing isn't as bad as they think.

Jane tries to fail at being a popular girl, Brittany tries to fail at being unpopular, Mack tries to fail at teaching Kevin about the U.S. government, Kevin tries to fail at being bad at football, Jodie tries to fail at convincing her parents to give her time off, and Daria tries to fail at convincing her parents to not let Quinn attend the upcoming fashion extravaganza at the mall.

It goes poorly for absolutely everyone involved.

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!!Tropes:
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* AppealToWorseProblems: Brittany does this with her cheerleader friends in an attempt to become unpopular. She succeeds...meaning she fails the assignment. So she succeeds at failing. Isn't that great?
* ComicallyMissingThePoint: As per usual for Mr. O'Neill, he misinterprets the speaker stating kids should be taught failure isn't the end of the world to mean he should get his students to do something they know they'll fail to see it's not that big a deal. In this case, he views the failure as the end goal of the assignment and not as a possible outcome.
** Sandi overhears Daria's condemnation of the Afghan government's, er, ''famously stringent dress code'' and suggests Stacy beware.
* ContinuityNod: Jake gets a bill from The Doodad Store, introduced in "[[Recap/DariaS1E05 Malled]]".
* DespairEventHorizon: Most of Mr. O'Neill's class becomes horribly depressed thanks to his assignment, and he later crosses the horizon himself realizing the harm he caused.
* JumpScare: Daria has this reaction when she sees Jane in a "popular" getup.
* NiceJobBreakingItHero: Mr O'Neill's idealistic assignment of encouraging students to embrace failure blows up in his face completely. All of his students end up horribly depressed by the results.
** He encourages Kevin to "fail" at being a bad athlete. But when Kevin sees Mr. O'Neill watching him during a big game, Kevin deliberately acts like a bad athlete and screws up the game, leading to a loss for the Lions. The other teachers are not too thrilled with O'Neill.
** Daria succeeds at failing to get her parents to ground Quinn, but her meddling in Jake's anxiety over Quinn's spending leads to Helen ordering Daria to keep an eye on Quinn and the Fashion Club at the mall.
* OOCIsSeriousBusiness: Trent is visibly weirded out by Jane's "popular look" and assumes she's having some kind of emotional breakdown. Tom's also a bit freaked when he sees Jane's wearing a teddy bear backpack, but takes her new look in better stride.
* OnlyOneFindsItFun: During the speaker's presentation at the beginning, the faculty members in the audience are scowling, falling asleep or ignoring him, except for a captivated Mr O'Neill.
* PetTheDog: Mack and Jodie each step in to lift Kevin and Brittany out of the slumps.
* RoomFullOfCrazy: Mr O'Neill's blackboard, before and after his class reports on their assignments:
** Before, it has a bunch of authors, with expressions of glee taken from the letters of their names, e.g. '''E'''rnest '''He'''ming'''w'''ay - Whee.
** After, it has a reading list with crossed-out self-loathing and suicidal expressions, e.g. ''[[Literature/TheSunAlsoRises The Sun (Can Just Go to Hell) Also Rises]]'', ''[[Literature/DeathInVenice Death in (Lawndale) Venice]]''.
* WidowsWeeds: During Jane's fantasy of being on the cheerleading squad, both Daria and Tom are scene in the crowd dressed like they're attending a funeral.