Mr. O'Neill encourages his class to pick something to fail at for personal growth, but all they get is misery, grief, and despair; Daria may be forced to supervise Quinn at an upcoming mall fashion exhibit, and Jane is becoming popular enough to replace Brittany as a cheerleader.
Inspired by a rambling and dull seminar by Professor Bentley at a teacher convention, talking about how accepting failure can be a path to future success, Timothy O'Neill instructs his homeroom class to find a task that they are sure to fail at.
Most of the students, however, succeed at failing, thus causing ripple effects throughout their lives, and identity crises: Kevin "succeeds" at "failing as an athlete" and getting kicked off the football team. Brittany "succeeds" at becoming unpopular and loses her place on the cheerleading team. Jodie fails to get her parents to stop overworking her, causing her to be miserable. Jane is able to behave in a conventional manner, to the point of getting asked to replace Brittany the cheerleading squad. On top of that, Daria's machinations to get Quinn banned from going to the Teen Fashion Extravaganza fail—and she ends up assigned to chaperone her at the mall.
Jane, disturbed by how easy it was to be conventional, decides to join the cheerleading team—her confidence is shot and she's worried she might have been kidding herself about being an outcast artist all along. However, she decides against it after imagining herself abandoning Tom and Daria and dating Kevin. Mack and Jodie help Kevin and Brittany regain their places.
However, seeing the damage he'd done has caused O'Neill to have a breakdown and he tearfully declares himself a total failure as a teacher in front of the class. Nobody cares much, with Daria and Jane cheerfully admitting they can't be bothered to intervene. However, Daria finds motivation and visits O'Neill, telling him he was trying his best and that he himself has just failed, and therefore should carry out his own assignment. This random psychobabble works, and O'Neill's confidence is restored. He says he wants to repay Daria... the real reason she helped him, as she's able to make him chaperone Quinn instead!
- Most of the class is asleep when O'Neill explains the assignment. They're then all awake when Kevin speaks, then all asleep again in their next shot, then awake again.
- In the first scenes of Jane as a conventional girl, she has earrings in both her ears. Later in the episode, the earrings are in her left ear only.
- Finally, the Lawndale High faculty are (bar O'Neill) united: in being completely bored stiff with the seminar. DeMartino and Bennett are visibly struggling to stay awake, Barch has already fallen asleep, Defoe is sewing to pass the time, and Li can't believe she's wasting her time.
- This is the only episode that has aired under multiple titles in the US; when it was shown on The N, this episode was retitled '"Fail," due to the term "the f word" being used to refer to a certain expletive.
- Daria and Jane remember, with dismay, how O'Neill once made the class "guess people's identities by feeling their hands".
- This is one of three episodes, along with "See Jane Run" and "Life in the Past Lane", where Jane doesn't have her usual offset hairdo for the complete duration of the episode. It shows that her hair is long enough to make a ponytail.
- Michele Landon mentions Jodie is going to be working at a congressman's office during the summer. This happens in Is It Fall Yet?.
- This includes a rare moment between Trent and Tom: Trent, worried about Jane now she's dressing conventionally, pleads with Tom not to abandon her as "she needs you right now".
- The cheerleaders don't recognize Jane in her new clothes and hairdo. She's been going to school with them for almost three years!
- In rather disturbing responses to the assignment, Upchuck is hunched over behind his chair with a miserable expression; Andrea is drawing herself dead; and Dawn is mournfully reading The Bell Jar, a semi-autobiographical book about clinical depression.
- Jane previously managed to be conventional and popular in See Jane Run, also written by Romberg.
- Mr. O'Neill's neighbors are named after people on Daria staff: Tom Marsan (art director), F. George Fort, Christy Karacas (creator of Adult Swim series Superjail!), and Pat Redding (background design).