Mrs. Dafoe, the art instructor, asks the talented Jane to submit a poster about student life and submit it into a contest. Jane draws a pretty girl looking into a mirror, with Daria adding a very negative poem about bulimia. The poster does not go over well with the school principal, Ms. Li, who orders it changed and submitted against their will. Daria and Jane don't take this without a struggle.

Mr. DeMartino, Mr. O'Neill, and Mrs. Barch take their classes on a paintballing field trip. Daria and Jane ditch the group to go to a 'great white shark' exhibit that turns out to be a tourist trap, and later new relationships are made (and broken) in tents after it starts to rain.

Quinn writes a paper in Mr. O'Neill's English class that the teacher really likes and recites to the class. Quinn becomes scared that she will now become an outcast because people think she's a 'brain', but just the opposite happens: she becomes a popular brain, and starts to work with it. Daria, meanwhile, finds herself losing her own identity since Quinn is the school brain now.

The Morgendorffers are invited to the wedding of Helen's niece, and Helen insists that her daughters be bridesmaids. At the wedding, Helen keeps getting angry over issues she has with her sister, Rita, whom she despises. Daria, meanwhile, meets her other aunt, the cynical Amy, with whom she has quite a few things in common.

Their old hippie friends, the Yeagers, who haven't changed a bit, visit Helen and Jake. An issue is raised over which family is living the better life now: the laid-back, old-fashioned Yeagers, or the modern, upwardly mobile Morgendorffers. Quinn takes an interest in the Yeagers' aloof, cynical son Ethan, who ends up telling her about their parents' former problems with the law. Daria, meanwhile, heads off to a flea market with Jane, Jesse and her continuing crush, Trent, where they attempt to sell Trent's old records.

Mr. O'Neill assigns his class to make short films. Daria and Jane decide to do theirs on a day in the life of Quinn, the purpose being to show everyone how shallow Quinn is. They get some great footage after Quinn freaks out over her pores, but Daria starts having second thoughts after noticing Quinn actually has some depth.

Daria joins the yearbook staff and takes a liking to the photo editor, Ted, a strange kid who's led a sheltered life under control-freak parents.

Helen and Jake take Daria and Jodie to visit Grove Hills, a private school for A-students. Helen and Jake don't get along too well with Jodie's ultra-conservative black parents, while Daria and Jodie find out the students at Grove Hills are extremely stuck-up. Jodie tells them off, much to Daria's delight. Back in Lawndale, Quinn loses favor with all 3 Fashion Club members, and, afraid to be alone, comes to Jane's house and drives her nuts.

Attending Trent's band's concert, Daria develops a mysterious rash, which comes and goes, and winds up in the hospital.

Meanwhile at the fair, Daria and Jane agree to a ferris wheel ride - with a sobby girl on board with them, too!

In order to prove her P.E. teacher wrong (and to be around a guy she likes), Jane signs up for the track team, where she does very well and becomes a popular track star. However, she starts to find her friendship with Daria fading as a result of her new popularity.

Trent asks Daria to help him find a birthday present for Jane, and the enraptured Daria lets him talk her into getting her navel pierced, which she later regrets. Helen, meanwhile, agrees to accompany Quinn in the ill-fated mother-daughter fashion show.

Daria is asked by Mr. O'Neill to write a story featuring people she knows as fictional characters. She develops a serious case of writer's block, and after several aborted story attempts (including takes on The Graduate and Sense and Sensibility), she starts to lose hope, until Helen gives her some advice. Daria winds up writing a great story about her family in the future.