Facing a lack of funds, Principal Li accepts a generous sum of money from a soda company, in exchange for letting them promote and advertise their product on campus. Daria has a problem with the fact that the school is being used in this manner, however, everybody--the school superintendent included-feels she has no right to complain since the arrangement is bringing the school the money it needs. Unfortunately, Ms. Li fails to meet the profit quota the soda company requires, and is forced to increase promotion of the product, to the point of including it in athletic uniforms and lesson plans. Ultimately the effort to amend the situation proves too much for her, and the soda company is forced to pull out of the deal (though it still leaves its logo in several strategically placed areas).

As the six-month anniversary of Daria and Tom's relationship approaches, Daria starts to feel like Tom is taking her for granted, since they never go out on dates or do anything romantic, like Tom did with Jane. She can't get herself to bring up the issue with Tom, but she talks to Helen about it, and Helen advises her not to expect too much or else she'll be disappointed. She realizes that though Tom didn't realize that the anniversary was approaching, neither did she at first (Quinn had to remind her). Additionally, Tom explains that he's not the romantic type--he did the romantic stuff with Jane only when he sensed their relationship was falling apart. The two of them decide to celebrate their anniversary even though they really don't have to. Meanwhile, Jake joins the staff of an internet start-up company. He is twice the age of the other employees, and never quite figures out what they're saying (they speak in buzz-words and techno-jargon) or what the company actually does. Though

Sandi breaks her leg, and during her recovery gains a considerable amount of weight. Having violated the Fashion Club's strict maximum weight requirement, she resigns her presidency, placing Quinn in charge. Out of respect for Sandi (though partly because Sandi guilt-trips her), Quinn resigns too, but Stacy and Tiffany find it impossible to run the club without them--and their incredibly steep entry requirements prevent them from recruiting any new members. Meanwhile, Daria and Jane--who have been making a series of friendly wagers--make a bet as to whether the Fashion Club will dissolve completely, and they each try to influence Quinn in order to win the bet. Jane--who predicts the club will fall apart--convinces Quinn not to take over as president, but Daria subtly convinces her to help Sandi lose weight. Once Sandi gets back to her original weight, the Fashion Club gets back together, though with a noticeable shift in power.

Daria and Quinn attend a reunion at Camp Grizzly, the summer camp that is the source of nothing but bad memories for Daria. There, Quinn finds that the crowd she hung out with is a little too much like the Fashion Club, and Daria finds that she's too antisocial for her own good--especially after she starts pushing away a fellow misfit, Amelia, who really looks up to her. However, by refusing to follow a crowd, Daria inspires Amelia to stand up to Skip, the obnoxious ""big guy at camp"" whose self-imposed authority everyone is afraid to question. Trent starts getting fed up with Mystik Spiral, and Jane suggests that he give Daria and Quinn a ride to camp, then stay in the woods for a while to think things through. Trent and Jane meet an elderly storekeeper and his wife, whom Trent first thinks are full of country wisdom, but who turn out to be lamebrained purveyors of inedible snack foods. The experience is not a total loss, though, as it provides Trent with inspiration for a new song. He

Daria writes a story that she plans to submit to publication, but is reluctant to let anyone read it. She gives it to Jane and Tom to read--Jane thinks it needs a little work, but Tom likes it and encourages her to submit it. She submits it to a magazine, but it gets rejected. This discourages her, but she decides to give it another go after learning Jake went through a similar situation with a song he wrote when he was her age. The Fashion Club seeks to win a humanitarian award by donating a mirror for the school bathroom, but they first have to get the money to buy the mirror. They decide to start a newsletter and sell it, but get discouraged when all of the fashion predictions they publish turn out wrong. Meanwhile, after learning of the reasons behind her niece Erin's failed marriage, Helen starts to keep a close eye on Daria, making sure she isn't rushing into sex with Tom.

When Principal Li fails to honor the raise promised in the teachers' contracts, the teachers go on strike. Substitutes are hired to take their place, including a spaced-out elderly woman to take over for Mr. DeMartino; and a sleazebag for Mr. O'Neill's class who is soon fired for hitting on Tiffany. That substitute's replacement is none other than Daria. Quinn starts to fear that the truth about her sibling relationship to Daria will come out, especially when she keeps having to defend Daria in front of her friends. Daria tries to teach the class Shakespeare's ""Romeo and Juliet"", and when she assigns a test, Quinn finds that she knows the play well enough to ace it. When Quinn gets a much better grade than the rest of the Fashion Club, Sandi brings up the question of Quinn's relationship to Daria. Quinn finally admits, with no shame, that she and Daria are sisters. While the strike is going on, the Lane siblings end up helping the teachers--Jane by creating posters, and Trent by writin

A gazebo at the Lane residence collapses, and Jane and Trent decide to have it rebuilt because of its sentimental value to their brother, Wind. Jane tries to sell her paintings at an art fair to pay for the repairs, and winds up getting hired to re-create famous paintings for a gallery. Though this becomes financially lucrative for Jane, she gets no creative stimulation from it and contemplates quitting. Meanwhile, Trent hires three slackers to fix the gazebo, and is unsuccessful in getting them to actually do any work. At the art fair, the Fashion Club let a caricaturist draw them, and are so insulted by the drawing that they plan to sue him, a mission that they are persistent at despite Helen's advice against it. Ironically, when Jane and Trent's parents come home, they say that they plan to get rid of the gazebo; and Stacy keeps the caricature drawing because, unbeknownst to anyone else, she liked the way it turned out.

Helen encourages Daria to invite Tom over for dinner, but Daria is reluctant to do so because she fears Jake's erratic behavior will embarrass everyone, especially after he starts obsessing over catching a squirrel that's been knocking over his garbage cans. Helen tells her that she will try to control Jake if Daria invites Tom over. Quinn, meanwhile, decides to find one boy to date exclusively, to show that she is mature enough to do so. Her detailed search for the lucky guy is based entirely on fashion sense, and it's ultimately narrowed down to Jamie, Jeffy and Joey. However, Daria starts playing with her mind and giving her unrealistic expectations for what an exclusive relationship entails (i.e., being together 24/7, adjoining burial plots, etc.), and during the course of a couple of days Jamie and Joey are both dumped, leaving Jeffy the one to come to dinner with Tom. At dinner, Jake's squirrel problems end up causing male bonding between him, Tom and Jeffy, and the three of

Jane starts dating Nathan, a guy whose clothing and lifestyle are extreme vintage retro, mixing elements from the 20s, 30s and 40s. She is charmed at first by his ways, and even starts dressing in retro outfits, though Daria and Tom don't quite share her enthusiasm. However, it soon becomes obvious that Nathan takes his lifestyle way too seriously, and the relationship ends. Meanwhile, Upchuck begins performing magic acts in yet another attempt to attract women. Surprisingly, he is successful this time--he wins Stacy's heart, as well as her participation in a Houdini act he performs for the entire school.

Helen's sister Rita asks her to handle her daughter Erin's divorce, and Helen reluctantly agrees despite the fact that she and Rita never get along. Rita ends up coming without Erin to the Morgendorffers', and as they hammer out the details of the divorce, their usual rivalries start to spring up, mainly revolving around their mother's favoritism toward Rita. Jake is unable to handle all the fighting, and decides to leave the house until Rita goes away. Daria calls Aunt Amy (who is like an older version of herself) to come and help mediate, but Amy only ends up joining in the argument herself. Ultimately, it is Daria and Quinn who help patch things up between the three sisters. The whole ordeal affects Daria and Quinn's outlooks: the talk of divorce makes Daria uneasy about spending time with Tom, while the rivalry between the sisters makes Quinn fear that she and Daria might someday wind up the same way. Meanwhile, Stacy and Tiffany find themselves inadvertently breaking a Fashion

As graduation looms over the horizon, Helen encourages Daria to apply for a scholarship. Due to her lack of extracurricular activities, the only scholarship Daria has a good chance at is one sponsored by the Wizard Corporation, which only requires that its applicants enter an essay contest. Daria's essay makes her a finalist, but she finds herself competing for the scholarship with Jodie and Upchuck, both of whom appear to have a greater chance at winning. Additionally, Daria finds that the corporation has extremely racist and sexist business practices, and as the interviews approach, she questions whether she really wants to pander to their level in order to win. Meanwhile, academic underachiever Jane starts to feel left out. This season has had a running joke involving Jake's failed attempts at cooking. Here, he receives a huge bulk order of hot dogs by mistake and tries to make the best of it.

After a rumor goes around that Daria and Tom slept together, Daria starts to wonder if it is time to take the relationship ""to the next level.""

Daria becomes upset by memories of an argument her parents had when she was a child, which may have been caused by one too many parent/teacher conferences over her refusal to socialize. She later learns that her problems as a kid were just something that comes with being smart.

With high school graduation coming near Daria (now as an adult) is faced with difficult decisions about choosing her college and her future with Tom. Jane has second thoughts about whether she wishes to become a college student.