The Morgendorffers move to Lawndale, where Quinn becomes a member of the popular Fashion Club, and Daria meets an equally cynical artist named Jane during a self-esteem class taught by their neurotic, wimpy English teacher, Mr. O'Neill.
The Morgendorffers have just moved to Lawndale from a Highland. It is the first day of school for teenage sisters Daria and Quinn Morgendorffer, so their father, Jake Morgendorffer, drives them to school. Jake stresses that they may have a period of adjustment to their new surroundings, especially for Daria. He goes on to point out that Daria doesn't make friends as easily as other people. Daria questions if he means like Quinn. Jake responds not necessarily and it just may take a while for the other kids to warm up to them.
Arriving at Lawndale High School, Quinn is immediately noticed and greeted by some popular girls, including Sandi Griffin and Stacy Rowe. Stacy asks Quinn her name and Quinn introduces herself. Sandi tells her that she has a cool name. Quinn is then asked on a date by a young man (later identified as Corey). Daria tells her father sarcastically that she will help Quinn adjust.
Jake compliments her on this and after thinking about it, realizes that his daughter is being sarcastic. Daria tells Jake she will see him later and leaves the car and walks into the school without a look or comment from the other students. During the school tour by the principal, Angela Li, Daria displays her cynical side, making sarcastic comments on Ms. Li's statements.
Both girls, as new arrivals, are subjected to a psychological test consisting of inventing a story based on a picture of two human silhouettes. Quinn immediately creates a nice typical teenage story. Daria, on the other hand, gives sarcastic answers to the questions ("A herd of beautiful wild ponies running free across the plains") to the annoyance of Mrs. Manson, the school psychologist. After that, in history class, Daria is able to sum up Manifest Destiny, a task given by teacher Anthony DeMartino. Her correct answer is in stark contrast to the answers of classmates Kevin and Brittany, who say that Manifest Destiny fueled the Vietnam War, "Operation: Watergate," and/or the "Vietcong War," fueling Mr. DeMartino's wrath.
That evening, as the Morgendorffers are having dinner at home, both daughters talk about their day: Quinn is the new vice-president of the Fashion Club and has been invited to join the pep squad. Their parents Jake and Helen congratulate Quinn on her well thought out decision. Daria, on the other hand, only makes cynical observations about her fellow students and teachers. She explains to her parents that her history teacher hates her and that she has some "interesting idiots" in her class. Jake responds enthusiastically to this, Helen interrupts him and says that Daria shouldn't be so quick to judge and make a friend or two.
Daria says that it boils down to trust, and Helen agrees with this. Daria asks her parents if she can borrow either of their cars and they simultaneously refuse.
The school calls regarding the psych test results: Daria has to attend a Self-Esteem Class. The following day, at the self-esteem class presented by the English teacher Timothy O'Neill, Daria is confused by the expressions used. When she asks Mr. O'Neill, he refuses to explain them.
Another student, Jane Lane, tells Daria that Mr. O'Neill doesn't even know the meaning of those expressions used in the class and advises her to relax, further informing Daria that she has already taken the class six times. After school, Daria and Jane befriend each other as they walk home and talk about self-esteem class and other topics. Arriving home, Daria is surprised her mother, Helen is there, having taken the day off to be with her daughter, and they end up going shopping at Cashmans, mainly for Helen's work wardrobe.
The next day at school, Daria and Jane are walking down the hallway. They pass by Quinn who is talking to a boy. He asks Quinn what she likes to do on dates and Quinn responds by listing various options for going on a date. Jane remarks that boy doesn't have a prayer. Daria explains to Jane that Quinn is her sister. The boy asks Quinn if she's got any siblings and she responds by saying that she is an only child. This response causes Daria to get a sour look on her face.
In self-esteem class, Mr. O'Neill discusses with the class about turning their daydreams into realities. He asks Daria what she desires most. She responds that she would want to do something that makes her family suffer. Mr. O'Neill tells her that he guesses expressing such feelings is healthy.
Based on the advice given to her during self-esteem class, Daria convinces her family to go to Pizza Forest, a kids' restaurant where singers, dressed as animals, try to join families in singing: Quinn is bored, and Jake and Helen are uneasy, but Daria seems content with the situation (it is implied that her contentment stems from her family's discomfort). Some days later, as Daria is at Jane's, they agree to use Jane's knowledge of self-esteem exam questions to pass the exam earlier than usual and do so during the following class, answering O'Neill's questions with upbeat and stock answers.
The teacher is so impressed that he decides the girls don't have to continue with the exam and with the girls' graduation three weeks ahead of schedule that he decides to announce it in an assembly. At the assembly, while on podium Jane fakes sudden embarrassment and runs off stage amidst laughter from students. Daria, on the other hand, gives a small speech about self-esteem, concluding with a big thanks for her sister Quinn, in front of all their colleagues (taking revenge on earlier Quinn's statements that she is an only child).
Quinn is furious Daria has addressed her in front of the whole school and, that evening, at home, she raves and dramatically declares she will lock herself in her room for the rest of the life, in typical teenage fashion. This decision, however, lasts only until she takes a call from another male student, Matthew, which immediately lifts her spirits. Having graduated early from self-esteem class, Daria is able to convince her parents to spend even more time together: this time, they attend the UFO convention being held in Lawndale. While Daria is much at easy and Helen and Jake go along, Quinn refuses to enter the geeky space, until being contacted by Artie—at which point she runs to be with her family.
- This is the first of four episodes to have exactly two directors, the others being: Malled, Just Add Water, and Is It Fall Yet?
- This is the only episode in which Mrs. Manson has a speaking role.
- There are four other new students in the first day tour, meaning that a total of six students all started attending Lawndale High that day.
- Brittany Taylor and Stacy Rowe's voices are noticeably different. Brittany doesn't have her trademark high-pitched, squeaky voice.
- The self-esteem class is never seen again during the series.
- Daria's "A herd of beautiful wild ponies running free across the plains" appears to be a shout out to Fawlty Towers: "What did you expect to see?.... A herd of wildebeest sweeping majestically across the plain?"
- Helen's mention of Highland marks the only time the series makes a reference to Beavis and Butt-Head.
- There is a possibly intentional or unintentional reference to Barry Loukaitis, a student who shot and killed his Algebra teacher on February 2, 1996. Corey's line, "Hey, beats Algebra though, doesn't it?" seems to be a direct reference to what Barry said when he killed his teacher ("This sure beats the hell out of Algebra, doesn't it?")
- The first aired episode of Daria.
- First appearance of the show Sick, Sad World, which will be a running gag throughout the series.
- The episode was part of the Daria marathon, Sarcastahon 3000. The episode kicked off the marathon and in the bumper for the episode, Daria and Jane are inside Pizza Forest with Daria in a skunk costume and Jane in a fox costume. Daria describes the episode as "an episode in which a young girl, fresh-faced and dewey-eyed comes to a new town, full of hopes and dreams." This is not the case at all, as Daria never had high hopes for Lawndale, but is done for comedic effect. Jane points out the similarity between Daria's statement and the popular (at the time) show, Felicity.
- The events of Esteemsters are further elaborated on in the Daria guide book, The Daria Diaries. The things about this episode established in The Daria Diaries include:
- Daria had to ride in the moving van because Quinn's clothes took up too much space in the car.
- Daria was made to be a look-out for the movers while they "ran a quick errand in the warehouse district:" (i.e. stole stuff).
- Daria kept the doorknob from her old house in Highland as a memento.
- Daria actually met Trent for the first time during Esteemsters, though it's not seen on screen. Trent also fell asleep in mid-conversation.
- While at Jane's house for the first time, Jane had Daria help her barricade the front door in case the bank tried to foreclose on the house because her parents Vincent and Amanda forgot to leave them any mortgage payments.