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 and it is the first day of school for teenage sisters Daria and Quinn Morgendorffer, so their father, Jake Morgendorffer, drives them to school. He stresses that they may have a period of adjustment to their new surroundings, especially for Daria. Arriving at Lawndale High School, Quinn is immediately noticed and greeted by some popular girls, including Sandi Griffin and Stacy Rowe, and asked on a date by a young man (later identified as Corey), while Daria 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 the pep squad, while Daria only makes cynical observations about her fellow students and teachers. The school calls regarding the psych test taken: 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 their meaning and advises her to relax, further informing she has already taken the class six times. After school, Daria and Jane befriend each other as they walk home and talk calmly 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, mainly for Helen's wardrobe.
The next day, prompted by O'Neill's advice during self-esteem, Daria convinces her family to go to Pizza Forest, a kid's 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 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 at 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 to attend Lawndale that day.
- Brittany and Stacy'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 Sick, Sad World
- 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 esablished 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 Mr. and Mrs. Lane forgot to leave them any mortgage payments.