When her high-profile start-up Internet company goes belly up, Ellen gives up her high-powered career and heads back to her small hometown to put her life together. She gets a counselor at her old high school and moves in with her eccentric mother and unlucky-in-love sister.
An Internet entrepreneur returns to live in her hometown after her new business venture suddenly collapses.
Now that Ellen has decided to stay in Clark, she has to think what she'll do with her life. Mr. Munn offers her a position as counselor at the school, but she doesn't think it's the right job for her. So she goes to a pond and tries to read the book "Walden", but it's way too boring for her. Later she runs into a suspended student and the two start to throw fruits at Clark's statue and get arrested. While waiting downtown, Ellen talks to the kid, and realizes she might be better in counseling than she thought. Ellen takes the job and becomes the new counselor at the school.
When Ellen finds out that a P.J. Knockers is opening in Clark, she tries to start a petition to stop Clark from being invaded by all the chain stores and lose its small town aspect. But everybody seems blinded by the wonder they think a new restaurant will be. To make things even worse, Catherine quits her job and becomes a waitress at P.J. Knockers, and it takes Dot to convince Ellen to support her sister and ease off on the protest. Meanwhile, the new home economics teacher, Pam, takes over Ellen's office and turns it into a mini bakery room.
Vanity Fair decides to do an interview with Ellen about former dot-commers who went out of business. After everyone tells her to do something about her hair, she finally decides to fix it with Pam and bond with her a little, since they haven't started with the right foot. Ellen's new old-fashioned look doesn't please her as much as she hoped so decides to get another cut. She mistakes the pet shop stylist for the magazine hairdresser and ends up with a dog-style haircut. All that ends up serving as an example for Tina, a young girl who's having personality problems at school.
Catherine feels threatened when she sees how close Ellen and Dot have gotten now that Ellen has moved back home. When Ellen's furnishings arrive from L.A., Dot is so impressed with all of her fancy gadgets and high-style décor, that Catherine is left to wonder what place she will have in her mother's heart -- and her home -- now that Ellen has become the "number one" daughter. So, Catherine makes up a situation that she knows will attract their attention.
Faced with what could be raccoons digging up their front lawn, Ellen calls a raccoon guy to get rid of the problem. Dot, on the other hand, thinks she can take care of the problem herself by scaring the raccoons away with her high-pitched singing. The raccoon guy decides to camp in the lawn, and Ellen discovers Rusty making the holes. Turns out he was just trying to find the time capsule he buried so the raccoon guy wouldn't find it. He made the capsule as a love proof to Ellen, his old high school crush, and just dug it out to show Ellen that he too can do crazy things for love, just like Tug, one of the students who fell for Ellen. But Ellen assures Rusty that they're nothing more than just good friends.
Ellen is wary of Dot's new "gentleman caller" because of her mom's history of falling for the wrong kind of man. Although she tries to find fault with Joe, Ellen realizes that she actually likes the guy -- that is, until she believes she's stumbled upon some startling information about him that she feels obligated to share with her mom. Meanwhile, Ellen desperately searches all over Clark for a decent cup of coffee and ends up finding one in the most unlikely place.
Ellen entices Catherine by telling her how much money she could potentially make by selling her delicious candy, and the Richmonds decide to go into business together with Ellen as the "idea" person and Catherine as the talented taffy maker. But soon Catherine realizes that all the fun has gone out of taffy making now that it has become more of a job than a hobby. Meanwhile, Ellen's fellow high school teachers are dismayed when they realize that the town of Clark doesn't even appear on a local map
When Mr. Munn realizes that long-time school bus driver Mrs. Gibson has reached the school's mandatory retirement age, the birthday celebration turns into a goodbye party. And, to make matters worse, Ellen is called into action to drive the school bus now that the job is vacant. Meanwhile, Ellen thinks her mom is "losing it" when Dot keeps referring to her pet cat, which Ellen has never seen.
Ellen doesn't have any students to counsel, because the entire school seems to be in a good mood. So she snoops around until she finds one student that may need some help: Tug, the football team's kicker. Even though Mr. Munn forbids Ellen to bother Tug, she insists on doing so and approaches his dad, trying to fix a fragile father/son relationship. Meanwhile, Ellen's a little annoyed with the cheap products of the house, a result of Dot's economic way of life. Since she won't take money, Ellen tells Dot she won a $500 prize, which she uses to bet on the football team.
Ellen decides to surprise Dot by flying in her aunt Mary, to whom Dot hasn't spoken in years. Mary buys everyone very expensive gifts, going against Dot's rule of hand made, inexpensive presents. They also fight about Mary's successful career and Dot's way of life. Feeling resented, Mary decides to go back to Chicago, and it's up to Ellen to save the Richmonds Christmas now. She has a word with Dot, who finally decides to accept her sister and leave behind all the hard feelings between them. Unfortunately, there's nothing left to eat, except for Pam's gingerbread house.
Catherine is jealous when Dot gives Ellen a family heirloom brooch. Ellen is excited about the prospect of receiving the elaborate piece of jewelry, but quickly changes her mind when she actually lays her eyes on it. Matters go from bad to worse when she accidentally loses the jeweled creation and must fess up to her mom. Meanwhile, when Mr. Munn appoints Ellen as the new driver's education teacher, she takes full advantage of the situation.
Ellen decides to go Clark's fanciest restaurant all by herself after not finding anyone to go with. There she runs into Catherine, who's on a secret date with Rusty, whom Ellen thought was still hooked up on her since high school. Ellen tags along on their dates, and they decide to break up since it stopped being fun. Their only worry is how Ellen is going to take the break up. Meanwhile, Pam thinks Mr. Munn has a crush on her and Mr. Munn takes advantage of that after Ellen warns him about Pam's feelings.
