As the Keaton household gets ready for the first day of the new school year, Alex reminds Jennifer of how incredibly successful he was at the high school she's about to enter, and preps Andrew on the most efficient kindergarten take-over tactics, before leaving for the Leland campus to participate in a psychology research project on overachievers.
Mallory is thrilled to follow in ""Dear Abby's"" footsteps when she's tapped to write the personal advice column in the Columbus Shopper's Guide. She manages to involve the entire family, even Alex, in reading and answering the growing stack of mail, while searching for the perfect letter to launch her career in psycho-journalism. Mallory finally settles on a note from a lovesick teen who signs her correspondence ""First Love"".
While Nick entertains the Keatons with a demonstration of the ""salesmanship"" he's using in his new job selling lightbulbs over the phone, an impatient Andrew waits for Alex to come home so they can watch a special edition of ""Wall Street Week"" together.
Jennifer is appalled when nerdy sophomore Simon Wickerson falls head over heels in love with her. Although Jennifer rejects his advances, Simon is undaunted. He follows her home and tries to shower her with expensive gifts, but Jennifer only has eyes for Roger, a sophomore ""hunk"" who doesn't even know she's alive.
As Elyse wraps up a major project for her firm, she realizes that her busy architectural career is causing her to neglect her family, especially Andy. Although Elyse feels terrible about not devoting more time with Steven and the kids, she doesn't want to give up her rewarding position at the firm.
When Steven arrives home with news of a job opening at his station, an internship position he feels would be perfect for Mallory, he finds his family deeply engrossed in a contest to locate the missing ""Colonel Crackle"" from clues found in Crackle cereal boxes. An excited Alex happily spearheads the search, which offers the winner a 5,000 dollar prize.
Alex and Lauren face the first real test of their budding romance when one of Lauren's former loves comes for a visit and Alex finds himself feeling uncharacteristically insecure.
The Keatons are surprised, but delighted, when Elyse's Aunt Rosemary shows up for a visit. Although Rosemary claims to have sent a letter and spoken with Mallory about her arrival, the mix-up is quickly forgotten as the family warmly welcomes their loving and favorite aunt.
Fearing the long-term effects of Andy's liberal upbringing with Its lack of strong gender identification, Alex tries to push his little brother into learning to play basketball, only to end up in some heated games of one-on-one with Steven.
When Mallory decides to run for student body president of Grant College, her family is surprised at her uncharacteristic interest in politics. She explains that ""it just sounded like a good idea"", and introduces Skippy as the manager of this rather unfocused campaign. Still her most ardent admirer, Skippy encourages the whole family to work on Mallory's behalf.
When Steven's recently divorced brother Rob arrives with his son and daughter for a visit, the Keaton's become a sounding board for their relatives' family problems. In the wake of his divorce, Uncle Rob has given up his job as a CPA and is enjoying ""working in the great outdoors"" as a telephone repairman, a considerably less lucrative career which his teenage daughter Marilyn feels is a great hardship on the family, and particularly on her.
When Uncle Rob's daughter Marilyn stays out all nite with a Marine she meets while visiting the Keaton's, the family becomes painfully aware of her deep-seated anger with her father over her parents' divorce. Rob is left feeling stunned and hurt, as the Keatons begin to realize that communications between their beloved relatives have completely broken down.
When Lauren is required to write a paper on the typical American family, she chooses the Keatons. Focusing first on Steven and Elyse, she asks about their history together and the growth of the family, prompting Elyse to reminisce about her pregnancy with Andy. Steven recalls what a thrill Andy's arrival was to everyone, especially Alex, who was delighted to finally have a brother.
While plans are in full swing for the Keaton's 20th anniversary party, Steven and Elyse are fighting and it looks like they may not make it that far.
The Christmas spirit has come to the Keaton house, where the family is busy baking Christmas cookies when Skippy stops by to ask a favor. He wants Alex to pinch-hit for him as Santa at the mall, and Alex agrees after hearing about the excellent hourly wage.
The Keaton kids are dismayed when the local playhouse agree to stage Steven's radical 60's college play, ""A Draft Card for the Burning"". Embarrassed by the script's laughably dated hippie lingo, they are not surprised when Elyse refuses to reprise her leading role as Sequola Free, the play's sexy activist/anthropology student.
Alex is more than a little sceptical when Nick enters his sculpture "Spirit of Columbus", priced at $200, in an art show at the mall. but when Nick returns with the money and the news that he had several buyers vying for the piece, Alex decides that Nick is completely unaware of the marketability of his work. Appalled that Nick let potential buyers go away empty-handed, he insists that Nick increase the supply to meet the demand and steps in as Nick's manager for a hefty commission.
Alex becomes a deejay of his own college radio show with a program he calls "Syncopated Money", designed to "combine classic American music with an indepth analysis of the business scene". While on the air one day, Alex introduces a tune by "the late blues great, Eddie Dupre", only to discover that Dupre is alive when the legendary blues artist himself calls the station.
Jennifer comes home from school feeling blue because after choosing the American classic "Huckleberry Finn" as the subject of her book report, she learns that the novel has been put on the school board's list of banned books. Although her favorite English teacher, Mr. Flaherty, disagrees with the decision, he informs Jennifer that he must uphold the board's ruling about the book.
While Jennifer steels herself for a showdown with school authorities, Steven and Elyse prepare to back her up in her fight against the school board's book banning policy. Even Mallory gets into the act and shocks the family by falling in love with the forbidden ""Huckleberry Finn"", which she ends up reading aloud to Nick.
While Andy is inspired by his parents' old love letters to try his hand at writing one to a kindergarten sweetheart, Lauren finds herself less and less able to spend time with Alex. She is struggling with her psychology thesis and is becoming increasingly depressed by her lack of significant progress. She confesses to the Keatons that she sometimes has the urge to quit, but Steven and Elyse encourage her to hang in there and keep working on it, much to Alex's chagrin.
As Steven goes thru another one of his dreaded "magician phases" and tries to rope the whole family into participating in his magic tricks, the Keatons get a visit from Evelyn Mitchum, a former neighbor now living in New York, whose daughter Rosalie was beat friend with Mallory in junior high.
As Elyse prepares for her high school reunion, she is contacted by her old buddy, Roger "Eggy" Erdman, a klutzy class nerd turned millionaire. Never a romantic couple, Elyse and "Eggy" made a bizarre team even as friends, since Elyse was the most popular girl in class. She explains to the family that Roger needed someone to keep the bullies away and to save him from his own clumsiness.
While Alex prepares little Andrew's resume for future kindergarten elections, Elyse proudly tells the family that Andy has been chosen as "Buddy for the Day" at school, which means he will be responsible for showing a new classmate around.
Cousin June returns to the Keaton household for a visit after a three year stay in London. All of the Keatons are eager to hear her tales of England, but they just can't seem to let her get a word in edgewise.
Nick again demonstrates his flair for teaching art by conducting a class at the "Y" for children, including Andrew. So popular is the class, in fact, that when the "Y" needs the classroom space back for another program, the kids and their enthusiastic parents are very disappointed. Mallory tells the family that Nick would really like to open up his own art school, and Alex escorts Nick to the bank to help him get a loan.