While Steven and Elyse are away on vacation, the Keaton house becomes a hotel for the weekend after Mallory accidentally crashes her parents' car into a telephone pole and the kids need to raise money for auto repairs. A lot of people are in town for the Leland homecoming game, so Alex decides to take advantage of the situation and rent out rooms but suddenly he's swamped with renters and the house looks like a three-ring circus.

Alex anxiously awaits a crucial college recommendation from his English teacher and urges Steven and Elyse to butter Mr. Tedesco up on parents' nite at school - but the obnoxious Tedesco is so insulting that Elyse slugs him, and a horrified Alex entreats Steven to make amends. The usually calm and non-violent Elyse is amazed and ashamed at her uncharacteristic behavior, though Tedesco ""asked for it"". Steven visits him and after being subjected to disparaging remarks about his wife, winds up repeating her deed. Finally Tedesco, who does recognize Alex's intellect, accepts an invitation to the Keaton home where he alienates everyone again. Alex must decide whether a glowing recommendation from an influential but disgusting man is worth groveling for.

Steven's assistant at the station is bright, talented, funny, witty...and in love with him. And it looks like Steven may be returning her affections. It becomes obvious that Steven's assistant, Stacey Hughes, is very much attracted to him. And after a rough evening at home, as brief fling begins to look better and better to him.

When Alex takes diet pills for a lift during mid-terms, his dependency level increases daily. Alex is studying for several tests and convinces Mallory to obtain diet pills to help him stay awake. At his hyperness and irritability increase, so does his dependency on the pills. When he finally gets so desperate that he threatens Mallory to get more drugs, she becomes worried that he is headed for a ""crash landing"".

While working as a DJ at the school radio station, Alex strikes up a telephone friendship with caller Lorraine Ferrar, who shares his love of swing music, and he and the attractive 40-year-old meet and develop a special relationship. Drawn to Lorraine's sexy voice and love of swing music, Alex invites her to a Big Band concert. On arriving at her home for the date, he's shocked to find that she's an older woman and the mother of one of his sister's classmates. But they develop a platonic relationship, enjoying each other's company and discovering a wide range of shared interests. When Alex and Lorraine continue to ""date"", Steven and Elyse try to accept it but eventually ask her to stop seeing their son.

Alex courts disaster when he invites two dates to the senior prom and devises an elaborate scheme for escorting each of the unknowing girls on a night to remember. Prom chairman Alex is all set to attend the big evening with an ecstatic Rachel Miller, when he finds that his heartthrob, Jocelyn Clark, has just broken up with her boyfriend. While consoling her, Alex invites her to be his date and finds himself in a major jam. With Skippy's help he tries to juggle both dates, until the truth comes crashing down.

Alex is so sure that he will be named valedictorian of his class that he can't cope with the thought of being defeated by a girl especially his girl so his budding romance with Rachel is threatened when she wins the honor. The dismayed and shattered Alex, who even memorized his valedictory speech, feels cheated out of an honor he felt was his destiny all thru high school and he precedes to sabotage his relationship with Rachel.

Alex is thrilled to be taking a college course taught by one of his personal heroes, Professor Ephraim Bronski, but in his eagerness to impress the teacher he gets off to a bad start and is humiliated by his idol when he fails the first class assignment.

Alex is teamed with long-time rival James Jarrett and assigned to work at a ""hotline"" crisis center to fulfill a course requirement, and the two end up in a crisis of their own when they get a call from a suicidal student. As an economics student, Alex finds it demeaning to be forced into a public service position, but his experiences at the crisis center gives him a new outlook on life.

Alex plays Cupid to help his shy pal Skippy get together with Jane, the girl of his dreams, but his good intentions goes awry when the girl falls for him instead. When Skippy and Mallory find Alex locked in a passionate embrace with Jane, Skippy accuses him of stealing his girl.

Because of Elyse's pregnancy, the family decides to get a housekeeper, so Alex hires the lovely Karen Nicholson, a totally incompetent young lady whom the family immediately adores but Steven insists she must be fired. Despite the fact that Karen has no domestic skills and is rapidly destroying every appliance in the house, the kids love her and Steven has a difficult time trying to fire her.

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. The day after she has broken yet another date with Alex to work on her thesis, Lauren complains to him that the project which once thrilled her has become incredibly boring. Having received a lukewarm response from her professor on what she has accomplished so far, Lauren finds the temptation to quit and spend more time with Alex too strong to resist. Alex happily assures her that she is making the right decision.

While Steven fights for his life in surgery, the family fights to remain optimistic about his condition. When Steven's surgery extends beyond the expected five hours, tension in the waiting room increases. A nervous Alex, however, begins to express acute concern only for himself fearing that he has inherited a weak heart, he searches in vain for his pulse. Lauren soon makes Alex realize that he is fixated on his own health to block the anguish he really feels for his father. While the Keatons wait, they receive hope and encouragement from Mrs. Hobart and Mr. Meyers, whose spouses are also undergoing surgery.

Steven battles the physical and psychological aftershocks of his heart surgery. As the hours drag on during Steven's quadruple bypass operation, the Keaton crew grows exhausted in the hospital waiting room. Awakened by Skippy's typically goofy entrance, they all snap to attention when Dr. Harrison appears. He assures them that the surgery has gone well, but Steven must still be observed closely for the next few hours.

The Keaton family unites in crisis when Steven suffers a serious heart attack. While Alex and Andy discuss the upcoming Presidential race, Mallory and Jennifer prepare for another legendary shopping expedition. Moments later, Elyse returns home from jogging, but Steven lags behind, explaining that his run was slowed by a burning pain in his side. Steven dismisses the pain, assuming it was due to something he ate, while Alex kids him that the pain was caused by the guilt of being a Democrat.

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. Nothing is solved at the meeting with the school principal, Dr. Hewitt, the head of the school board and Jennifer's English teacher Mr. Flaherty when the Keaton's refuse to comply with the new school ruling. Jennifer is crushed by the fact that Flaherty, whom she respects and admires, will not stand up to Hewitt and the board even though he claims to be completely on her side.

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.

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. Having responded to an ad soliciting paid subjects, Alex shows up for his first interview and is greeted by the author of the study, pretty senior Psychology major, Lauren Miller. They clash almost immediately over Alex's monetary demands and Lauren's increasingly heated allusions to the emotionally-bankrupt, materialistic attitudes of overachievers like him.

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.

Nick gets back together with his best childhood friend: his dog Scrapper. When Nick's mother moves into a new apartment complex that doesn't allow animals, he is given custody of his boyhood dog Scrapper. Although the lovable pooch is quite old, he's still playful and manages to completely charm the Keatons.

Lauren gets more than she bargained for when she begins counseling Skippy and he falls in love with her. When Jennifer arrives home with her learner's permit in hand and announces that she'd like Elyse to teach her how to drive, a somewhat miffed Steven begins to needle them both about ""women drivers"". With continuous prodding, however, Steven finally gets his way and takes over as Jennifer's driving instructor.

Alex finds himself on an emotional rollercoaster when he's forced to choose between Lauren and Marty. When Lauren returns from her psychology conference, she notices that Alex is acting distant and distracted. After an uncomfortable silence, Alex admits that he has become interested in another woman and needs time to sort out his feelings, a revelation that leaves Lauren angry and confused.

When Alex lands his dream job in New York, everyone's delighted for him, except Elyse. As Steven helps Andy rehearse for his school play on dental hygiene, Alex bursts into the Keaton kitchen with a rousing chorus of ""New York, New York"", and the news that he's been hired by one of Wall Street's biggest investment firms. The family is thrilled, but Elyse is somewhat taken aback when she learns that Alex is expected to move immediately. While everyone pitches in to help Alex get ready, Elyse becomes miffed over a family photo that he packed without her permission and a palpable tension begins to develop between them. In the course of packing, Alex battles wits with Jennifer, accepts fashion tips from Mallory, receives fatherly advice from Steven and shares some final moments with Nick, Skippy and Lauren. All the while, Elyse continues to withdraw from him.

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"".

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. Meanwhile, In an effort to supplement his income from teaching at the ""Y"", Nick naively applies for the job of Dean of Admissions of Grant College. When he's rejected, he lets Mallory persuade him to take the job as janitor of her sorority house.