In the remaining days of summer, the Arnolds decide to take a vacation trip to Ocean City, in part for old times’ sake, since it was Jack and Norma’s honeymoon destination. Paul comes along, but the vacation turns out to be a disaster, as Paul gets car-sick and throws up a couple of times, gets sunburned and develops an allergic reaction to fish he ate, which forces him to stay inside for the remainder of the week-long vacation; add to that Wayne’s constant bullying, Karen’s belly-aching and complaining, and Jack’s constant complaining about the high prices. So Kevin, now feeling more alone than ever, decides to take a stroll along the beach in search of a little solace, where he encounters Teri (Holly Sampson), a beautiful (although older) girl who also seems alone, but more upbeat and optimistic. Kevin and Teri plan a date to the boardwalk arcade the next day. Their date ends with a kiss under a pier, but the moment is ruined when Teri turns down a second date for the next day, because she and her family got called back home to Albuquerque due to her father’s job. Teri promised to write to Kevin every so often until they met again; but after only one letter, Kevin never heard from her again.

As Kevin begins eighth grade, he finds himself struggling in math and quickly has trouble understanding it. But when his very strict math teacher Mr. Collins (Steven Gilborn) offers him a study group after class, Kevin refuses. Kevin then receives bad grades on pop quizzes and fails a test. Eventually, he must tell his dad about the situation and he starts to turn things around.

Wayne gets his driver’s license but reluctantly has to chauffeur Kevin and Paul to the mall. While there, Kevin meets his "dream girl" (Jennifer Barron) whom he follows to the movie theater where Romeo and Juliet is playing. When Kevin finally gets his chance to introduce himself and talk to her, Wayne shows up and embarrasses him by driving away every time he reaches for the door handle.

Against his mother’s wishes, Kevin decides to play "no equipment" football in Shepherd’s Park with his friends after school. After finding blood on his shirt, Norma (Alley Mills) tries taking Kevin clothes shopping to distract him from playing, but it backfires. Kevin soon realizes that this game is dangerous when he gets hurt while being gang tackled and has to bandage his wounds himself.

The new dramatic arts teacher Mr. Weber (Nicholas Hormann) is holding auditions for the school play Our Town and Winnie gets the leading role while Kevin and Paul are in charge of working the spotlight. When Paul’s nerves get the best of him, it’s up to Kevin to run the spotlight, which he awkwardly does until Winnie’s moving performance inspires him and leads her father to move back in with her and her mother. Somewhat of a reworking of "Our Miss White".

After a heated argument over their elusive Willie McCovey baseball card trade, Kevin and Paul choose new best friends. They go their separate ways, only to realize, after their new friends ditch them, they missed each other’s companionship in the end.

The Arnolds notice one of their neighbors driving home a new car, while the Arnolds’ family station wagon just isn’t reliable anymore; so in "keeping up with the Joneses," they decide to buy a new car, too (after Norma pressures Jack into doing so). They go to a car dealer and, at the persuading of the salesman (and the kids), Jack selects a new cherry-red ’69 Ford Mustang convertible and is ready to seal the deal. However, Jack blows up and backs out of the deal when he thinks the dealer is not offering him a fair trade-in value for their old car. Meanwhile, Jack decides to fix up and wash the station wagon and put it up for sale. But when Jack informs prospective buyers of his price, they walk away laughing, thinking the price is outrageously high--which leads to Karen offending her father by calling him "cheap". However, in the end, the Arnolds do end up buying a new car, but it’s not the Mustang. It turns out to be a 1969 Galaxie 500. The station wagon ends up being towed away to the junkyard.

Kevin gets his first pimple a few days before family friends, the Pruitts and their beautiful daughter Gina (Heather Green), come for a visit. As he desperately tries to get rid of his pimple, Kevin goes as far as paying Wayne for his zit cream to covering it with a band-aid and telling Winnie he got into a fight with school bully Tony Barbella (Tony Nittoli). Unfortunately for Kevin, none of these tactics work, and Kevin must face the music—and the Pruetts—with his pimple, only to discover that coincidentally Gina had developed her first pimple, too.

Kevin overhears classmate Eddie McCormick (Chris Demetral) having a conversation with two others about cheating in his math class. After being graded on a curve because of the cheaters, Kevin decides he wants in and asks Eddie "How ’bout those Mets", the secret code that he’s on board. As a result, his grades rise to near perfect and he is put in the honor math class. After being unable to keep up, Mr. Collins (Steven Gilborn) offers Kevin to revert to his old math class and keep his grades up.

After helping the new student from San Francisco, Larry Beaman (Joshua John Miller), get out of trouble with vice-principal Diperna (Raye Birk) when he’s not allowed to play his guitar on school property, Larry teaches Kevin how to play guitar. Inspired by The Beatles and Jimi Hendrix, they form a rock n’ roll band called the "Electric Shoes" and land a gig at an 8th-grade birthday party for Amy Ermin (Stefanie Scott), but are forced to stop playing by her father (Ben Slack) and the police because they’re too loud.

Both being dateless, Kevin’s lab partner Linda Sloan (Maia Brewton) suggests that she and Kevin go to the school dance "as friends". But after he agrees, his crush Susan Fisher (Kelly Packard) asks him to save a dance for her and Kevin is now torn between two dates for the dance. At the dance, Kevin lets Linda dance with Steve Padway (Andy Howard), a boy who likes her while Kevin gets to dance with Susan, but has nothing to say to her afterward and she gets back with her boyfriend Donald Wallach (Sean Wohland). Kevin paid so much attention to Susan that he hurt Linda’s feelings and is left standing by himself at the punch bowl. After a short break-up, Paul and Carla get back together, making Kevin feel left out. Now alone, Kevin searches for the right one—Winnie—but they just miss each other and he leaves the dance.

Grandpa Arnold (David Huddleston) visits Kevin and his family and he comes bearing gifts. One is a surprise for Kevin—a puppy, but Jack doesn’t think he can handle the responsibility of taking care of an animal. After an argument with his father, Jack decides that a dog is exactly what they need and asks Kevin to keep him, naming him Buster. (Gary Grossman) guest-stars as Kevin’s biology teacher Mr. Corey.

When Paul gets dumped by Carla, Kevin wants to help his brokenhearted friend get his self-confidence back. Kevin convinces Winnie to ask Paul out on a date, but after going out three times, things take an unexpected turn when Paul actually starts liking Winnie, making Kevin jealous. Winnie doesn’t feel the same way and tells Paul she still likes Kevin, but to keep it a secret. Kevin finds out and goes to Winnie’s house to say that he knows she’s "crazy about him", only to get the door slammed in his face.

Things get complicated for Kevin when his "please forgive me" valentine meant for Winnie ends up in the locker of Becky Slater who, because of it, wants to resume their short-lived romance. But Kevin tells her the truth and breaks up with her yet again. However, Becky wants revenge again and tries to run Kevin off the sidewalk with her bike but Curtis Hartsell (aka Cupid) (Ben Savage) gets in the way and she crashes into Craig Hobson, making a love connection. Kevin seeks advice on love from Mrs. Heimer (Miss White) and she tells him to speak from the heart which he does to Winnie, finally confessing that he likes her. Guest-starring: Elyse Eberstein as Winnie’s friend Melissa Bemil and Jean Palmerton as Kevin’s art teacher Mrs. Dougherty. Part 2 of 2

At school, Kevin sees his friend’s face after he receives "the talk" from his father and wonders when his time will come. Since it’s Jack’s week off, he has nothing to do but repairs around the house, which upsets the balance of Norma’s household. She suggests that he and Kevin build a tree house together. Jack finally lets Kevin help by allowing him to use his power tools and things run smoothly until they go up on the platform to look at the view of the neighborhood. They catch a glimpse of their voluptuous neighbor Donna (Janet Wood) singing while digging in her tomato garden from above and they share an awkward moment, especially when Norma invites Donna over. Norma eventually decides to check on their progress and sees the same view of her neighbor. Jack then has a different talk with Kevin and says he’s too old for a tree house, which stops the construction altogether.

When Kevin’s chorus teacher Mr. Frace (William Lanteau) hands his class over to perky student teacher Miss Haycock (Andrea Walters), the untalented, terrible-voiced 8th grade glee club has to perform "Stout Hearted Men" in the Spring Sing concert. After Kevin and the rest of the class tells Miss Haycock they don’t want to sing in the recital, she breaks down in tears; but classmate Warren Butcher (Jeffrey Baum), who never talks, begins singing in perfect pitch. Now they have a secret weapon for the concert--until the night of the concert when his 13-year-old voice starts to change midway through the song.

Since Kevin and Winnie are a couple once again, they get invited to a make-out party hosted by infamous 9th grader Robbie Hudson (Greg Davis). When they get selected to go into the make-out room, things get awkward for the young couple, especially when Winnie doesn’t want to kiss Kevin, leaving him confused. Later in the night, Winnie comes to Kevin’s bedroom window while he’s sleeping to go for a walk so she can explain herself. But Kevin thinks Winnie wants to be just friends again--until she calls him her "boyfriend" and kisses him on a bridge. Turns out that Winnie was only waiting for the perfect moment!

It’s tax time, but Norma loses the tax receipts needed for filing, and the family awaits their impending doom when Jack finds out. But they learn there are more tragic things happening in the world. The news broadcasts of the failed Apollo XIII space mission has everyone on edge, so Norma goes to a church to pray for the missing astronauts. In a subplot, while in creative writing class, Mrs. Stebbins, (Salmone Jens) Kevin’s English teacher tells him to write an obituary of his life but he can’t decide how his life will turn out in the future. Guest Starring as Kevin’s classmates: Emily Schulman as Susan Kelly, Josh Berman as Harold, Billie Joe Wright as Larry, and Michael Bower as Joe.

When Paul tries out for the Kennedy junior high Wildcats baseball team, Kevin gets the coach’s attention when he instructs him at bat. Coach Ted Baker (Harrison Page) asks Kevin to come up to bat and he smashes a line drive to right field, impressing him so much he asks him to try out for the team. But Kevin wonders why he keeps making the cut even though his performance is bad and wants to know why. He finds out that Coach Baker is his father’s old Marine Corps buddy in the Korean War. Jack starts going to Kevin’s tryouts and talks with the coach, but when Kevin sees his name crossed off the cut list, he’s relieved that he wasn’t receiving favoritism after all. He hits one out of the park, pretending like he’s Bobby Thomson of the New York Giants baseball team in the National League pennant game of 1951.

When Kevin asks his beloved algebra teacher Mr. Collins how he is doing overall in math, he doesn’t get the response he needed to hear back. Instead, Mr. Collins gives Kevin private tutoring to raise his grades of C’s on quizzes into A’s on tests. Mr. Collins then suddenly canceled a scheduled session several days before the mid-term exam. He also took the next few days off but would be back to give the exam or leave it at the end of the week, leaving Kevin to fend for himself. Kevin thought Mr. Collins was helping him because he believed in him and was his friend, but he stated he was simply his teacher. On the day of the exam, Collins does show up with the exam that Friday, so Kevin decides to get a "respectable F" and botch the answers on purpose. The following Monday, Mr. Diperna (Raye Birk) informed Kevin and the class that Mr. Collins died from heart failure. It seemed the teacher knew his end was very near (he likely knew this for some time) and at home that weekend he "misplaced" his test before passing away. It seems that Arthur Collins believed in Kevin Arnold after all.

The most popular girl in school (Lisa Berlini) makes a list of categories she thinks is the definitive rating of 8th grade boys called the "Lisa Berlini Poll." Kevin is chosen for "best eyes," while Paul’s self-esteem falls when he is named the "brainiest". The boys then decide to retaliate by making their own poll about the 8th grade girls; but when Paul makes the unlikely choice of Kevin’s mom for "best smile," he is embarrassed, especially when his friends all agree. Paul then develops a crush on Norma when she says he looks "manly" with glasses, but she handles it well. Paul and Norma then go to a chamber music concert together and when he gives her a rose, she lets him down easy with compliments of finding other girls his age.

With Karen’s 18th birthday approaching, tension arises with Jack when she tells him that she wants to enroll in a liberal college. When he declines her decision about her future, she suggests taking a year off to go backpacking in Europe. In the end, Jack realizes that his little girl isn’t so little anymore. Karen’s leaving and won’t be back next year, but he sends her off with one last gift--his military "kit bag" from the Marine Corps, so she can use it for college or if she goes some place. Karen then blows out her birthday cake candles, makes a wish, and goes out for the night, with her father leaving the porch light on when she returns.

When Jack finds dry rot in the basement, he talks about selling the house, sending Kevin in a panic. He tells Winnie and Paul that he’s moving, but is surprised they take it well and are ready to have a long distance relationship. In the end, Jack realizes that he’ll just get the basement fixed, but accidentally slips that the Coopers are moving 4 miles away across town. Kevin is now in despair over this and wonders why Winnie didn’t tell him, especially that she’s going to a different school at Lincoln Junior High next year. Thinking she’ll stay if he buys Winnie a ring, Kevin gives it to her but she can’t accept it and breaks up with him instead, making Kevin throw it in the trash. On moving day, Kevin decides to say goodbye to Winnie and finds her alone in the moving truck with his ring in her hand and they have a long hug. Then Kevin’s off to Karen’s high school graduation and the family celebrates with Wayne at his new job as a waiter. Now Kevin has to travel way beyond his front door and out of his neighborhood to see Winnie; his world just got a little bigger.