The Arnolds spend their summer vacation at Lake Wenatchee with the Pfeiffers, with both fathers trying their hand at fishing. Kevin and Paul quickly become bored, so they walk around the small town, when Kevin sees a beautiful young girl. That night they pay Wayne and his new buddy Dave "Wart" Wirtschafter (Scott Menville) for a night at the drive-in, to see Planet of the Apes. There he again meets the girl, named Cara (Lisa Gerber), and he decides to go and talk to her. For the rest of his one week vacation, Kevin spends all his evenings with her, leaving his family and "Mr. Hormones" Paul (and his 25 cent condom) behind, and romance ensues. But, as the holiday comes to an end, the two realize that their summer romance is just that.

It’s Kevin’s first day of 10th grade at McKinley High School. Feeling alone without his best friend Paul, the day goes from bad to worse. First Kevin meets an old 4th grade classmate, Stuart Cartesian, causing a pretty girl to walk away. At lunch, he finds Winnie sitting by herself, but she is soon surrounded by the football team. Then Wayne and Wart give him a "royal flush" because he accidentally stepped on the school seal. Finally Kevin’s U.S. Government teacher Mr. (Arlo) Bottner (Scott Jaeck) begins a vendetta against him when he disobeys "Bottner’s Rules" in class. Kevin rips out a page from his spiral notebook--a sound Bottner despises, and to his surprise, his classmates do the same. He realizes maybe he’s not so alone after all.

After Jack gets him a summer job at Harris & Sons Hardware in town, Kevin dislikes the way his boss treats him. Kevin, Paul, and their new friend Lewis begin hanging out at Hillcrest Mall and they see a classmate, Robby Cashion surrounded by girls while working at the Burger Cage, making Kevin want to work there too. He tries to quit several times, but the old man offers him a raise instead and he feels obligated to stay. Later, when Kevin sees that his father would rather go to the mall because it is easier and faster, he realizes that the world is passing the slow-paced store by. Kevin briefly goes to work at Burger Cage, but in later life he remembers the old-fashioned service ethic that Mr. Harris represented.

Kevin meets Frank Stanavukovic and Denise Lavel, better known as Frank "The Stank" and Denise "The Grease", a couple whose love soared above all others at his high school. However, their longtime romance is on the rocks, and Kevin finds himself in the middle, especially after he helps Denise understand the Jonathan Swift poem "Cadenus and Vanessa" in poetry class. Frank becomes agitated, but soon finds out it’s not Kevin’s fault--it’s his, and he starts to open up to Denise. At the drive thru where Denise works, Kevin has Frank recite poetry, but when that doesn’t work he instead sings a verse from his favorite song "If I Were A Carpenter", which gets their love back on track.

When Kevin has a date his friends Randy and Purdle make fun of him for having his mom drive him and his date around. They turn to Ricky Halsenbach, the first kid in their class to turn 16 and get his driver’s license. Kevin breaks his date to go cruising with his friends on a Friday night, but their glorious night fades when they run into a group of guys in a Mustang who go around mooning people. Then and to top it all off, Kevin runs into his date at Zesty’s Drive-in. Ricky is challenged by the Mustang to a drag race, but dutifully stops at a four-way stop sign. Purdle then moons Kevin’s parents at a traffic light, causing Kevin to flip out. As they decide to go home, the car runs out of gas, but in the end, the guys realize their night out was an adventure and agree to do it again next Friday.

Kevin creates a dilemma with Wayne and his new girlfriend, Sandy (Carla Gugino), after beginning a secret relationship with her while watching an episode of Sonny and Cher. He feels that Wayne is not the one for her--that’s she’s too smart and beautiful for him. But when Kevin notices Sandy making Wayne a better person, he backs off. Kevin asks another girl, Alice Pedermeir (Lindsay Sloane) to the school dance, but she’s already going with someone else. However, Sandy wants to be with the younger more sensitive brother, so she breaks up with Wayne in the parking lot at the dance. Now Kevin is faced with an ultimatum--ditch his brother to be with his ex-girlfriend or comfort his big brother when he needs it the most. Kevin realizes that family comes first, and leaves Sandy to dance with another guy.

When Kevin tries out for the football team and gets cut for being too short and small, he discovers the new sport of soccer, where the school’s misfit team (guest starring Brice Beckham as Nick Bott) welcome him. After meeting the disgruntled coach, Pops "The Bear" McIntyre (Paul Dooley), best known for his championship football days, Kevin joins the team. The players train as best they can, but he soon becomes frustrated with the team’s lackluster coach and their team’s lack of focus. On game day, their high hopes are dashed when faced with a superior opponent. But Pops takes interest again after hearing Kevin’s inspirational speech, and even though they lose 19-0, the team chemistry is what’s important.

Sixth months after their fallout, Norma decides to try to reconcile Jack’s relationship with Karen. The family decide to go out to dinner, for Jack’s 43rd birthday, to Briarcliff Lodge, a restaurant of his choosing, and Kevin decides to secretly treat his family with his summer job savings. However, dinner doesn’t go as planned, when first, the Maitre D’ sits them at a small table, then Jack continues to spar with Karen over her live-in boyfriend Michael. The highpoint of the night is Norma’s photo-album gift, but things go downhill from there. However both stubborn Jack and headstrong Karen feel badly, and reconcile in the end. This makes Kevin realize that what his father really needed for his birthday wasn’t gifts, but his daughter’s goodwill.

The Arnolds’ throw their annual Christmas party, but they notice that things just aren’t as fun as they used to be. Jack’s old golf buddy Lou arrives with his wife, Jeanne (Carol Mansell),but he has now stopped drinking. Al Wannamaker has a coughing attack after Kevin’s impromptu Jimmy Cagney. Jack’s old war buddy Bill Foster arrives with his new young girlfriend Carol (Kimberley Kates) instead of Marsha, his now ex-wife. To top it all off, "The King of Lawns" Ed Ermin is caught smoking marijuana in the basement. Kevin and Wayne are sent to the supermarket, and on return they find their parents alone and curled up by the fire - they realise too that the old days are gone, and the older Kevin narrates that this was the last such party they held.

Tension arises between the Arnolds and the Pfeiffers after Alvin (Paul’s father) makes an enormous amount of money by investing in beach front property; and Jack, out of obvious jealousy, is irked by Alvin’s spending spree: a color TV with remote, a ride-on lawnmower, a swimming pool, and a country club membership. This situation also puts Kevin and Paul’s friendship on edge as well, heightened when he learns that Jack also could have joined the investment deal. At the county club, the "cold war" continues until Norma graciously proposes a good will toast celebrating the Pfeiffers’ success. However, Alvin begins sobbing and tells everyone that he has, in reality, lost everything. Back home, Kevin decides to meet Paul and they patch things up, and we learn that Paul is leaving the prep school and coming to McKinley High. (NOTE: As per producer and episode writer Mark B. Perry in the DVD extras, this episode was erroneously titled "Pfeiffer’s Choice" in many online episode guides.)

Kevin seems to be a natural at driving, however, there’s one problem--his inability to parallel park. This troubles him in driver’s education class, especially when other student drivers, under the watchful eye of Coach Meecham (Michael Gregory), have no problem with it. Jack allows him to drive down-town, but he freezes up when told to parallel park in front of the shops. His nerves build until he lies about not getting his driver’s license, even though they celebrate by giving him a cake and spare keys to the car. Determined to secretly practice, he tries to use the car that night, but only ends up running over the lawnmower. His father comes out to see what’s up, and Kevin finally confesses all. In the end he gets the licence with his father’s help, but is grounded for a month afterwards as punishment.

After getting into several recent accidents leading to a license suspension, Grandpa Albert Arnold refuses to listen to his family’s concerns and stop driving while suspended. Frustrated, he finally asks Kevin to drive him back home, but resumes driving the car a short time later anyway. Their road trip takes many unexpected turns as Grandpa wishes to relive travelling to his favorite diners and roadside attractions. For the first time, Kevin notices Grandpa’s old age creep up on him, and while reminiscing about the old days and not paying attention to the road, they nearly crash the car. Albert finally accepts he’s getting too old to drive and lets Kevin buy his 1965 Oldsmobile Cutlass for a dollar. Now, Kevin will always remember his first car because it was his grandfather’s last.

Kevin’s new English teacher, Miss Shaw (Lanei Chapman), is a young active teacher fresh out of grad school. In her idealism, she decides not to adhere to regular teaching practice - a move that makes her well liked among most of her students, including Kevin. While the class enjoys her unorthodox curriculum and grading system ("Ps" for pass, and "F" for fail), it doesn’t sit well with the parents and the school principal Dr. Valenti (Richard Fancy). He informs her she must conform to departmental guidelines, and thinking the young activist in Miss Shaw will take on the might of system, she surprises Kevin when she states that "It’s just not worth it" and quits, leaving Kevin unsure of what to make of it.

While cramming again for his SATs, Wayne begins to give up on the prospect of going to college. Meanwhile, Kevin thinks of his own future when his guidance counselor, Mrs. Ruebner (Pat Crawford Brown), also urges him to start planning for college. Finally, rather than taking the tests again, Wayne, along with his buddy Wart, decides to join the army instead. With the Vietnam War still going on in 1972, the family is afraid that Wayne could be shipped off to fight. Although Jack objects to his son’s decision, Wayne (as an 18-year old) is an adult now, and he allows him to go and take the physical. However, Wayne is rejected due to psoriasis while Wart is accepted, then sent to basic at Fort Polk in Louisiana, and two months later, shipped off to Vietnam.

Kevin is caught between spending time with Julie Aidem, a girl he’s been dating, and hanging out with the guys. Although Kevin admires Julie’s cool dad Ben (Lyman Ward), he notices that her mother June (Sandy Faison) has him on a short leash, and he soon realizes Julie is doing the same with him. Suddenly Kevin feels trapped, and he ditches Julie to play football with the guys, but she shows up at his house, then wants them to go steady. But Kevin can’t bring himself to announce it in front of her family, especially after Ben tells him about his old black lab Duke that ran away the day he proposed to June. He then breaks it off in front of her family, and returns to doing what most 16 year-old boys do - hanging out with the guys.

Kevin has a crush on the new Swedish exchange student Inga Finnstrom (Shevonne Durkin), and asks Winnie to introduce her, and in return, she asks Kevin to help her meet Matt Stevens. Things seem to go well initially, but become awkward when Matt suggests they double date for the spring formal. On the way there, tensions rise between Kevin and Winnie, until Matt asks Inga for a dance leaving Kevin and Winnie alone on the dance floor. While slow dancing, something strange happens and they are soon brought close together once again. They then ditch their dim-witted dates and go to the point to park, but both find it hard to make a move and wind up kissing one another on the eye. Both understand that they need some more time, particularly since there is still much they have yet to learn about themselves.

McKinley High’s basketball team is having a great season thanks to their star player, Bobby Riddle (James Caviezel) and make it all the way to the state championship of 1972. Kevin and his school are caught up in the euphoria. Jack, however, is more practical, telling Kevin he needs to focus on his studies instead. On the night of the playoffs, Jack decides to accompany Kevin to the game. He enjoys the first half, but Kevin is annoyed when the team loses and is embarrassed when Bobby tells him to leave him alone. On the way home, at a diner, Jack teaches Kevin a valuable lesson he never forgets, when he says "It’s not easy being a hero."--his father wasn’t talking about Bobby, he was talking about himself.

Kevin recalls a typical lunch period at McKinley High--academic crises, romances, and problem-solving. For example, Kevin is asked by Winnie to donate blood, while Ricky has to complete a thousand word paper on the A Day in the Life of a Citizen in Ancient Rome. Paul gets sloppy Joe sauce on his white pants right before a big debate, and Chuck wants to ask Shelia McCaffry out on a date, but when he finally does, his constant twitching turns her off. Wayne tries to win a $20 bet by finding the name of a kid known only as "Maniac" -- he succeeds but "Florence" threatens to kill him if he tells. Kevin is also pressured into ditching school to see The Devil in Miss Jones with three troublemakers, Jimmy Donnelly (Seth Green), Joey Spinoza, and Neal Pemish, but they are caught by Dr. Valenti and blame Kevin -- only for Winnie to save the day when she mentions donating blood.

Kevin and his friends plan to sneak in to see the R-rated movie Carnal Knowledge with Ann-Margret, their first film with erotic scenes. Paul reveals that he will be having dinner with his mother’s old college roommate and her college-age daughter Beth (Kawena Charlot) that night and can’t make it. After Kevin, Ricky, and Chuck sneak in then get kicked out of the theater, Paul tells Kevin that he had his first sexual encounter with Beth, leaving him confused at exactly what happened. At first Kevin is upset when Paul doesn’t disclose any details, then he inadvertently reveals Paul’s secret to his friends. However, when Paul confesses he can’t cope with a casual relationship, Kevin helps and takes him to the airport to say goodbye to Beth. Even though Paul doesn’t meet her, he still appreciates Kevin, his long-time best friend, who’ll do anything for him.

When Kevin’s parents go away for the weekend, and Wayne leaves the house too, the guys convince Kevin to let them come over. When their poker game becomes boring, Chuck decides to invite a girl he likes, and Ricky also steps up and invites Alice. Unfortunately for Kevin, they also bring or invite their own siblings or friends, soon turning the Arnold’s house into a crowded wild party. As supplies run low, Kevin and Chuck make a food and drink run to a liquor store, but the clerk (Michael G. Hagerty) doesn’t fall for Chuck’s fake ID. When they get back, the party’s totally out-of-control and the house is trashed. Kevin futilely spends 3 hours cleaning up afterwards, but his parents come home early and bust him. Seeing the mess, they automatically blame Wayne. He surprises Kevin by taking the heat for the mess, and Kevin then washes and waxes his car in return.

When Karen comes back home in the middle of the night, the Arnold family soon learn she and Michael had a fight, and of her plan to move back home. She asks Jack to collect her things from the house and Kevin and Wayne are soon roped in too. After collecting her things, Jack tells Michael he didn’t want to see them living like this, but Michael divulges the reason for the fight--he had asked Karen to marry him. He then follows them home to see Karen, but she again rebuffs his overtures since she doesn’t believe in the "antiquated, male-centered institution" of marriage. She asks him to leave. However, when Michael comes back with his tent and pitches it on the front lawn, he stands in the dark in the pouring rain waiting for Karen to come out. Eventually, Karen realizes how much Michael loves her and goes outside to make up--and ten days later, she asks Michael to marry her.

With their wedding day approaching, Karen and Michael, despite Norma’s enthusiasm, decide against a traditional ceremony. Instead they plan a hippie wedding with an Indian Maharishi and all their friends in the backyard. However, Kevin, becomes restless when Michael confides in him he got a job in Alaska and they are planning to move there right after the ceremony. But Karen has yet to find a good moment to tell her parents, and when Jack makes a touching speech, her friend Earth Mother delivers a cake that says "Alaska or Bust" on it. In the confusion and tension, Karen then tells her parents she and Michael have their own life, and they have to let them go and live it. They agree, particularly when Jack recalls that he took his own bride far from her family. Jack and Norma then allow their first-born daughter out into the world, reminding her that irrespective of where she is, they will never let her go.

As summer starts, Wayne gets a job on the loading dock at Jack’s company, NORCOM, and Kevin is frustrated to be missing out on a relaxing summer since his parents are pressuring him get a summer job too. With Winnie working at a diner, Paul an assistant manager at a Chinese restaurant, Kevin finally takes a remedial position there too. While cleaning his room, he finds a card from Cara, his summer love from last year, and on the way to work with Paul, he spontaneously decides to go back to the lake and visit her. But Cara isn’t thrilled to see him and wonders why he’s there since he never replied to her Christmas card. She leaves, and the next day (the boys having spent the night in the car) tells Kevin that she has a boyfriend. Kevin then wonders why he ever ran off in the first place, when he still has Winnie.

When Winnie thinks Kevin is flirting with a waitress (Sarah Dammann) at Fatso’s drive-in, she gives him an icy reception and leaves him to sit with her friends for the rest of the night. Even though Kevin explains that it was just a misunderstanding, he remembers back to a lot of ups and downs he had with Winnie and with the girls he knew in his past. Although his friends and Wayne try to help him out, it’s no use, and he has to patch things up with Winnie himself. By the end of the evening, Kevin speaks from his heart by telling Winnie that she’s the only girl he ever cares and thinks about. But Winnie’s heard enough and takes Kevin into her arms with a passionate kiss--all she wanted to hear was some honesty.