Kevin, is now in the 11th grade, alongside Winnie his girlfriend, and Paul the class president. Bored, he is becoming a wise guy in class like his new friend, Jeff Billings. After the school’s rival steals his school’s knight mascot, Kevin tries to make a name for himself when he steals then frees their owl mascot. Kevin is also now the delivery guy at Mr. Chong’s, and has to advertise the business on his car, making Winnie embarrassed to ride with him. Wayne now works in the mailroom at NORCOM, and lives in the family’s basement. Meanwhile, Wayne’s old buddy, David "Wart" Wirtshafter, returns home from a tour in Vietnam a changed man. But he doesn’t feel welcome at the big game when an anonymous shout of "murderer" is directed towards him. They later find Wart sitting alone with his clothes on the ground in a neat pile. He says nothing seems to fit any more, but he wasn’t talking about the size of his clothes, so Wayne offers the shirt off his own back.

Kevin and Wayne are taken by Jack to Berlinger Falls, a secluded fishing hole for their final tri-annual fishing weekend trip and some male bonding. However, the woman at the bait shop tells them they closed the road there, and Jack’s once beloved secret spot is now isolated and overgrown. Kevin is annoyed that Jack and Wayne still treat him like a child, joking at his expense and rebuffing his attempts at having a beer. Irked, Kevin tells his father that his lifelong dream of building a retirement cabin in the area is never going to happen. Things go from bad to worse when Wayne and Kevin start fighting, causing the old tent to go up in flames. But by the next morning they figure out why they came here in the first place: to say goodbye to a time and place full of shared memories.

When Candy Jensen, the daughter of Jack’s boss Arthur, is getting married, the whole family gets invited. At the reception, Wayne tries to talk with Candy, but since they dated, she acts like she doesn’t know him. Jack is frustrated with Arthur, who has been flirting with Norma the whole night. Kevin tries to impress a girl he just met, Linda, when he says he can get champagne, and she tells him to meet het at the gazebo. In the end, he is stood up by Linda and gets drunk on the bubbly. Jack has finally had enough of Arthur’s overtures, and tells his boss to get his arm off his wife or he’ll break it off, finally getting to dance with Norma. After the groom’s final speech Wayne tells Kevin that even though the groom had "waited" until he got married, the bride certainly didn’t.

Despite having an after school job, Kevin’s financial problems are taking a toll on his life. When his young and beautiful history teacher, Miss Farmer (Rebecca Staab) posts an ad on the school bulletin for a painting job, he quickly accepts. Thinking it’s going to be easy, she informs him that she will pay him $500, but he needs to paint the whole exterior of the house. Kevin realizes he has to find a crew to help him tackle this time consuming job, so he desperately recruits Jimmy Donnelly, Joey Spinoza, and Eddie Horvath (Jeremy Davies). Between their pay and the cost of paint and supplies, Kevin’s cash soon disappears. He is further frustrated when the prepaid hired help suddenly quit, leaving him to finish the job done alone and at a loss. He then learns that Miss Farmer sold the house to Mr. Kaplan (Jack McGee) another person she manipulated, and Kevin learns his lesson, namely of being taken advantage of by a pretty lady.

When Kevin’s high school holds a debate for the McGovern/Nixon presidential race, the students don’t seem to be interested until Mike Detweiller (Lance Guest), a charismatic speaker heading Senator George McGovern’s local campaign, gets everyone’s attention with his anti-establishment view. Winnie enthusiastically joins the McGovern campaign committee, but Kevin is unconvinced, believing that Mike has a romantic interest in her. Suspicious, he breaks in to campaign headquarters late at night to catch them together, but it turns out to be a meeting with McGovern himself. The next day, seeing the early promising returns, Kevin goes to celebrate with the team, but it was premature as Nixon soon wins convincingly. He arrives to find Winnie upset and Mike leaving with his assistant Peggy. It seems he wasn’t interested in Winnie after all, just wanting to harness her enthusiasm to encourage young people to become more politically motivated. Kevin states from that point on, Winnie would remain a liberal.

Kevin is feeling pressure from the guys in the locker room to reveal intimate details of him and Winnie, since they have been going out for 6 years. Kevin plans to be alone with Winnie when his parents take a trip out of town for one night, so he asks her over to study for the SATs. Surprisingly, she agrees, and even though Kevin creates a darkened romantic atmosphere, Winnie still wants to study, but finally figures out Kevin’s intent. Despite his attempts at intimacy, they end up doing what they always do--reminiscing about their past. They end up falling asleep together on the couch and Kevin panics the next morning. After Winnie tells her parents where she was all night, and how much they trust him, Kevin feels frustrated. The guys catch wind of his mood and Kevin tells them to "use their imagination". By lunch time, the cafeteria is ablaze with gossip, publicly shaming Winnie. Later, Kevin goes to Winnie’s house to apologize, but Winnie cannot see how to fix the unfixable. Kevin is left alone to ponder how readily he hurt the person most important to him in trying to impress those that weren’t.

Wayne begins dating Bonnie Douglas (Paula Marshall), an older woman he met at work. Over dinner, the family finds out she is 23, divorced, and has a 6 month old son named David. Norma invites them to the NORCOM family picnic and learns that Wayne is serious about their relationship, so much so, he decides to move in with Bonnie and help her take care of David. Meanwhile, still upset over Winnie not being in his life for the past few weeks, Kevin tries to get her back by buying a gift. But when he goes to her house with a huge teddy bear, Winnie has a study date with a classmate. Later, seeing them at the diner together, Kevin feels lonely and meets a new girl named Cindy, who just moved into town. He invites her to the picnic only to find out her immature behavior is due to the fact she’s only in the 7th grade and winds up giving her the big bear in his trunk. With all this stuff happening to his family, Kevin needs someone to talk to, so he turns to Winnie, who in return now seems willing to give him another chance.

With his two-nights a week Chinese food delivery job at Chong’s Restaurant, Kevin has difficulty making time to meet with Winnie, particularly as his high-strung boss, Mr. Chong (Michael Paul Chan), is always on his back. Every night had its pitfalls and perils, from scary houses and scary customers and yapping dogs, to practical jokes with Fioni’s Pizza deliveryman (delivering to a dead person at a funeral home), and having his car impounded. He also has regular customers, especially Mrs. Tambora, a lonely old lady who always wants Kevin to stay and chat. But it’s not all bad, particularly when a hippie stoner gives him a $20 tip, or when Kevin decides to re-prank the pizza guy into delivering to Mrs. Tambora. Throughout the night he often contacts Winnie by phone, but one night she breaks their date. Then his boss informs him of one last delivery to 216 Maple, which ends up being a local park, but to his surprise it was ordered by Winnie, who shows up for a late dinner date in the park.

Kevin and his friends deal with the stress of preparing for the SATs, and contemplating their futures. Unfortunately Paul is not helpful, particularly when he starts to panic and begins to focus on how the test will predetermine the rest of his life, and Kevin’s procrastination while watching Let’s Make a Deal does not help either. Meanwhile, after Jack gets a "competent" annual review at NORCOM, saying he’s ok at performing his job, he decides after 20 years, he’s had enough and seeks to leave the company. Jack talks about how an ex-NORCOM co-worker of his, Charlie, is looking to buy a furniture company, but fails to tell Norma that he wants to join the venture too. After bumping into Charlie at an ice-creamery, the truth comes out and Jack then meets with the owners of the factory and finally, with Norma’s support, seals the deal. Empowered by Jack’s example of taking a risk, Kevin sits his SATs, knowing that he won’t let his life be dictated only by the results.

December 1972 marks a time of transitions for the Arnolds. Norma graduates from Fremont Community College and Kevin has his own problems trying to get a raise from his boss, Mr. Chong so he can buy Winnie a $100 cashmere sweater. Meanwhile, the newly unemployed Jack focuses on a new future when he and his ex-Norcom friend, Charlie try to secure a bank loan to finance their own furniture factory business. However, despite it being the holiday season, Charlie gets cold feet and backs out at the last minute, deciding to return to the safety of a NORCOM salary. Jack starts to give up on his dream, but with Norma’s help, they manage to get the loan and enjoy the festive season after all. In the end, Kevin buys Winnie her sweater, but all he receives in return is the new Bread album, Baby I’m-a Want You.

Kevin’s sees Wayne evolving from the simple self-centred older brother he grew up with into a diligent and focussed family man. Wayne and his single-mother divorced girlfriend Bonnie are getting serious about their relationship, and Jack and Norma slowly warm to the idea. Wayne plans a family get together at a supper club on New Year’s Eve and he wants everyone to be there at his expense. This is much to Kevin’s dislike since he had an idea to go to a New Year’s party at a ski condo in the mountains. On the big night, the Arnolds and Winnie are there, but Wayne never shows up. Kevin learns from Bonnie that they broke up since she still has feelings for her ex-husband James, the father of her son, David. Kevin and Winnie go out searching for Wayne and eventually find him drinking beers at the laundromat. But at midnight, they watch the ball drop on TV in Times Square, marking a new beginning for them all.

When Kevin starts having car trouble, he learns that Chuck’s on-again-off-again girlfriend, Alice is the daughter of "Pistol Pete" Pedermier , the "used car cowboy", and she asks her dad to try to give him a good deal on a trade. However, when she dumps his friend for the 29th time, Kevin has second thoughts about accepting her offer. He changes his mind however, and goes with Alice to Pedermier’s Autoland to test drive a flashy red 1960 Austin Healey Sprite. While on the drive, Alice tells Kevin that she has had a crush on him ever since they first met and hugs him just as Chuck drives by and notices them. Kevin shouts out that Alice doesn’t mean anything to him, but Chuck drives off. At school, Kevin tries to explain what really happened, but Alice feeds Chuck a reversed story. Soon the school’s worst couple are back together again, but not until Chuck punches Kevin in the face. And, to make matters worse, he never did get the convertible.

In the winter of ’73, a rumor spreads through McKinley High that The Rolling Stones will play at a Joe’s Place, a dive bar an hour away out on Highway 9 . Even though Kevin doesn’t believe it, he gets talked into going by Winnie, Paul, Jeff, and Chuck. After getting a speeding ticket on Vine Street, Kevin tried to hide it from his parents, but Norma finds the ticket in the wash. Since Jack and Norma have to go square dancing with a furniture buyer, Zeke and his wife on the same night, Jack forbids Kevin to go, gesturing to him not move his car one inch off its oil spot. So Kevin, using impeccable teenage logic, takes Jack’s car instead, with the intention of "buying some milk". When they finally get to Joe’s, the parking lot is empty. After getting stopped by the police again, Winnie saves the day by making up an excuse, and they follow the trail to Wally’s Inn when they find a large crowd gathered outside, but are shooed away by the owner Wally. Then in frustration, Kevin backs up into a parked car, and the night ends in despair. He makes it back home before his parents, and is saved when Zeke accidentally hits the car. Kevin is relieved and surprised when Norma confesses she dented it too. It turns out to be a great evening, despite the fact that The Stones did go to Joe’s after all.

After chemistry class, Kevin and Winnie meet in the cafeteria and knowing Jeff is lonely, they try to set him up on a date with Ann Sheer, the new girl in school. But Jeff, whose parents have just divorced, is unable to commit be too friendly with Ann because of his attachment to Julie, the long-time girlfriend he left behind. During a friendly evening after playing miniature golf, the four go out, but Jeff leaves early when Winnie suggests they all go to the The Point. Kevin, attempting to talk about the matter, is initially annoyed by Jeff’s sarcasm and joking, but soon learns the truth, and that Saturday he asks Kevin for a ride back to his old hometown 110 miles away. Driving around his old hometown, Kevin discovers his friend didn’t want to go back home, but was frustrated about having to leave his life behind. While there, Jeff meets Julie at the diner and says goodbye to her one last time. Kevin, returning 6 hours late, still didn’t get those gutter brackets for his father, but more importantly than that, Jeff decides to unpack his room, spend time with Ann, and restart his life.

After pinning all his classmates in gym class, Kevin is invited to try out for the wrestling team by Mr. Silva, its tough no nonsense coach. Even though Wayne and Jack think he’s not committed enough to be on the team, Kevin persists when Chuck, Jeff, and Winnie push him into competing. At his first practice, the coach tests him out against the smallest and lightest team-mate, Spider, and Kevin soon realizes his gym class performance is relatively weak here. After complaining, whining, and looking for excuses, the coach himself challenges Kevin, but when he doesn’t surrender easily, he actually makes the team. Thinking he’s just going to sit on the bench, Silva makes a change, and Kevin is matched in the 140 pound weight class against the Spartans team’s Doug Gurney, whose wrestling prowess is well known. During the match, Kevin surprisingly score two points, and when Doug whispers in his ear "give up, and make it easy on yourself", he doesn’t and his shoulder never touches the mat once, getting by on his natural ability from gym class. Even though he loses 15-2 in front of his friends and father, Kevin tells the coach "Told you I was good!", earning his respect.

After Ricky asks the guys what’s wrong with him and why can’t he get a date, he finally finds a love interest with the new girl, Hayley Green and asks her to the spring dance. However her nose is big and Kevin, Jeff, and Chuck can’t help but make fun of it. In English class, their teacher Mr. Arkinson asks Hayley to read her paper on something that really bothers her about herself. Thinking to face her problem head on, she jokes how her weakness is shopping because no matter how hard she tries, nothing really matches nose but she’s accepted it because that’s who she is. Her plan backfires and the class laughs at her instead, leaving Ricky embarrassed. So he backs out by lying about having to take his cousin to the hospital for an operation on her webbed feet. At the dance, Hayley still shows up, and Kevin encourages Ricky to tell her the truth. He asks her to dance, but she came with a date, class president and captain of the football team, Brett Davis, who was moved by her speech in class. Apparently, Hayley simply knew herself and accepted who she was, unlike everyone else in school.

Kevin and his classmates take a field trip to the Nierman Planetarium to witness the total solar eclipse of March 21, 1973. On the way there, Kevin and Winnie have a fight during a Truth or Dare game when he calls her "too perfect". Chuck’s results aren’t so great with Alice either and during a pit stop, he accidentally gets locked in a rest area bathroom, and gets left behind by the bus. Winnie is so upset at being the nice girl, she throws a spitball at Mr. Plenitzer, the science teacher, who doesn’t believe it was her, so she resorts to taking a hat from the gift shop. To get even, Kevin agrees to help Louis Lanahan flush a cherry bomb down the toilet during the viewing. Meanwhile, the class bad girl, Mary Jo Genaro makes a $25 bet with her friends, Sheila and Cindy to give Harlan Abramson a hickey. On the way back, Winnie confesses she actually paid for the souvenir--she’s still Kevin’s perfect girl after all.

When Kevin and the guys get together for a Friday night of poker, each of them explains their own problems: Chuck is worried that Alice may be pregnant; Randy is concerned that he won’t be able to graduate year 11; and Jeff is accused of cheating at cards and annoys Paul with his cigar smoke. However, the real problem is Paul’s straight-laced behavior, and the guys claim they have no room for Paul in the car or cabin for their spring break ski trip. While out on a food run, they get into a fight and Paul actually says what Kevin wanted to say, that he’s "changed". But just when tensions reach a peak, their problems vanish when Randy, always the loser, finally wins a hand. Then Alice calls to tell Chuck she’s not pregnant, and Kevin and Paul understand, after 17 years of friendship, that they’re growing apart. While cleaning up, Kevin discovers Jeff’s winning streak was still intact after all--though he questions why his friend had five kings.

As the Women’s Liberation Movement gets stronger across the country in the spring of 1973, Norma doesn’t want her college degree to go to waste. She takes a full-time job as a comptroller at Micro Electronics, a start-up computer company, earning $225 per week, much to the surprise of the Arnold men. Meanwhile, Kevin is proud of his SAT’s, scoring a 1240 (650 verbal and 590 math). However, he becomes increasingly insecure when he learns that Winnie scored a 1482 (725 verbal and 757 math). She can now consider going to any of the top Ivy League universities while Kevin’s friends have to settle for Ed’s Junior College. With their fragile male egos beaten, Jack and Kevin both decide to take their women out to King Pin Lanes. Even though the men win, Norma and Winnie are good sports about it, helping Kevin realize that a more liberated world may not be so bad after all.

The Arnold clan flies to Norma’s hometown for her 25th high school reunion. Norma’s parents, Karl and Jane Gustavson (making their first and only appearance in the series) express their continued disapproval of Jack. They attempt to set Norma up with her old high school sweetheart, Roger, a medical doctor, who almost ended up together. While staying at the Gustavsons’, Norma is wooed by Roger; Jack is hurt in the sack race at the reunion picnic; Kevin is menaced by their Rottweiler; and Wayne takes inventory of the house. Kevin wonders why his father doesn’t seem to mind that Norma puts up with her parents’ meddling. Jack tells him his mother wanted more out of life than this small town had to offer, so she quickly left everyone behind. This makes Kevin finally understand his mother’s desire to break old routines.

Winnie takes a summer job as a lifeguard at a hotel resort, while Kevin considers a cross-country trip with his friends, an idea that Jack soon quashes. Frustrated, Kevin then quits his job at Jack’s factory and drives to the resort to see Winnie. Kevin then takes a job as a waiter to be near Winnie, but is then disappointed when he and Winnie are so busy they have no time for each other. Kevin gambles his gas money playing poker with the resort’s house band and manages to win big; but later, when he finds Winnie to tell her of his good fortune, he becomes shocked to see Winnie kissing a co-worker. Part one of the two-part series finale.

Kevin, furious with Winnie over her infidelity, plays another poker game, this time losing all his money and his car. He then punches the guy Winnie kissed, quits his job and hitchhikes home because he is now without a car. Winnie is fired from her job because of Kevin’s tirade; and she, too, hitches a ride back home, and Kevin happens to be picked up by the same couple. Winnie tells Kevin her side of what happened; but their argument becomes so heated that they are both dropped off at the side of the road. Soon after a thunderstorm occurs and they find refuge in an old barn where they decide they don’t want to lose their childhood relationship. The next day they make it back home just in time for the Independence Day parade, and the present-day adult Kevin reveals the fates of himself, his family, and his friends from that day onward. Part two (conclusion) of the two-part series finale.