The Wonder Years (season 5)

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 decide to take a tour of the small town when Kevin spots 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. The beautiful girl Kevin saw earlier, now introduced as Cara (Lisa Gerber), also shows up at the drive-in; and Kevin decides to introduce himself and have a conversation with her. For the rest of his one-week vacation, Kevin spends all his evenings with Cara, leaving his family and "Mr. Hormones" Paul (with his 25-cent condom in tow) behind, and romance develops between the two. But with the vacation coming to an end, Kevin and Cara realize that their summer romance must end as quickly as it began.

Guest-starring: Scott Menville as Wayne's new friend Dave "Wart" Wirtschafter; Lisa Gerber as Cara.

It's Kevin's first day of tenth grade at McKinley High School. Feeling alone without his best friend Paul, the day goes from bad to worse. First, Kevin meets an old bothersome fourth grade classmate, Stuart Cartesian, whose not-so-decent reminiscing turns off a would-be pretty girlfriend for Kevin. Later at lunch, Kevin finds Winnie alone, but before Kevin can make his way to the table to join her, she is surrounded by the football team. Soon after, Wayne and Wart give Kevin a "royal flush" because he accidentally stepped on the sacred 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. Kevin realizes maybe he's not so alone after all.

Guest-starring: Scott Jaeck as Kevin's government teacher Mr. Bottner.

When Kevin has a date with classmate Cindy (Heather McComb), his friends Randy and Purdle make fun of him for having his mom drive Kevin and his dates everywhere. Kevin and his friends then approach Ricky Halsenbach (Scott Nemes), the first kid in their class to turn sixteen and get his driver's license, to chauffeur them around. Kevin then breaks his date with Cindy, making up a lie that his grandmother is ill to go cruising with his friends on a Friday night; but their glorious night fades when they encounter a group of guys in a Mustang, who go around mooning people. Shortly afterwards, Kevin runs into Cindy at Zesty's Drive-in, who catches Kevin in a lie and becomes crushed. Later, Ricky is challenged by the guys in the Mustang to a drag race, but dutifully stops at a four-way stop sign. And if all that wasn't bad enough, Purdle moons Kevin's parents of all people at a traffic light, causing Kevin to flip out in extreme anger and embarrassment. As the boys decide to go home, a final insult was added to their injury as the car runs out of gas, leaving them to push the car home; but in spite of it all, 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 Sandy falls for Kevin while watching an episode of Sonny and Cher on TV, thereby beginning a secret relationship between them. Kevin feels Wayne is not the right guy for Sandy, thinking she's too smart and beautiful for him. But when Kevin notices Sandy making Wayne a better person, he backs off. Later, Kevin asks a schoolmate, Alice Pedermeir (Lindsay Sloane), to the school dance, but she already has a date. Meanwhile, Sandy prefers 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 blood is thicker than water, putting family first, and leaves Sandy to dance with another guy.

When Kevin tries out for the football team and gets cut because of his size, he discovers the new sport of soccer, where the school's misfit team welcome him. After meeting disgruntled coach Pops "The Bear" McIntyre (Paul Dooley), who is best known for his championship football days, Kevin joins the team. The players train as best they can, but Kevin soon becomes frustrated with the team's lackluster coach and their team's lack of skills. 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.

Six months after Jack and Karen's fallout (from "The House That Jack Built" in Season 4), Norma decides to try to reconcile their relationship. To celebrate Jack's 43rd birthday, the family decides to go out to dinner at Briarcliff Lodge, a restaurant of Jack's choosing, and Kevin decides to secretly surprise the family by picking up the tab with his summer job savings. However, dinner doesn't go as planned: For starters, Karen arrives separately with live-in boyfriend Michael—on his souped-up motorcycle, much to Jack's chagrin. Then the Maitre D' seats the Arnolds—and Michael—at a small table that's too cramped up for them, and Jack continues to spar with Karen over Michael. The high point of the night is when Norma presents Jack with a photo album gift, but things go downhill from there. Afterwards, however, stubborn Jack and headstrong Karen feel badly about the farce and reconcile in the end. This makes Kevin realize that what his father really needed for his birthday was his daughter's goodwill more so than gifts.

Tension arises between the Arnolds and the Pfeiffers after Alvin (Paul's father) makes a windfall gain by investing in beach front property; and a jealous Jack is irked by Alvin's spending spree: a color TV with remote, a riding mower, a swimming pool, and a country club membership. This situation also puts Kevin and Paul's friendship to the test as well, heightened when Kevin learns that Jack also could have joined the investment deal. At the country club, the "cold war" continues while Kevin and Paul are playing tennis. Kevin envisions in his mind a butler giving a stylishly-dressed Paul a tennis ball on a silver platter. The imagination sends Kevin into a fit of jealousy, which causes him to hit the ball with such force that it strays and hits Paul in the head. Back at poolside, Paul is nursing his head as Norma graciously proposes a goodwill toast celebrating the Pfeiffers' success. However, Alvin begins sobbing and tells everyone that he has actually lost everything. Back home, Kevin decides to meet Paul, apologizes about the stray tennis ball that hit Paul, and they patch things up. Paul then drops out of prep school and joins Kevin at McKinley High.

Kevin seems to be a natural at driving, except for 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. Then one day Jack has Kevin drive him downtown to run an errand so that he can stay in practice for his upcoming road test, but Kevin freezes up in fear when Jack has him parallel park in front of the store. Kevin's tension continues to build until he lies to his parents about getting his driver's license, even though they celebrate by giving him a cake and a set of spare keys to the car. Determined to secretly practice, Kevin sneaks out of bed in the middle of the night to try to use the car to parallel park; but only ends up running over the lawn mower, damaging it in the process. Jack comes out to see what's happened, and Kevin finally confesses all. In the end, Kevin gets his license with his father's help, but is subsequently grounded for a month for damaging the mower.

Guest-starring: Michael Gregory as Coach Meecham, Alicia Silverstone as Jessica

After having several recent auto accidents that led to a license suspension, Grandpa Arnold (David Huddleston) refuses to listen to his family's concerns and refrain from driving while suspended. Frustrated, Grandpa 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 his cruising days, traveling to his favorite diners and roadside attractions. For the first time, Kevin notices Grandpa's old age catching up with him; and while reminiscing about the old days and not paying attention to the road, he nearly crashes the car. Grandpa finally accepts the fact that he's getting too old to drive and sells Kevin his 1965 Oldsmobile Cutlass--for one dollar. Now Kevin will always remember his first car because it was his grandfather's last.

When Kevin's parents leave town for the weekend—and Wayne leaves the house, also—Kevin's friends talk him into letting them come over for a night of poker. 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, Alice also invites her friends, who bring or invite their siblings or friends, eventually causing things to get out of hand, and a wild party ensues. As supplies run low, Kevin and Chuck make a run to a convenience store in an attempt to purchase alcoholic beverages; but the clerk (Michael G. Hagerty) doesn't fall for Chuck's fake ID. When they return; they find total chaos, as the house is now trashed. Kevin futilely spends three hours cleaning up afterwards, but his parents return early and are shocked by what they find, and automatically blame Wayne. But Kevin is taken aback when Wayne takes the rap for the carnage—but Kevin has to wash and wax Wayne's car in exchange for getting off scot-free.

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 uncomfortable 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, Karen's friend Earth Mother delivers a cake that has written on it in decorative cake icing "Alaska or Bust." 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 ultimately 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 real world, reminding her that irrespective of where she is, they will never let her go.

Guest-starring: David Schwimmer as Michael.

As summer begins, Wayne gets a job at Jack's company NORCOM, working on the loading dock. Kevin is frustrated with missing out on a leisurely summer since his parents are pressuring him get a summer job, also. With Winnie working at a diner and Paul working as an assistant manager at a Chinese restaurant; Kevin finally takes a remedial position at the Chinese restaurant as well. One day, while cleaning his room, Kevin finds a card from Cara, his summer fling from last year; and on the way to work with Paul the next day, Kevin spontaneously decides to go back to the lake with hopes of reuniting with Cara. But Cara isn't thrilled to see Kevin and wonders why he came, since he never replied to her Christmas card. Cara then leaves, and the next day (the boys having spent the night in the car) tells Kevin that she now has a boyfriend. Kevin then wonders why he ever tried to get back together with Cara in the first place, when he still has Winnie.

When a jealous Winnie thinks Kevin had gotten a little too friendly with a waitress (Sarah Dammann) at Fatso's drive-in, she berates Kevin and abandons him at the table and joins 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 other girls he knew in his past (through clips from past episodes). Although his friends and Wayne try to help him out, it's no use, and Kevin 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.

Recurring guests: Scott Nemes as Ricky Halsenbach, Andy Berman as Chuck Coleman, Michael Tricario as Randy Mitchell