Kevin enters uncharted waters when he meets an older girl during his summer vacation.
Guest Stars:
Holly Sampson, Juliette Lewis, Jodie Rae, Noah Kaplan
Kevin has trouble in math class when he comes up against a teacher who Kevin thinks is completely unreasonable.
Guest Stars:
Robert Picardo, Steven Gilborn, Francia DiMase, Joie Magidow, Sierra Samuel
Kevin wants to get to the mall to see a girl he can't stop thinking about, but the only way he can is by begging his brother to drive.
Guest Stars:
Juliette Lewis, Jennifer Baron, Elyse Eberstein
Kevin thinks his mother is being over-protective when she tries to stop him from playing tackle football after school.
Guest Stars:
Ben Stein, Juliette Lewis, Michael Tricario, Brandon Crane, Sean Baca
Kevin, Paul and Winnie become involved in a production of "Our Town." Trouble begins when Winnie gets stage fright. Kevin thinks he's set because all he has to do is operate the spotlight.
Guest Stars:
Ryan Francis, H. Richard Greene, Lynn Milgrim, Sean Baca, Joe El Rady
When Kevin and Paul get on each other's nerves, they try to become best friends with two other boys.
Guest Stars:
Marty Belafsky, Brandon Crane, Dianne Hull
When the Arnold family car breaks down and Jack can't fix it, Kevin hopes his father will buy something more fancy.
Guest Stars:
Jodie Rae, Noah Kaplan, Sean Baca, Patrick Cronin, Biff Yeager
Kevin is looking forward to the visit of an old family friend, Gina, until he discovers his first pimple.
Guest Stars:
Ben Stein, Heather Green, Patricia Nickell, Tony Nittoli
Kevin decides cheating is the only way to get ahead in math class.
Guest Stars:
Chris Demetral, Robert Picardo, Steven Gilborn, Eric Ratican
Kevin joins a band, The Electric Shoes, when he is inspired by The Beatles appearing on the Ed Sullivan show.
Guest Stars:
Joshua John Miller, Raye Birk, Jodie Rae, Ben Slack, Sean Baca
Kevin wants to take Susan Fisher to the dance, but she has a boyfriend, Donald Wallach. However, he hears rumors that they have broken up, so he's about to ask her until Donald interferes. Linda Sloan, his lab partner, suggests that they go as friends so they do. They have a good time in the beginning, but it turns sour when while Linda is dancing with Steve Padway, Kevin dances with Susan and they have punch. How is it bad? Susan leaves and Linda comes back and asks if they half-filled cup of punch that Susan left is for her, but Kevin says that it's Susan's in a not-so-nice sort of way. That basically breaks Linda's heart and she leaves. Kevin is about to ask Susan to dance again but she's dancing with Donald, so Kevin leaves, not knowing that Winnie came in, probably looking for him.
Guest Stars:
Maia Brewton, Ben Stein, Kelly Packard, Krista Murphy, Sean Wohland
Trouble begins in the Arnold household when Grandpa Arnold arrives and gives Kevin a dog - a responsibility Jack doesn't think Kevin can handle.
Guest Stars:
Gary Grossman, David Huddleston, Jodie Rae
When Carla breaks up with Paul, Kevin sets him up with Winnie to make Carla jealous. But when Paul starts having feelings for Winnie, the friendship is put to the test. To Be Continued...
Guest Stars:
Robert Picardo, Juliette Lewis, Krista Murphy
To make up for being rude and insenstive to Winnie, Kevin makes her a Valentine's card, but it is accidently placed in Becky Slater's locker. When Becky finds the card, she thinks Kevin wants her back - setting the two up for a showdown.
Guest Stars:
Ben Savage, Wendel Meldrum, Crystal McKellar, Krista Murphy, Sean Baca
When Kevin and his dad build a treehouse in the backyard, they discover they get a good view of an attractive neighbor planting her tomatoes. Meanwhile, Doug is in shock after having heard "the talk" from his dad.
Guest Stars:
Brandon Crane, Sean Baca, Janet Wood
A new student teacher tries to make something of the 8th-grade boys' Glee Club, but without much success.
Guest Stars:
Troy Slaten, Dustin Diamond, William Lanteau, Michael Tricario, Brandon Crane
Pressure is brought to bear on Kevin and Winnie's relationship when they are invited to a notorious make-out party.
Guest Stars:
Ben Stein, Crystal McKellar, Krista Murphy, Suzy Broad, H. Richard Greene
It's tax time and Jack is in a bad mood. Meanwhile, Norma worries about the Apollo 13 astronauts and Kevin worries about his class assignment - to write his own obituary.
Guest Stars:
Michael Bower, Emily Schulman, Salome Jens, Yunoka Doyle, Troy Searcy
When Kevin keeps making the cut for the school baseball team, he worries about whether it is because of his talent or because his dad saved the Coach's life in Korea.
Guest Stars:
Harrison Page
When Kevin thinks the best he can do in math is a B, his teacher Mr. Collins sets him the task of getting an A and even offers him private lessons. When Mr. Collins suddenly pulls out of the lessons shortly before the exams, Kevin feels betrayed and fills his exam with nonsensical answers.
Guest Stars:
Steven Gilborn, Raye Birk, Sean Baca, Phyllis Flax
When Paul is voted "brainiest" in Lisa Berlini's latest poll, he goes through a crisis but is helped through it by Mrs. Arnold - who he also develops a crush on.
Guest Stars:
Michael Tricario, Brandon Crane, Sean Baca, Joshua Waggoner
Kevin isn't sure whose side to take when Karen decides to enroll in a liberal college and Jack is dead-set against it.
When Jack begins to complain about dry rot in the house, Kevin begins to think that his father might consider moving. When it is revealed that the Arnolds are staying put and it is the Coopers who are moving out, Kevin buys Winnie a ring as "insurance." Kevin decides to attend Karen's graduation from high school rather than watch Winnie leave.
Guest Stars:
Ben Stein, Crystal McKellar, Krista Murphy, H. Richard Greene, Lynn Milgrim