Eric moves back home and Cory promises to find him a place to stay. Things take a strange turn when Eric's new roommate turns out to be Shawn's half brother Jack.

Cory turns the camera on Eric, Shawn, and Jack to make a film about them, but soon a fight between Shawn and Jack erupts and Topanga wants Cory to intervene.

Shawn has a hard time with the news that Cory applied to Stanford, a school Shawn could never get into. Shawn starts to suspect he and Cory are going to grow apart and decides to end their friendship sooner rather than later.

Eric decides to start his own fraternity (Magnum P.I.); Shawn begins to slack off on school work because he doesn't expect to get into college.

Jack puts girls in front of friendship when he falls for a girl named Millie. Eric, on the other hand, soon discovers that the girl is a witch but Jack is in too deep to see the truth. This puts the two at odds. Meanwhile, Topanga overcomes her fear of flying when she and Cory travel to Pittsburgh.

Salem the Cat uses a time ball to transport Cory back to the 1940s. Cory is shipped off to fight in World War II and must leave Topanga behind.

Shawn is forced to reconsider his own stubborn determination to keep relationships brief when he believes that he might have found a suitable match.

Cory tells Shawn about the lost purse mix-up and Shawn realizes he might be in love with Angela. However, Angela might not feel the same way. Across town, Jack and Eric are nervous about hosting Thanksgiving dinner for the Matthews family in their new apartment.

Cory becomes jealous when Shawn outperforms him in a work-study job. Eric feels self-conscious when Amy enrolls in his creative writing class.

The girls want to go dancing but Shawn and Cory aren't in the mood. The ladies go out on the town with two handsome co-workers. Shawn and Cory fight their jealousies and try to figure out how to make their girlfriends happy.

Topanga spends her first Christmas at the Matthews home. Cory is happy at first but when traditions clash, he starts to have misgivings about their future together.

Alan is forced to re-evaluate himself as a father when he notices that his relationship with both his sons is lacking.

Shawn tries to win tickets to the super bowl.

While on the senior class's ski trip, Cory sprains his ankle and meets another woman who takes care of him and chases him to stray from Topanga.

On Valentine's Day, Shawn's ex-girlfriends are so certain he is going to ruin his relationship with Angela that they kidnap him in order to keep him from hurting her. Meanwhile, Cory must face the music when Topanga reads Lauren's letter.

Lauren travels to Philadelphia to see Cory, and Topanga tells Cory to go out with her to test his feelings. Despite Shawn's warnings that it's a trap, Cory agrees to go out with Lauren. Eric proctors for Feeny's citizenship class.

The gang finds themselves locked in the school, all alone, during detention.

In an effort to numb his heartache, Cory steals a bottle of whiskey from Alan. He offers to share the bottle with Shawn and the two drown their sorrows. Trouble arises when Shawn discovers he likes the alcohol a little too much.

A Hollywood director spots Eric in a school play and asks him to be in his show. Shawn and Jack get the chickenpox and Topanga takes care of them.

When Topanga goes to an art exhibit with Angela, she meets a charming guy and threatens to break-up Cory and Topanga forever.

Cory and Topanga are back together but decide to keep it a secret from Shawn. They pretend to still be arguing to make Shawn think he is the one who reunited them.

On prom night Cory and Shawn decide they are ready to become men and while Angela is not ready, Topanga agrees to getting a hotel room.

Cory has problems accepting all the changes that are happening around him.

The group is getting ready to graduate and Mr. Feeny assigns them one last assignment about what they are feeling the last few weeks of school before graduation.