Cory decides to make a documentary similar to The Real World for Mr. Feeny's film class. He starts filming Shawn, Jack, and Eric as they adjust to their new living situation. When Jack and Shawn get off on the wrong foot, Cory learns the boundaries between filmmaker and friend. Meanwhile, Morgan hires an actor to play Eric at home because she misses him.
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.
Jack puts girls in front of friendship when he falls for a relatively unknown girl (played by Candace Cameron). 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 Corey travel to Pittsburgh.
Shawn strictly follows a "two-week" dating rule. But Shawn begins to rethink his dating philosophy when the contents of a lost purse seem to fit his definition of the perfect girl. Eric desperately needs help studying for a test but Mr. Feeny wants Eric to go it alone. Eric hallucinates his own version of Mr. Feeny to help him.
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.
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.
Cory's senior ski trip starts off the wrong way when he sprains his ankle getting off the bus. While his friends enjoy the rest of the trip, Cory is left in the care of Lauren, an attractive lodge employee. The two hit it off and stay up all night getting to know each other.
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 for hurting her. Meanwhile, Cory must face the music when Topanga reads Lauren's letter.
Lauren travels to Philedelphia 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 citizenship class.
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.
It's prom night, and Cory & Topanga have to decide whether or not to take their relationship to the next level, as they are now "adults." Cory wants to go through with it, and Topanga says she will do whatever Cory thinks is right, but he reconsiders his judgment when he discovers that his mother is pregnant.