As the Keatons try to persuade Steven that he needs a relaxing hobby, Jennifer nervously awaits the arrival of her new friend, Josh Wakefield, who has agreed to work with her on a project for the French Club. When Mallory realizes that Josh is the younger brother of Jeff Wakefield, her former high school boyfriend, she becomes overprotective and reminds Jennifer how Jeff jilted her when he went to college. Mallory just assumes that Josh will do the same to Jennifer.
Mallory's distrust of Josh increases when she learns that he intends to attend Jeff's alma mater, Princeton. After sharing her misgivings with Elyse and learning that Josh has asked Jennifer to the prom, Mallory decides she must confront her sister. Jennifer, who is very excited about her new relationship, resents Mallory's assumptions about Josh and the sisters begin to argue. Finally, Nick suggests to Mallory that they go out with the couple so she can get to know Josh better.
Unfortunately, the dinner is a disaster. Mallory grills Josh about his intentions and Josh. Put off by Mallory's questions, he leaves the restaurant with Jennifer following closely behind. Back at home, Mallory calms down and apologizes to Jennifer, realizing that she must live her own life and make her own mistakes.