Boyd arrives in Boston with his sister Wyleen. While she is attending Randolph Harrington College, he gets a job as a handyman at the Student Union.

Boyd uses Leonard to get Jack to take an offer from Stanford, so he can have Joy to himself. Wyleen finds another student who's also having trouble adjusting to college life.

Wyleen is the subject of a student film, showing her daily life. When Jack doesn't seem to want to make the effort, Boyd takes the challenge of raising the funds to keep the school's non-essential programs alive, including Joy's storytelling program.

Boyd plans a group outing for line dancing at a country bar. Wyleen gets the opportunity to be a country singer. Leonard confesses to having a dream about Liz and is nervous about making another date.

Joy wants to break up with Jack after kissing Boyd. Tasha offers to manage Wyleen's singing career. Leonard is asked by the college president to sponsor a Russian student.

Everybody wants to have lunch with Boyd so they can get his advice. Wyleen wants to him to be there when she has lunch with the newly reformed Cookie. Joy wants advice about her pending wedding to Jack. Tasha wants assistance with her husband Darrell. Leonard worries about talking about radio in front of Jack's students.

Joy's mother comes for a visit and takes more of a liking to Boyd than is comfortable for him. Leonard needs an insurance physical and gets an appointment with Tasha's gynecologist. Wyleen is also going there because she is thinking about making the next step in her relationship with Drake.

Cross gets on Tasha for disciplining the son of a major college benefactor. Wyleen tells Boyd it is time for him to move out. He looks for a place to stay and winds up with Tasha. Joy is hired by Cross as a professor in Jack's department.