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.

Joy asks Boyd to double-date with Jack and her friend Anna. Boyd uses the chance to get closer to Joy. Meanwhile, Wyleen tries to have a relationship with Morgan.

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.

Wyleen gets a job working for Professor Reed. When Boyd wants to take Joy on a ride in his car, he encounters some trouble getting his car out of the impound lot. Tasha wants her overdue raise.

Wyleen gets hooked on fat-free cookies. Leonard wins free groceries and the ensuing publicity photo gets him a disciple who thinks he's the messiah. Boyd tries to follow Joy's wish that they take a break from each other.

When a new president is selected for the college, Boyd loses a job. Cookie expresses an interest in Leonard.

Wyleen develops a large cold sore on her upper lip. Boyd frets over the color of his teeth as he begins to work his new job. The crisis center is in danger of losing its funding, Boyd's first case as student liaison. Joy and Jack discuss their relationship.