Boston Common

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.

At Jack's suggestion, Wyleen see the school therapist to help with her problems with Boyd. The therapist suggests bringing Boyd in for a session. Leonard's brother is coming for visit and he isn't prepared to see him.

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.