Boyd arrives in Boston with his sister Wyleen. She is moving to Boston to attend Randolph Harrington College. Wyleen is excited at the prospect of being ""finally free from her family."" Those plans change when Boyd gets a job as a handyman at the Student Union. He has also set his sights on winning Joy's heart.
Boyd uses Leonard to try and get Jack to take an offer from Stanford, so he can get Joy to himself. Meanwhile, 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. Unfortunately he is put on the committee with Jack, who isn't fond of his ideas.
Joy introduces Boyd to her new friend Anna. Joy asks Boyd out to dinner; a double date, he with Anna and her with Jack. Boyd uses the chance to get closer to Joy. Later he finds out that he and Anna both have their own motives for double dating. Meanwhile, Wyleen tries to have a relationship with Morgan; he wants to talk.
Jack suggests that Wyleen see the school therapist to help her deal with her problems with Boyd. The therapist suggests bringing Boyd in for a session. After he relents, he discovers that Joy is also attending sessions and if you sit in the waiting room, you can hear what is going on inside. Leonard's brother is coming for visit and he isn't prepared to see him. Joy finally gets the idea that Boyd is interested in her.
Leonard confesses to having a dream about Liz and is nervous about making another date. Boyd plans a group outing for line dancing at a country bar; even Tasha is coming along. Joy tells Boyd that they need to just be friends and they (she and Jack) have already made plans for the evening. Later Joy suggests to Jack they go to the country, to which he objects. Much later in the evening, she appears at the country bar, sans Jack. Wyleen gets the opportunity to be a country singer.
Boyd is on top of the world, in his dreams anyway. It is the day after their first kiss and Joy makes some ground rules to be followed until she tells Jack. Tasha offers to manage Wyleen's singing career. Leonard is asked by the college president to sponsor a Russian student. Jack accompanies Joy to a therapy session, where he breaks down and says what is on his mind. Joy is the one thing keeping him going. That puts Joy in a quandary and Boyd on hold.
Wyleen gets a job working for Prof. Reed; she really inspires him in the writing of his new book. Boyd wants to take Joy on a ride in his car to see the fall colors; however, he encounters some trouble getting his car out of the impound lot. Tasha wants her overdue raise; instead she becomes head of the student union. Boyd uses Leonard to bid low and retrieve his car from the auction block. Meanwhile, Leonard expresses in an interest in the ""girl"" at the impound lot.
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 is trying to follow Joy's wish that they take a break from each other; instead he becomes more obsessed with her.
Boyd finds his great-grandfather's secret recipe for a great tuna fish sandwich. He starts a side-business selling the sandwiches with Tasha and Leonard's help. Wyleen has a hard time pleasing her drama teacher, however, her performance clears the house or maybe it was Leonard's fault.