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.

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.

Boyd starts a side-business selling Tuna sandwiches with Tasha and Leonard's help. Wyleen has a hard time pleasing her drama teacher.

Wyleen discovers a there is a secret woman's society on campus and decides she needs to join them. Butterfield schedules to meet with Leonard about something.

Tasha detects that Joy might be a bit jealous of Boyd. Wyleen learns about conspiracy theories and hidden agendas from Professor Reed. Leonard gives up his job at the cafeteria to go on unemployment and spend his time in the park, where he makes new friends.

Tasha suggests to Jack that he recruit Boyd to organize a surprise party for Joy's birthday, a date he'd forgotten. President Butterfield tries to inform Leonard that his funding has been cut.

Tasha sets Boyd up on a blind date. Joy accidentally calls Jack "Boyd". Leonard helps Tasha move into her newly painted office. Wyleen, still working for Professor Reed, must listen to him deal with losing Joy.

Wyleen decides to run for president of the freshman class.

Boyd searches for the name of the landlord of their building, since the heat has been off for the past two days. The college entertains an obnoxious alumnus, who is funding the establishment of a new media center.

Boyd and Wyleen host the Pritchett family barbecue. Joy seems to get very tired, every time her pending wedding to Jack is mentioned. Leonard has a part-time job delivering meals to shut-ins and his first stop won't let him go. Wyleen is struck on the head by a flying pork chop that brings them to the hospital.

Wyleen and Boyd decide to hold a get-together for Thanksgiving. Wyleen invites Cookie in hopes of getting a part in the spring play. Jack and Joy try to spend their holiday working at a homeless shelter that is filled mostly with yuppie volunteers.

Boyd struggles to pay Wyleen's tuition for next semester. To raise funds, he gets a part time job working as a janitor. Leonard and Wyleen also take janitorial positions. Jack learns about the finer points of the student body and relationships from Professor Weaver.

Leonard is traveling home to his mother's for the holidays and his joke about a bomb at airport security gets him and Wyleen held for questioning. Tasha performance review is coming up. Jack would like Joy to take her art work a little more seriously.

Trying to study for her finals, Wyleen is fighting a cold, Boyd's interruptions and Jack's cryptic messages about the content of the final. Boyd cons the campus radio station manager into letting them use the station equipment. Instead of cutting a tape, Boyd lets Leonard rave out over the air about the blues he's feeling.

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.

Boyd and Jack discover a pair of shoes that might have once belonged to JFK. After displaying their lack of knowledge, Tasha tells Boyd they should try to get some culture. Everyone else is imagining what they can do with the money from the sale of the shoes.

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.