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

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.

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.

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.

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.

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 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.

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.

Cross is going to be featured on a public television program called American Mind as a prominent educator. Boyd is tired of paying for everything and wants Wyleen to get a job.

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.

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.

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.

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.

Boyd and others are against a tuition increase proposed by Cross. Wyleen wants to borrow money to obtain a fake ID. Leonard's guest for his radio show is Tasha's estranged grandfather.

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.

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.

The college rolls out a new credit card program that it locates in the student union. Wyleen's been approved and begins to spend and spend. Leonard is caught in the middle of Jack and Joy's separation as well as Boyd and Tasha's disagreement about their need for office space.

Wyleen gets the lead in the play The Tea Ceremony. Joy arranges a date for Tasha and also tries to fix her hair. Leonard reluctantly agrees to become the editor for Jack's new book, but becomes a replacement for Joy.

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.

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.

Wyleen decides to run for president of the freshman class.