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.
Wyleen discovers a there is a secret woman's society on campus. She decides she needs to join them. Butterfield schedules to meet with Leonard about something; instead he begins to spills his guts about a relationship with his secretary and personal life. Boyd discovers that Joy is a member and asks her to help Wyleen get in; however, she advises against it. Joy begins to think she might be a snob based on Boyd's reaction to her recommendation. Boyd concocts a plan to get her in that almost works; instead she joins another club.
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 tells Boyd about Joy's touch of jealousy, especially after Joy meets Wyleen's friend who's staying at their apartment. They put together a plan to make her more jealous, but everything goes too far, until the truths are revealed.
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. Eventually Jack and Boyd come to an agreement when Boyd determines that she really wants a party. A plumber comes to fix the sink and Wyleen gets a handle on the subject for her paper. The plumber also had Professor Reed for communications. Leonard packs up his personal thing and then starts packing up the shoes. Joy returns some books to him and finds out about the firing. She offers him a drink of wine from one of the bottles she was taking home. Two bottles of wine later and they are trying on antique shoes and having a great time. Meanwhile, everybody is at the apartment awaiting Joy's return. It's obvious that neither Jack or Boyd thought to make sure that Joy came home at the right time.
Tasha sets Boyd up on a blind date. Joy makes a Freudian slip and calls Jack, Boyd. It is obvious she has some feelings for Boyd. Leonard helps Tasha move into her newly painted office, but the paint makes the door stick and they become trapped in the office. Wyleen, still working for Professor Reed, must listen to him deal with losing Joy. Boyd nervously makes a phone call to his blind date when Joy comes over to ""talk about us."" They try talking but get nowhere and finally decide she needs they need to be apart. Jack proposes to Joy and she accepts. Leonard and Tasha make a pact to get together if there still both alone when they reach 40
Wyleen decides to run for president of the freshman class. She needs a full time employee of the college to sponsor her. Brenda doesn't seem to be doing the job and Wyleen's opponent is sponsored by Jack. Those two facts and despite his political past, Boyd decides to run her campaign. James Carville, a noted campaign manager, offers Boyd some advice. Boyd and Jack make their protégés campaigns a place to attack each other. Wyleen, more worried about her mid-term, forgets to vote and that has an impact on the final outcome.
Boyd searches for the name of the landlord of their building, since the heat has been off for the past two days. Meanwhile, the college entertains an obnoxious alumnist. She is the benefactor who is funding the establishment of a new media center. When it is discovered the new center is slated to be put in their apartment building; Boyd and Wyleen find out the reason and with Leonard's help, right the wrong.
The Pritchett families barbecue, normally held in August in Virginia, is being held in Boston in November. 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. Tasha meets the ""Dr. Feelgood"" of her dreams. Joy passes out and is brought to the hospital. Leonard brings his shut-in to the hospital. After everyone is attended to, the barbecue can continue.
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 and ""need a descriptive word"" priest. Boyd and Wyleen go in search of a fresh turkey and bring one home. Jack and Joy join the celebration and her cranberry sauce kills the turkey.
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. The job takes away from Wyleen's study time and while cleaning her classroom, she discovers the answers to Jack's mid-term and realizes how much she doesn't know. Wyleen talks to Jack about cheating and he mis-interprets her. Boyd gets the dirt on Mrs. Taggert and works out an arrangement to pay the final $200 of Wyleen's tuition.
Leonard is traveling home to his mother's for the holidays. Tasha asks Boyd to straighten up; her performance review is coming up. Leonard's joke about a bomb at airport security gets him and Wyleen held for questioning. Jack would like Joy to take her art work a little more seriously.
Wyleen is trying to study for her finals. She is fighting a cold, Boyd's interruptions and Jack's cryptic messages about the content of the final. Boyd uses the presence of Tasha to con the campus radio station manager into letting them use the station equipment to cut a demo tape with Leonard. Instead of cutting a tape, Boyd lets Leonard rave out over the air about the blues he's feeling. Wyleen makes quick work of Jack's exam and Leonard begins a new career.
Boyd, Slinky obsessed, becomes the one everybody wants to have lunch with so they can get advice and/or assistance. 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 who's just come back into town, she wants a divorce, but is afraid he'll sweet talk her out of it again. Meanwhile, Leonard worries about talking about radio in front of Jack's students. So they arrange to go to lunch at the same place where Boyd has his three lunch dates. Turkey burgers for everyone!
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. Is culture ready for them? Evidentially not. They encounter a couple of rough art admirers, whom they get into a fight with. That Tasha resolves, emasculating Boyd. Meanwhile, everyone else is imagining what they can do with the money they are going to make from the sale of the shoes and who is going to keep the shoes until the Sotheby's office opens.
A new president is selected for the college and plans to make some sweeping changes; one includes the elimination of Boyd, when they don't see eye to eye. Cookie expresses an interest in Leonard; she charges Joy with setting up the date. Leonard takes a ""Courtney Love strength tranquilizer"" before his date with Cookie. Later Cookie makes an observation on Joy and Jack's relationship, that gets them talking. A now unemployed, Boyd is overwhelmingly nominated student liaison.
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. While doing research at the crisis center, Boyd takes phone calls, including one from Joy. Jack finds out about his book, his relationship and his hairline.
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 and Boyd and Tasha's disagreement about their need for office space.
The college is going to open a new theater. Wyleen gets the lead in the play ""The Tea Ceremony""; however, there is a protest about her playing a role that would be better for an Asian. Joy arranges a date for Tasha and also tries to fix her hair. The date turns out to be Kareem Abdul-Jabbar. Jack searches for an editor for his new book. Leonard reluctantly agrees to the task but becomes a replacement for Joy.
Joy's mother comes for a visit and takes an instant liking to Boyd; more of a liking 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. Tasha later finds out that Drake has other action on the side; she lets Boyd know about it.
Boyd and others are against a tuition increase proposed by Cross. Wyleen wants to borrow money to obtain a fake ID. When the guy who makes the fakes is caught, Cross uses the fact that Wyleen had an ID made to try and sway Boyd's vote. Leonard's guest for his radio show is Tasha's estranged grandfather. Cross pursues his interest in Joy.
A men's magazine want to do a layout featuring the women of Harrington. Boyd is for it, Tasha and Wyleen are against it. Tasha changes her mind when she sees the photographer. Wyleen changes her mind when she is told she has the right kind of attitude and could make $5000 for posing. You can guess why Boyd changes his mind. Meanwhile, Leonard gets a date with a former centerfold and Cross takes Joy out to dinner at the same time Jack takes the editor of the men's magazine.
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. Leonard's dog loves his carpet, so he tries giving him to Tasha. Boyd delivers a briefcase to Cross's home and meets his undereducated Cockney ex-wife. Cross wants him to help keep it a secret from the television people. Wyleen's first day as a waitress is a nightmare.
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. Cross wants Boyd to get Tasha to show a marked improvement in behavior towards the students. Wyleen tries living on her own as Tasha tries to be nice. Leonard tries to ask Cookie to marry him.