Maryann goes home to Buffalo for an uneasy reunion with her parents , and to attend a 25-year reunion of her high-school classmates - who treated her like dirt. When Maryann can't make her high school reunion, Cybill decides to pose as Maryann and go in her place. Cybill had convinced Maryann to attend her high school reunion and planned to accompany her, but when the pair returns to Maryann's home town of Buffalo, N.Y. to take on the former classmates who made Maryann's life intolerable, Maryann learns that her son - who she believed was traveling with Greenpeace - is actually living with her parents. When Maryann consequently opts to forgo the reunion to spend time with him, Cybill, not one to miss an opportunity, goes to the reunion as Maryann in order to claim sweet revenge on the classmates who made Maryann's high school experience a nightmare. Meantime, Cybill is also spearheading efforts to make Thanksgiving dinner plans.

Maryann is acting more bizarre than usual during a Valentine's Day outing with Richard and her visiting son. Meanwhile, Zoey moves in with Ira to spite her mother. Sparks fly between Zoey and Maryann's son, Justin. Maryann arranges a Valentine's Day dinner with her son and her new flame but panics and shows up on Cybill's doorstep with Justin and her beau, looking for moral support - just as Zoey is leaving to meet Ira. When Zoey and Justin see each other again - after years apart - they begin spending time together, and, although Maryann loves Zoey like a daughter, she fears that Zoey may break her son's heart. Meanwhile, Cybill spends Valentine's Day with the special guy in her life - her grandson, William.

Cybill puts her foot down when she's chosen as a model for a shoe campaign only to see a billboard with her face - on a younger, thinner woman's ""waif"" body. Cybill decides to defend women of all shapes and sizes by defacing a billboard that depicts her face with someone else's waif-like figure. Meanwhile, Maryann freaks when she discovers that her son, Justin, is two-timing Zoey, and Ira decides to give up caffeine, which creates some abnormal side effects.

Learning that her film's a flop, Cybill has nothing to throw in the faces of her friends when she attends a neighbor's wedding. But that's not the case for Zoey, who accidentally decks the bride while dancing.

Cybill doesn't realize that her mom, who's visiting for Mother's Day, is within earshot when she says she's worked her entire life trying not to become her mother.

With Cybill as the organizer, Maryann's bachelorette party turns out to be one last evening stalking Dr. Dick. Realizing their stalking days are almost behind them, Cybill and Maryann agree that one last act of torment is in order. Zoey and Rachel join the duo in a rented van, equipped with the latest in surveillance technology, staking out Dr. Dick's house. Their mission: to inject Dr. Dick's water supply with a barrel of liposuctioned fat stolen from his office. But mid-execution, Cybill and Maryann overhear ""Mrs. Dr. Dick"" Andrea tell Dr. Dick that she's leaving him, causing Maryann to rethink her own marriage plans.

The series begins its fourth season with a trip back in time to the 16th century, as Cybill undergoes past-life regression treatment on the advice of her therapist when she begins having erotic dreams about Maryann's jilted beau Richard. She discovers that Maryann's poor choice in men goes back to the days of Henry VIII, when Maryann was Anne Bolyne, and returns to the present just in time to head off a close encounter between Maryann and the despised Dr. Dick. Joining Cybill in the Court of King Henry VIII are Zoey as Ariel's father, Ira as her brother the poet, and Justin as a serving wench.

Zoey rejects Cybill's advice about what to wear for her first piano competition, and Cybill mourns the loss of a mother-daughter moment. After having been brushed off by Zoey, Cybill meets a young girl who welcomes her mothering - and her father isn't bad either. But when he turns out to be a cad, Cybill and Maryann scheme to get revenge. In the meantime, Ira and Justin battle over whose good luck charm Zoey should wear for her competition.

When Rachel goes into labor and Maryann has an appendicitis attack on the same day, Cybill finds herself stretched thin trying to care for each of them. After convincing a panicked Rachel that having a second child is a piece of cake, Cybill must reassure Maryann, who is delusional from pain-killing drugs, that her hallucinated dinner party is a smashing success.

Maryann's son Justin decides to move to San Francisco for a new job, and Cybill convinces a reluctant Maryann to see a therapist and confront her irrational fear of losing her son. Cybill's suggestion backfires when Justin brings Maryann's ex-boyfriend, Richard, to the group therapy and the session descends into chaos. Meanwhile, Cybill quits an acting job out of disgust with Hollywood's lack of respect for older women.