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.

Cybill and Maryann masquerade as ladies of the night to foil an evil prank by the dastardly Dr. Dick. The scheme conceived by Dr. Dick goes wrong when his hired thugs mistakenly drug Cybill instead of Maryann and deposit her in a seedy bus station in the middle of nowhere. To make matters worse, when Maryann comes to rescue Cybill, her car gets stolen and both women end up stranded. The two friends finally get a ride home when two unsuspecting high school boys looking for a good time mistake them for ladies of the night. Meanwhile, Ira tries to instill in Zoey a love for basketball when he gets her a job playing the organ at a Lakers' game.

In a fit of romantic nostalgia, Cybill writes a letter to her first love, Bobby Ray, and is pleasantly surprised when he flies in from Memphis to take her out on a date. After spending a wonderfully romantic evening with Bobby Ray, Cybill's faith in love is restored - until she realizes that his criminal history extends beyond being just a thief of hearts. Meanwhile, when Zoey's first love, Gianni, visits from Italy, she worries that seeing him will destroy the magic of their short-lived but passionate romance.

Following her mother's untimely passing, Cybill finds what appears to be a love letter to an unknown man in Bakersfield. She is shocked that her supposedly conservative mother may have had a longstanding, passionate secret love affair. Curious about this hidden part of her mother's past, Cybill travels to Bakersfield with Maryann and Zoey to deliver the letter to the mystery man herself.

When Cybill's garage roof collapses and requires expensive repairs, she tries to get a loan from the bank, only to discover that the loan officer turns out to be her disgruntled former fan, Minnie Arbogast. Adding to Cybill's troubles, Ira accuses Maryann of causing the breakup of his marriage to Cybill. After trying unsuccessfully to reconcile her two friends and resolve her own financial crisis, Cybill gets help from an unlikely source - her former enemy and new-found friend, Minnie.

It's the year 2027, and Cybill and Maryann, now senior citizens, are still sipping martinis and insulting men. When they come across Cybill's diary from 97, Cybill begins to read aloud from the book, and one of the passages hurts Maryann's feelings - creating a rift between the two friends. Cybill and Maryann must travel 30 years into the past to resolve the issue and discover that their friendship has withstood the test of time for good reason.

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.

When obsessed fan Minnie steals Cybill's wax head from Madame Tussaud's, the museum simply replaces it with the head of another blonde actress. Cybill and Maryann are outraged, so they concoct a scheme to travel to London and return the real ""Cybill-head."" Meanwhile, Zoey decides to give up her career as a pianist for an office job, while Cybill and Ira try to save her from a life of corporate drudgery.

Cybill gets a job as a spokeswoman on a cruise ship, but when she and Maryann take a cruise, it turns out to be one of displeasure: Dr. Dick, relentless in his efforts to win back Maryann, puts Cybill in a difficult situation by giving her a letter for his ex that Cybill knows will make Maryann ""melt down.""

Cybill hosts a Halloween eve telethon, and recruits Maryann, Zoey, and Ira to help out. Things go fine at first, until Cybill and Maryann begin to air their differences on the air!

Cybill endures her new role as a sitcom mom, even though she thinks it could mean the end of her career, until her life is shaken up when a 4.0 earthquake rattles the city and inspires her to quit and ""follow her bliss."" Next thing she knows, Maryann convinces her that they should go to a ""schmoozing"" where Cybill meets a prominent female playwright. Meanwhile, Rachel shares some shocking news of her own with the family.

Cybill throws herself into her role when she is cast to play the mother of a sweet teenage girl on a network sitcom. In reality, the girl turns out to be a tough-talking, ultra-hip teen, but Cybill is determined to mentor the difficult youth. The pending birth of Rachel's baby has everyone wondering who will be the godmother, and Maryann is hurt when no one even considers her as a possible choice.

The family take cover when Cybill's hormones rage after she opts to cope with menopause the ""natural way"" rather than with prescription durgs, while her visiting mother creates her own waves in the house and Ira tries to light a fire with Zoey's teacher Julia.

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.

Maryann is shocked when Cybill tells her she had an affair with a married man - and now wants to rekindle the romance. Maryann reels from Cybill's hypocrisy, since Cybill is always advising her not to even consider going back to the cheating Dr. Dick. But Cybill, head-over-heels in lust with Roger, refuses to admit to her own double standard. Meanwhile, Ira is hurt when he overhears Cybill wonder about what might have been if she had never become Mrs. Woodbine

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.