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.

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

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.

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.

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.

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 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 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.""

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.

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 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.

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.

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.

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.

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 forgot Ira's birthday and, to ease her guilty conscience, then concocts a crazy scheme to kidnap him and surprise him with the perfect gift - courtside tickets for a Lakers game. Maryann and Zoey act as Cybill's accomplices in the kidnapping scheme and successfully complete their mission - only to discover that they've abducted the wrong man. Meanwhile, Cybill's long-lost niece, Claire, visits from Bakersfield and is starstruck with her aunt's glamorous Hollywood. While Cybill entertains Claire, she finds a photo showing her with her brother, a man she never knew - and can't remember.

Jeff convinces Cybill to pretend they're still married to please his sweet but old-fashioned grandmother. While Jeff and Cybill are celebrating their pretend 25th anniversary with grandma, the waiter, who is nervous about telling his parents that he's gay, introduces Cybill as his fiancee. Meanwhile, Maryann and Richard enjoy a romantic vacation in the country until the trip gets sidetracked by a veterinary emergency and Maryann finds herself delivering a calf.

Maryann convinces a reluctant Cybill to go on the blind date with Bruce, who turns out to be an offensive jerk. Although Cybill is repulsed by Bruce's piggish behavior, after a storm straps him at Cybill's for the night along with Maryann, Zoey, Ira and his mother, she is determined to be nice to him after he saves the life of Ira's mother. Meanwhile, Maryann and Dick work on their co-dependency issues, and Ira tries to improve his relationship with his mother.

Cybill and Maryann each get a shock when Cybill discovers that she's allergic to chocolate and Maryann gets a surprise visit from her parents, who are in town for a bowling tournament.

Cybill's Daddy, who failed to show up for Christmas, breezes into town with news that he has gotten Cybill a plum spot on a TV show about Southern women who have made it big. But it's just another disappointment for Cybill when she realizes he has done it to promote his failing car dealership.

When Zoey's first love, Gianni, visits from Italy and steals her heart with his good looks, charm and romantic gestures, Cybill suspects he will soon propose marriage. Unfortunately, the seemingly perfect Italian turns out be a cad who makes a secret pass at Cybill behind Zoey's back. After rejecting the overly-amorous suitor, Cybill must decide whether or not to break her daughter's heart and tell her the truth. Meanwhile, Maryann is bent on wreaking cruel revenge on the lecherous Gianni.

Cybill is thrilled when she gets a job hosting a popular morning talk show - until she discovers that her co-host is a prissy, jealous domestic goddess-type who enjoys playing live, on-air practical jokes on Cybill. Adding to her troubles, Cybill finds herself both sexually attracted to and morally repulsed by her deceitful new producer. Meanwhile, Ira stands in as Cybill's best friend and advisor while Maryann goes on a shopping spree in Paris.

Cybill's show with Julie is being plugged; Dr. Dick steals Maryanne's money; Cybill and Maryanne are arrested for murder when Dr. Dick's boat explodes. This ""to be continued"" cliffhanger episode ends up being the series finale.