Cybill's hot flashes and herbal treatments don't make her feel any younger, nor does Ira's visiting mother Ruth, who has traded in pantsuits for trendy clothes and an herbal pleasure of her own (or, as she calls it, ""a little sweet wheat""). But Ruth is a hit with Zoey, since she arrives in a pink Cadillac that's a present for her granddaughter, much to Cybill and Ira's dismay.

Cybill retaliates when her obnoxious co-star Jack mysteriously fires his friend, the executive producer, Buddy, and apologizes to Cybill for his rude - and crude - behavior. Smelling a rat, Cybill, Maryann and Cybill's producer friend Amy devise a sting operation to trick Buddy into revealing the truth behind Jack's sudden change of heart. Meanwhile, Zoey is having second thoughts about being maid of honor at the wedding of her father, Ira, and Holly after overhearing Holly remark to a friend that Zoey threw her a tacky wedding shower.

When a TV director takes his cat to see Maryann's Richard, Cybill drops by - dressed as an old woman - and becomes privy to Richard's intentions regarding Maryann.

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.

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.

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.

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.