Maryann introduces Cybill to her new boyfriend Bob, a bassoonist with the philharmonic. Cybill is lost without her best friend and feels hurt when Maryann starts blowing her off to be with Bob all the time.

A rotten experience in the Big Apple in 1969 took a chunk out of Cybill's self-esteem, so, for her birthday, Maryann, Rachel and Zoey take her to New York and teach her how to bite back.

Maryann insists that it's no coincidence that Cybill's luck improved when Zoey moved out, especially after a psychic senses a "negative energy" in the house.

To land a role as a cop, Cybill prepares by riding with an officer on duty. But when his wife goes into labor, Cybill is left with the car, the siren and a call from Maryann in trouble.

Ira brings his new girlfriend to Zoey's sweet sixteen birthday party and Cybill and Maryann both like her until they discover she has uncontrollable multiple personalities. Meanwhile, Zoey and Sean, a busboy from the restaurant, are smitten with each other.

Cybill is attracted to a guy she meets, while they walk their respective dogs, who turns out to be Ira's ex-psychiatrist. Meanwhile, Maryann befriends her ex-husband's new girlfriend Sharon in her continuing scheme for revenge.

When Cybill was sixteen she wrote a letter as an assignment for English class about her hopes and dreams for the future. Thirty years later, her former teacher has mailed it to her. Cybill's afraid to open it because she thinks it'll be too depressing.

Ira tells Cybill that his book "Lowenstein's Lament" is being made into a movie and that she's a shoe-in for the lead.

Cybill has a date with movie star Dennis Oliver only to be lost in his shadow after the Oscars. He drops her off and asks to use her bathroom: she thinks he's trying to pull a fast one and is surprised when he excuses himself without even asking her for a night cap. He's arrested later that night for soliciting a prostitute and Cybill is tormented by the tabloids.

Cybill convinces Ira to set Maryann up with Phil, a friend of his. Maryann is reluctant at first, but Cybill manages to talk her into going on a double date with her and Ira.