Cybill tries to help Maryann, Rachel and Zoey overcome their romantic troubles by forcing them to take part in a new age drum beating session. Maryann, furious when Dr. Dick doesn't send any hateful gifts to her in honor of what would have been their 23rd anniversary, agrees to let Cybill take her to a new age female bonding session so she can get Dr. Dick out of her system once and for all. Meanwhile, Kevin uses Baby William to diffuse his anger towards Rachel and his job-hunting problems, and Ira finds out that Sean cheated on Zoey.

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 needs a favor from Dr. Dick's wife, Andrea (guest star Morgan Fairchild, reprising the role), so in return, she grudgingly agrees to give a speech at an awards banquet honoring Andrea. When Cybill discovers that Andrea can get Zoey a piano audition that's otherwise unobtainable, she agrees to give the testimonial speech for the charity award, which deservedly belongs to Maryann. But when Cybill finds out that Zoey got the audition on her own, she decides to tell the awards committee what she really thinks of Andrea.

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

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.

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.