Maggie is a candy striper at the hospital. When she takes off to go on a date, Fran fills in for her and must shave Maxwell for an appendectomy.

Fran strikes up a friendship with a male nanny whom she erroneously assumes is gay.

Fran worries about her future when Mona, one of her fellow nannies, retires to Florida. The night of Mona's goodbye party, Fran gets drunk and staggers into Maxwell's bed.

When Maxwell's mother wants him to get rid of Fran, Maxwell reacts by proposing to Fran who makes him feel very guilty for using her.

Maggie's 16th birthday is approaching and Fran intervenes in her father's plans for her party. Instead of a boring party at the Guggenheim Museum, Fran convinces Mr. Sheffield to have it at her aunt Frieda's bar. While the place is not nearly as fancy as the museum, Fran has to solve a very important family feud before the party can happen: her mother and Frieda haven't spoken to each other since 1979. The two make peace, but when Frieda comes out of the bathroom, her butt is showing and she blames Sylvia for the same embarrassment when they first fought. They start a food fight which quickly spreads to the whole party in a huge food war. When Mr. Sheffield walks in, he is shocked to see that scene and just when he's about to twist nanny Fine's neck Maggie thanks him for the best party ever.

C.C.'s vision for a romantic weekend hit a snag when she and Fran end up locked inside Maxwell's wine cellar together.

After Brighton joins Sylvia's canasta team, Fran is dumped from it.

Maxwell hears Niles singing and asks him to sing for his backers' audition. Meanwhile, Fran clashes with her sister Nadine.

Grandma Yetta stays with Fran and the Sheffields while her retirement home is being fumigated.

Maxwell draws up a will which states that Fran will remain nanny in the event of his death. Meanwhile, she thinks that a fax of a potential client's heart-sensitive diet given to Niles is really for Maxwell.

After many years of exchanging letters, Fran's pen pal Lenny wants to meet her. But Fran is worried because over the past years she exaggerated a little on the lies and now is concerned that Lenny won't like her for who she really is. But Mr. Sheffield pushes her to attend the date (more because he wants to see Lenny than because he wants Ms. Fine to meet him) and waits for him with her at the Russian Tea Room. But Lenny never shows up and leaves a note at the door saying he couldn't possibly compete with such a good looking guy she was with (Mr. Sheffield). Meanwhile, C.C. arranges to work late just to seduce Maxwell, and Niles plays with her. Bored, the two have a few drinks and have their first romantic kiss after calling each other names.

Fran tells Mr. Sheffield he should retire his wedding ring, and after C.C. points out that Andrew Lloyd Weber was featured in the paper's crossword puzzle, Maxwell decides to get a publicist to improve his image and make him more popular. He hires the gorgeous Sydney Mercer and radically changes his image to a middle aged bad boy. He starts to fall for Sydney, causing both C.C. and Fran to get jealous. They set a date in the Rainbow Room but Fran discovers in the last minute that Sydney is gay, and more interested in her, so she rushes to meet Mr. Sheffield, but they end up getting stuck in the elevator.

When Fran catches Maggie smoking, she herself pretends to smoke so that Mr. Sheffield can teach her a lesson in front of Maggie. But Mr. Sheffield overreacts so Fran leaves their home. Mr. Sheffield remembers all the great times together (seen as flashbacks), but eventually realizes what she was trying to do and wants her back.

Maxwell dates a woman with a striking resemblance to Fran.

A man whom Fran snubbed in high school has written a play and threatens to jump off a ledge unless Maxwell reads it.

Fran gives Maxwell a stock tip that turns out to be from a hot dog vendor.

Fran suggests that Maggie might go to a kibbutz in Israel for the summer instead of a convent.

Fran decides to take a cruise to meet guys and Mr. Sheffield and family join her.

Niles poses as Fran's husband to impress her visiting relatives.

Fran has a run-in with the son of the town's toughest critic, and that could be catastrophic for Maxwell and CC's new play.

Maggie's tyrannical gym teacher turns out to be Fran's former teacher. Maxwell hires an abrasive megastar.

Gracie's Red Robin troop goes to Grandma Yetta's retirement home to "adopt" a grandparent. When Gracie's first and second picks pass away, it sours her on scouting.

On the subway, a Russian immigrant accidentally leaves her baby, and Fran picks it up, believing it to be abandoned.

A director plans to sabotage his production of "Romeo and Juliet" by casting Fran in the lead role.

Brighton faints while filming Fran's cousin's bris and Fran sends it to Hollywood. Everybody visits Hollywood and Fran keeps getting thrown off the Doctor Quinn Medicine Woman set.