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.

C.C. makes a bet with her brother that he can't get Fran to play Jeopardy!. But Fran somehow enters the game and manages to win! Meanwhile, Mr. Sheffield is driving himself crazy for not being invited to the Renaissance Weekend held by the president, and Fran gets him tickets with the new next door neighbor, Roger Clinton.

Fran's been going out with a rich, handsome Jewish doctor named Julius Kimble. After only 2 weeks, he asks her to marry him. Although having some doubts about it, Fran accepts after Sylvia pushes her into doing it. When they go out to buy Fran a ring, Julius disappears and takes the very expensive ring with him. Turns out he was just a thief and now Fran is left all alone. She blames her mother for the disaster and the Fine women end up going to a shrink to solve their problems. Back at home, both Mr. Sheffield and Fran complain about the lack of single attractive people for them to date.

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.

Feeling that taking care of the kids has taken over her life and eliminated her personal life, Fran thinks about moving out of the mansion. But the real push is given by Mr. Sheffield who assures her she can't do it. So Fran and Val move in together to a very small apartment in a building full of gay men. Fran misses the mansion but doesn't want to give Mr. Sheffield the pleasure of being right. What she doesn't know is that he is also dying for her to come back. So they secretly ask for Sylvia's help, and Fran finally moves back to the mansion.

The news of Danny's marriage to Heather Biblow makes Fran start buying everything she cans. After being confronted by Mr. Sheffield, Fran enters shoppers anonymous, but has a very tough time giving up shopping, until an unexpected kiss from Mr. Sheffield cures her miraculously.

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.

Mr. Sheffield and C.C. are going to Boston for the weekend, but what originally started as a romantic getaway plan for C.C. turned into family weekend thanks to Niles. Fran, Maggie and Niles have the house to themselves, and Fran decides to throw a singles party at the house to fish an eligible bachelor. But the party is over when an undercovered cop shows up and arrests Fran for not having the required licenses. After spending the night in jail, Fran returns home and Mr. Sheffield almost fires her, if it wasn't for Maggie stepping in and taking the responsibility for the mess. Fran goes to court, but Mr. Sheffield shows up in the last minute to help her from her senile lawyer, Uncle Mannie.

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.

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.

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

Fran gets a date with a guy named Tony Tattori, who later she discovers to be on the mob. Scared to death that her life might be in jeopardy, Fran doesn't have the guts to break up with him, and Mr. Sheffield decides to do it for her. Lucky him C.C. accidentally dumped Whoopi Goldberg from their show and they needed a singer and Tony was very interested on being on Broadway... Meanwhile, Brighton steals Maggie's diary and makes her his personal slave until Fran comes up with something that will get her out of that situation.

Mr. Sheffield rushes Fran to get ready because they're late for a premiere. Fran worries about her purse not matching her dress, but Mr. Sheffield assures her no one will notice. But Fran appears on Gloss Magazine as a "fashion don't" and blames Mr. Sheffield for it since he was the one who didn't let her change the purse. So to make things up, he hires her as the costumer for his next play. What was set for disaster turns out to be quite a hit when Fran asks her cousin, renown designer Todd Oldham, to design the costumes with her.

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.

When her mother throws her father out of the house, Fran seeks advice from her grandmothers. She also thinks that Mr. Sheffield needs a change in his life.

Val's new boyfriend starts to move in on Fran.

Thinking Mr. Sheffield wants her to be her valentine, she puts up a billboard in Times Square.

When Sylvia decides to have plastic surgery on her arms, the doctor tells her it's normal at a certain age for body parts to grow. Fran's feet modeling agency reunion is coming up, and Fran starts to freak out about her age and the fact that her feet have gone up a whole size. Luckily, she has Mr. Sheffield, who volunteers to escort her to the reunion.

Mr. Sheffield has Elizabeth Taylor over, and like with all celebrities, Fran can't control herself until she meets her. A very friendly Elizabeth asks Fran to take her black pearls necklace to a courier, but of course Fran has to do it in her own way. She takes a cab, and accidentally bumps her head against the window when the driver misses a red light. She is taken to the hospital and wakes up with amnesia. She thinks she's Mrs. Sheffield, and after her she remembers what happened she finds herself in a lot of trouble when she realizes she lost Elizabeth Taylor's pearls.

Fran starts to date Michael LaVoe, a famous hockey player for the NY Rangers. Mike is very superstitious and blames Fran for losing the game when she wears red shoes to the stadium. The entire city thinks she's a jinx and she decides to prove him wrong. But did the red shoes really jinx the game?

After Fran beats him in tennis, Maxwell is feeling old and goes out and buys a younger image and a sports car.

Fran goes out with the new temple cantor, Gary. When Mr. Sheffield listens him singing, he hires him to be on his next play. He quickly promotes the cantor to the lead of the play after the original actor is run over by a bus, and Gary decides to quit the temple to dedicate his time to his Broadway career. Everyone blames Sylvia and Fran for it, and they start to be ignored at temple. Sylvia throws a curse on Fran and everything starts to backfire until Fran donates the $500 she got from the air company to temple.

Brighton is failing French in school so Mr. Sheffield hires a tutor for him. His tutor is incredibly good looking and attractive, and Fran wastes no time in flirting with him. He quickly proposes to her, something Mr. Sheffield thinks is quite suspicious since he doesn't have a green card. But Fran doesn't listen to him until she finds out Philippe has made a pass on C.C. and only proposed to her to stay in the country. She dumps him and Mr. Sheffield takes Fran out to console her.

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

Fran runs onto Mr. Sheffield's plane with his bag and ends up having to go to Paris with him. On the flight back as the plane is plummeting down he tells Fran that he loves her.