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'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.

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.

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.

Finally, after 5 long years, the wedding day has arrived. Fran spends her last night as a single woman at her mom's house, where Sylvia reads her a letter she wrote to Fran when Fran was born. They both cry. Just a few moments before the wedding, Maxwell's sister Jocelyn tells Fran that the social differences between she and Maxwell will ruin their marriage as it did to hers. At the ceremony, Ms. Babcock tries to give it one last shot and pretends being the bride, but it doesn't work. Fran doesn't show up at the altar, leaving everybody apprehensive about what happened to her. Sylvia goes to her dressing room and finds Fran crying on the couch. Maxwell arrives and Fran tells him that their marriage will never work and decides it will be better if they cancelled it. Max tells Fran that what happened with his sister will not happen to them, because they love each other. He tells Fran all the wonderful things she has and says he will never get bored with them. The wedding proceeds, and Fr

Fran decides to spend her holidays away with Val, but this time just the two of them, no Mr. Sheffield, no kids, nobody but the two single gals. A hurricane hits the island, making Fran's dream vacations a living hell. She returns home early to find a lonely Maxwell, who later takes the entire family on a cruise around the Greek Islands.

After Niles is depressed about his life as a butler, he begins to act strange and while he is cleaning, he drops a piece of paper containing a list of items that convinces Fran that Niles is possibly a murderer due to his recent strange behavior and the contents of his list. A search of his room confirms her suspicions. During a stormy night, Maxwell takes the children out for dinner leaving Fran and Niles alone. Niles approaches Fran and she thinks Niles is about to murder her. He confronts Fran about how she knows what he is up to when in fact he is simply writing a play.

After watching Tasha's (a new female rock star) video on MTV, Fran decides to write lyrics of her own about her misery and suffering and make it big on showbiz. Discouraged by Mr. Sheffield, Fran decides to hand her lyrics to Tasha no matter what, and even passes herself as hotel maid with Val just to meet Tasha. When she finally does, Tasha is so interested in reaching out and listening to what the people have to say that she actually hangs out with Fran. Unfortunately, Fran's song is no good, but her misery is good enough for Tasha, who uses Fran as her muse – until Mr. Sheffield tells Fran he misses her and Fran turns happy, which makes Tasha turn to Val for inspiration (after all, Val lives with her parents, is over 30 and single).

Fran offers herself for the charity auction Mr. Sheffield is putting together with Bette Midler. A gifted 10 year old pianist, son of a big time investor, wins the auction and gets to have Fran as his babysitter for 5,000 dollars. Fran takes him to Yetta's retirement home and while entertaining the elderly with his piano skills, one senior collapses and dies in front of the kid. Shocked, he says he will never play again, and his father cancels the 5 million he promised to invest. Bette Midler goes to the mansion herself to teach Fran a lesson, but luckily Gracie picked up a few things from Fran over the past 4 years, which is enough to convince the kid to play again and his father not to back out on the investment.

The news of Danny's marriage to Heather Biblow makes Fran start buying everything she can. 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 and Val go to The Rosie O'Donnell Show and Fran is picked out of the audience to talk to Rosie. She's so natural and funny that Rosie asks her to come on the show as a regular guest to give parenting advises. C.C. jumps in as her agent, and Fran starts to have a taste of life as a celebrity. Maxwell gets scared of losing her and makes up a story about a dream he had where a ghost told him something horrible would happen to Fran if she didn't quit the Rosie Show. Fran gets fired and is replaced by a retired couple from Florida.

A woman calls Fran saying she might be her mother due to a mix up that happened in the hospital the day she was born. Doubtful, Fran goes to Sylvia to ask her about the day she was born, and finds out the story might be true after Sylvia says she left her for a moment while chasing for food. Terrified that her whole life might have been a lie, Fran invites the strange woman to her house, and for her surprise, she turns out to be black. Still, after Fran pays a visit to Lila Baker's huge mansion, Fran insists that she might be her daughter, since her late husband was Jewish, but the DNA test proofs not. Fran is really Sylvia's daughter, which is something Sylvia only gets after spending some time pleasuring herself with the wonderful food Lila has at her house. Meanwhile, Niles tries to convince Maxwell to sell one of his plays to CBS so C.C. has to move to LA.

After winning the Tony Award for play of the year - for "The Widower", beating his lifetime rival, Andrew Lloyd Webber - a tabloid starts to publish fake stories about Mr. Sheffield and Fran having an affair since Maxwell's honeymoon. Maggie is very upset about it, and won't believe it's not true. Fran's upset not by the fact that it's a fake story, but that the story said she was 40. Maxwell and Fran go to the tabloid to confront the journalist, but he assures them he won't print any more stories about them, since they were the lowest selling edition in 5 years! Meanwhile, Niles is upset because Maxwell didn't invite him to the cast party, and Dr. Miller convinces Mr. Sheffield to give him a "Butler of the Year" award.

Fran's high school classmate, Morgan Faulkner, is hired by Mr. Sheffield as the star of his upcoming play. This causes Fran to get a bit envy, seeing how Morgan's life turned out great while she is just a nanny. On top of that, Maggie decides not to go to college and become Morgan's personal assistant (just what Fran needed. She's rich, beautiful, famous, and now she's stealing her children!), but Fran manages to talk her out of it. Meanwhile, the entire family is invited to Passover at the Fine's, and Niles quickly learns the secrets of the Jewish cuisine.

Fran decides that even though she's marrying Maxwell, she still wants to work. She decides to help him with his new play. They have to find a rapper and Fran gets Sammy's grandson, who is a gift wrapper instead. In major trouble, Fran has to turn the nerd gift wrapper into a music rapper in less than 24 hours to prove to Mr. Sheffield that she is not stupid. Meanwhile, C.C. feels left out and replaced by Fran, and Niles doesn't let the opportunity of teasing her go away, until she finally goes nuts and is taken to a mental hospital.

Maxwell's father is in town and Fran decides to help end the Sheffield family feud inviting James Sheffield over for dinner. He brings Joan with him, his old secretary for whom he left Max's mother. Maxwell is outraged at his father's selfishness during dinner, while Fran keeps wondering why can't Maxwell act more like his father and marry the help.

Maggie receives a party invitation so Fran takes her to her favorite beauty salon. Fran gets a job there for an actress who loses a Sheffield audition.

Fran's aunt Freida has gone broke and moves into the Sheffield residence. The only way Fran can turn this around is if she convinces Freida's rich boyfriend Fred to propose to her. Fred doesn't think of himself as an exciting man, so Fran decides to teach him dance lessons. He has a heart attack and falls on Fran, just as Freida walks in. After the situation is cleared, everything seems to be fine again until Fred tells Fran he's in love with her. She almost puts a stop to the wedding, if Mr. Sheffield hadn't interfered. Fred has another heart attack, but this time everything ends up just fine.

Jay Leno leaves his dog under the cares of Mr. Sheffield. Meanwhile, Fran is being audited for her taxes, and not even flirting and champagne can help her out. She calls Mr. Sheffield for help, and they go to the INS office to prove Fran's income taxes. The hearing doesn't go too good until Jay Leno shows up, making the appeals officer happy enough to dismiss the case.

While Fran is trying to convince Maggie not to get a tattoo, Val slips in front of everybody that Fran got herself a tattoo when they were teenagers. Sylvia tells Fran she'll have to have it removed if she wants to be buried in a Jewish cemetery when she dies; and Mr. Sehffield is dying to know where her tattoo is. Fran, of course, faces that as another opportunity for romance with Mr. Sheffield, so she arranges the whole family to go on a trip to the Bermudas, where she can put on a tiny bikini and reveal where her tattoo is. But in the last minute she changes her mind, and the two have a very exciting ping pong game instead.

Danny Imperiali, Fran's former fiance, is dead. At his funeral (while comforting Danny's widow Heather Biblow), she meets a Jewish man who is ignored by his former lover's family and got nothing after he died. Afraid the same thing will happen to her, Fran stands up for herself and imposes Mr. Sheffield to do something. Afraid his grandmother (who's in town visiting), might judge him and remove him from her will, Mr. Sheffield does nothing, so Fran quits. When he realizes he might have lost Fran forever, Mr. Sheffield goes after her and takes back taking back saying he loved her.

Fran meets an incredible man at a singles bar. He's Jewish, he's a doctor, he's rich, he's everything Fran ever dreamed of in a man. But during her cousin's wedding - where she was a bridesmaid - Fran discovers that Mr. Perfect is her cousin! Seeing Fran devastated, Mr. Sheffield decides to send her to a therapist, and the therapist says Fran has an obsession about getting married. Fran decides to stop chasing men around, just to make Mr. Sheffield guilty.

Fran is shocked to learn that her biggest rival, Heather Biblow (who stole her fiancé and her job) is starring on her favorite soap opera, "The Young and the Restless". Heather invites Fran and Val over to her Malibu beach house, where she can rub it on their faces how successful she is. Fran and Val visit the studios, where they run across some of their favorite celebrities. Heather has a really hard time memorizing the lines, and Fran doesn't think twice before jumping at the chance of finally stealing something from Heather: her daytime TV job. Fran is hired to replace her, and calls the mansion saying she won't return. C.C. is happy at first, but quickly realizes she needs Ms. Fine back when Maxwell hires a new nanny: Heather Biblow. Fran is so upset with the thought of Heather in the house that she is fired from the show and returns to NY to get her job back.

Sylvia decides to invest in a condo in Boca. This much anticipated fact that should come as a blessing for Fran upsets her deeply, and Dr. Miller says it's because deep down she doesn't want her mother to leave. Mr. Sheffield thinks if he takes Fran to see the condo she'll accept the idea, and just when Fran finally realized how much peace she'd get from that, they discover there isn't any condo, only a swamp. Fran's devastated (specially when Sylvia interrupts her fantasy from coming true), but at least she won't have to separate from her mother yet. Meanwhile, Niles feels bad for being the only one of his friends who's still single.