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

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 celebrates her first Christmas with the family.

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 is asked to turn one of his plays into a sitcom and the Sheffields might be moving to California. And her mother may be having an affair.

Fran checks into a man that her mother is seeing and coaches her father on spicing up their marriage.

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.

Mr. Sheffield wants to buy himself some time before his relationship with Fran grows, so he asks Fran to redecorate the kitchen. Fran invites her cousin Sheila over to help her, and Sheila proposes a special aphrodisiac decoration to give Fran a little push in conquering Maxwell's heart. But Fran finds the similarities between her life and her cousin Sheila's too big and fears that Mr. Sheffield will dump her after seeing the new decoration (exactly what Sheila's husband did to her). Fran decides then to do her own decoration, and Maxwell loves it.

Mai Ling, the Cambodian girl Fran and Val "adopted" in high school for 17 cents a day, is coming to NY to visit them. Sylvia doesn't like the girl, for whom Fran and Val fight over, resulting in a split up between the two best friends. Sylvia thinks Mai Ling will also come between Fran and Mr. Sheffield, but Fran finds out Mai Ling got engaged to Brighton to get a green card!

Fran goes to Maggie's school to have a word with her Philosophy teacher and ends up developing a crush on him. After having to ask Maggie for her approval, Fran starts dating the gorgeous Jewish bachelor, which, of course, upsets Mr. Sheffield (who won't do anything regarding his true feelings towards Fran). Fran lies about her age to Professor Steve, and later pays the price when his astrologist tells him he should be with a woman in her mid-thirties – C.C.!

Fran attends her high school reunion and is surprised to see that all her old friends are getting divorced, while she's the only one getting engaged. Trying not to be affected by all the negativity, Fran discusses with Maxwell the little things of life as a couple - which side of the bed they sleep on, what to do on the weekends, and how many children they'll have. That becomes an issue because Maxwell doesn't want anymore children, while Fran does. After realizing how much motherhood means to Fran, Maxwell says they'll plan it in the future, leaving them plenty of time to practice. Meanwhile, Niles goes through depression without having Ms. Babcock around to tease on; and Gracie gets scared she'll be sent away to a boarding school after a friend tells her it happened after her dad married her stepmother.

Maxwell's father unexpectedly passes away, and in his will he leaves everything to Concepcion, a secret daughter he had with a flamenco dancer. C.C. is back from the sanatorium and doesn't miss the opportunity of terrifying Fran and trying to split Fran and Maxwell up. Afraid that the Sheffields are going bankrupt, Fran visits Concepcion trying to persuade her to share the money with her siblings, but can't. Knowing what if feels like being poor, Fran tells Maxwell that she'll understand if he decides to marry a rich woman in order to keep his lifestyle. C.C. offers herself to marry Maxwell, but his love for Fran is beyond money. Then Sheffield's lawyer arrives with the news: Concepcion decided to share her money, all because Fran made her feel like family. Niles plays tricks on Ms. Babcock, making her doubt her own sanity.

A former model sets up a photo test for Maggie, but Fran is pushed out of the picture.

C.C. won't warm up to her father's offer of Streisand tickets, but Fran's hot to go in her place.

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

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.

Maxwell invites Fran to be his date at the very exclusive dinner party given by Elton John to celebrate Tantrums and Tiaras, the new film he and his partner, David Furnish, are premiering. Unfortunately, Fran's lurid past catches up with her when she appears in the film as the fam who prompted one of John's ""Tantrums"" by verbally abusing Elton. Yes, it's another Fine mess, and Fran--à la Lucy--goes to extraordinary lengths to hide her identity during dinner. Then, trying to hide her identity, she doesn't make a very good impression as Maxwell's date. Meanwhile, C.C. tries to cope with Maxwell's apparent preference for Fran over her.

Fran and Niles fight over who gets to ask Mr. Sheffield for the weekend off. Fran wins, and Niles accuses her of seducing Mr. Sheffield to get what she wants. He decides to get back at her and allies with C.C. against Fran. Finally, Niles and Fran forgive each other, and he suggests Fran takes Mr. Sheffield with her to the Fine Family Reunion at the Niagara Falls, the perfect place for him to propose and a solution that will give them both the weekend off. Unfortunately, Fran doesn't listen Mr. Sheffield's proposal. He slips and falls, with no recollection of what happened.

Fran's devastated after hearing from Dr. Reynolds she was never pregnant at all, that it was a false positive. Maxwell keeps hiding her pregnancy tests to avoid further sadness, and even invites Fran and her relatives to join him on his special appearance on the Hollywood Squares. Val, Sylvia and Yetta advise Fran to go see a herbalist to help Maxwell's swimmers. At the herbal store, Fran buys a special shake that will help Maxwell's little swimmers swim faster and some special cookies that will make them hot for each other. The shake doesn't help, so Dr. Reynolds prescribes hormones for Fran, who also buys an ovulation kit. Her timing couldn't be worse when she starts ovulating right when Maxwell is up on the squares. But nothing that Whoopi Goldberg's dressing room can't fix. Meanwhile, C.C. and Niles accidentally eat the special cookies and feel hot for each other, and Val quits her brightness pills because it was making her too gassy.

After Fran lends a college buddy of Maxwell's $1 million, she hears that he is broke and has been swindling others.