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 decides to stop chasing men like Dr. Miller told her. Sylvia doesn't like that at all and blames Mr. Sheffield for her daughter staying single forever. Fran, Val and Ms. Babcock decide to go out together on a "girls night", with no pressure to find a man, but after Val and C.C. get dates, Fran finds herself as a fifth wheel on their double date. Alone, embarrassed and depressed, Fran goes home trying to act as if she had a great time with them, but can't. Once again, Mr. Sheffield and Fran find themselves alone, comforting each other. Meanwhile, Dr. Miller tries hypnosis with Sylvia but that doesn't go too well.

Fran freaks out on Mr. Sheffield after he brings home a model and makes out with her in the living room. Dr. Miller says Fran is upset because she is thinking of Maxwell as her husband, not as her employer. At the movies, she runs into Dr. Miller, but is shocked to see him picking his nose. She is so disgusted that she thinks of never seeing him again. Mr. Sheffield worries about her and confronts Dr. Miller about his actions, but gets very embarrassed when he finds out the "inappropriate behavior" Sylvia told him about wasn't what he had in mind. Meanwhile, C.C. is dumped by her boyfriend and asks Niles to escort her to an awards show, and the two end up having a very pleasant night out.

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.

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.

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!

Upset about Yetta's upcoming wedding, Fran is advised by Dr. Miller to focus her energy on new life projects. She decides to pursue an old dream of becoming a weather girl, and thanks to Sammy, who's Bryant Gumbel uncle, Fran scores an audition for editorial commenter of Public Eye. Mr. Sheffield doesn't like the idea of Fran leaving the house, so he sets up a scheme with Gracie to convince Fran into quitting her new job. But they don't have to do that, Fran ruins her audition by herself (by mistaking gene therapy with therapeutic jeans). Meanwhile, Sylvia has problems accepting her soon-to-be stepfather.

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 decides to take her father to a basketball game, but he refuses to go knowing the tickets came from Mr. Sheffield. Confused, Fran goes to Dr. Miller for advice, and he tells her she's always looking for men like her father – that will keep a distance between them. Fran decides then to make Mr. Sheffield change, and when that doesn't work, she decides quit her job and change herself. Not wanting to let her go, Mr. Sheffield – Maxwell – calls her Fran. Although they agree on not doing it in front of others yet, Max and Fran take their first step on the road of commitment.