Maxwell volunteers Fran to produce Gracie's school play.

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.

After losing to Fran in tennis, Maxwell goes through a midlife crisis including dressing younger and buying a flashy sports car. Fran finally makes him realize his life is great, and the two of them go for one last hurrah in the sports car.

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.

Fran moves to her mom's because she doesn't want Maxwell to see her 24 hours before the wedding. Maxwell's sister arrives for the wedding and says their mother is not coming because she doesn't like Fran, which concerns Maxwell, but after awhile he gets over it, after realizing that it's not important. Fran goes to Jersey to pick up her sexy white negligee that she had ordered specially for their wedding night. On their way back, Val's car breaks down in the middle of nowhere, and Sylvia, Val and Fran have to spend the whole day waiting for someone to rescue them. Maxwell is visited by a very special someone: Sara, his late wife, who comes to wish him a happy marriage and confess that she sent Fran into their lives. Val's mother call Maxwell and goes to rescue them.

Niles shows Fran a script for a play he got from a friend of his. He wants to show it to Mr. Sheffield and become a producer so he can be something more than just the help. When pushed to tell why he wants to change his social status, Niles reveals to Fran he's in love with Ms. Babcock! Shocked, and yet merciful for her friend, Fran decides to take some money of her and Maxwell's joint account to finance the play. But neither Fran nor Niles have a name in the market, so they pass as C.C. and Maxwell and produce the play under Sheffield-Babcock Productions. Unfortunately, they're fined 250,000 dollars and find themselves with no solution but revealing the truth to Maxwell. Fran appeals to C.C.'s efforts to befriend with her (because Maxwell threatened to end their business partnership if she didn't solve her issues with Fran) to soft the shock. She's not so lucky with Max, who gets furious. Nevertheless, he helps them produce the play. After the premiere, Fran encourages Niles to tell h

Ms. Babcock finds Niles's proposal pathetic and laughable. Fran tries to contour the situation and teaches Niles a better way for him to start things with Ms. Babcock – call her by her first name, or take her out to a romantic dinner. During the dinner, Niles gets nervous and proposes two more times. C.C. won't let it go and keeps rubbing it into his face, until Niles is fed up and decides to quit, for he can no longer live under such humiliating circumstances. Neither Fran nor Maxwell can do anything to make him stay, and even C.C.'s promise to let it go count for nothing. Finally, Niles tells C.C. she's pathetic and lonely, and will spend the rest of her life waiting for a man that will never come, until one day she looks back and sees she wasted her entire life. Niles storms out and C.C. realizes what he said is true. She decides to move on and quit too. At night, while fighting over some dummy twins the doctor gave Fran, she and Max go to Niles's room and find him and C.C. sleeping