In "Sunday in the Park with Fran", Maxwell and C.C. try to curry favor with theatre critic Frank Bradley, and to do so, they (at C.C.'s insistence) make Gracie go on a playdate with his son, Frank Jr., despite Gracie's insistence that she doesn't like him, and Fran's support of her. During the playdate, Fran hits Frank Jr. with a baguette because he was bullying Gracie. So Maxwell and C.C. arrange a meeting for Fran to apologize, but when he proves incredibly hostile towards Fran, Maxwell decides enough is enough:
Maxwell: You know, Frank, I'm getting bloody tired of kissing up to you...
During "Here Comes the Brood" C.C upsets Gracie by telling her that Fran only spends time with the kids because she is paid to and only pretends to loves them. When Fran finds out she sits down with C.C and sets her straight doing so in the most polite but still awesome way possible.
Niles finally tells Maxwell exactly what he's been thinking since The Thing.
Maxwell: Niles, I don't know what [Fran] wants anymore! What am I supposed to do?
Niles: May I speak freely, Sir?
Maxwell: Yes, of course old boy...
Niles: I am so bloody sick of hearing this year after year: "Niles, what am I to do? I told her I love her, I took it back, I'm afraid of commitment, I'm worried about the children!" [Grabs Max] FOR GOD'S SAKE! MAKE A MOVE! DO SOMETHING! You passed on Cats! DO YOU WANT TO REGRET THIS FOR THE REST OF YOUR LIFE, TOO!?
Made better by what happens right afterwards. C.C. asks him what the shouting was about and he turns it to his favor.
Niles: I was trying to convince him to give up on Miss Fine and move on with his life.
C.C.: *rushing in* I agree with Niles! What're you waiting for? Just do it, do it, DO IT!
When Max and Fran finally get married and Sylvia finally gets the opportunity to stand at the altar as a maid of honor for her daughter. When the priest asks for the objection on why the two shouldn't be married, Sylvia turns to the audience with a face that would stop a bull in its tracks, just waiting for someone to make her day...
Niles: Look around you. They're married. They're starting a family. Where are you going to be 10, 20 years from now? You're going to be saying 'Merry Christmas' to your friends in rehab, and wondering what might have been!
Earlier on, Fran got her pretty good, too, namely by subverting Snark-to-Snark Combat. C.C. made her typical dig against her, and Fran merely retorts.
Fran: Why are you being so hurtful? I got nothing; I make minimum wage, there's no man in my life. I'm probably gonna die alone like a dog. Here (*hands Chester back to C.C.)
C.C.: Oh, Nanny Fine, I'm sorry. Oh, I feel just awful (*Leaves*)
Fran: (*Gives a sly grin to the camera*) Got guilt?
Maxwell finally beating Andrew Lloyd Webber with Yetta's Letters, a play about Yetta's life as an immigrant.