- When George bumps into Pollyana and Nancy while they're out shoping and grabs Nancy and kisses her.
Nancy: Oh! George, stop it! Oh, Pollyanna, you don't know my cousin Fred, do you?
George: Your cousin Fred?
Nancy: This is Miss Harrington's niece. (pointedly) The one who's come to live with her!
George: (realizing whats going on) Oh! Oh, that one! Well, hello, Pollyanna, how are you?
Pollyanna: Fine, thank you.
George: Well, how 'bout this? Running into you after... what's it been, six years? Say, how's your ma and pa?
Nancy: Why, they're just fine.
George: You know, Pollyanna, I don't take too much to relatives, but this girl was always just like a sister to me. I tell you, I love, love this cousin. (kisses Nancy again much to her chargun)
- When Edmond found Pollyanna hidden behind a plant during the town meeting.
Edmond: Hello. Is this the town meeting?
Pollyanna: Oh, no. It's in there. In the conservatory, for heaven's sake.
Edmond: Oh. Are you one of the Ladies Aide?
Pollyanna: Oh, no. I'm just a child. I'm not even supposed to be here! Sh!
Edmond: What's your name?
Pollyanna: Pollyanna Whittier. That's my aunt over there, the pretty one. This is her house, and I live with her.
- "Brimstone and Damnation on top of ham and eggs."
- Loved it when George and Nancy trick Pollyanna with reverse psychology so they can go on a date, and bring her along.
George: How'd you like to go down the street and get a great big dish of ice cream, my treat? Oh, no, that's a rotten idea. She probably hates the stuff.
Pollyanna: Who, me? Oh, no, I love it!
George: No kidding? How'd you ever develop a taste for that awful stuff?
Pollyanna: Oh, no, really! I really do love it!
George: I know the perfect place. Come on, girls, follow old Cousin Fred to the land of strawberry frappe. Unless you'd rather go down the street and have a beer?
Pollyanna: You're funny.
- Pollyanna was also not fooled by the 'cousin Fred' ruse and busted Nancy immediately. However the film goes on for a while before Pollyanna sees George again. The next time she does, she calls him George. After a moment he does a Double Take and realises that she shouldn't know his name.
- There's also Pollyanna's complete obliviousness that Mr Prendergast does not want her in his house at all. Every other sentence is him begging her to leave, but she just doesn't get it. They pretty much become good friends because Pollyanna doesn't cop that he wants her out of the house.
- Mrs Snow, who receives food from all the women of the town to help her convalescence, always complains that what she got isn't what she wanted (e.g. if she got calf's foot jelly then she'd says she wants chicken, and if she got chicken she'd say she wants lamb broth). Pollyanna eventually "wins" by bringing Mrs Snow a little bit of everything, thinking it'll make her happy that she finally got what she wanted that day. She never realizes that Mrs Snow just likes to complain.
- And in the film, Nancy says hypothetically that Mrs Snow would probably want chicken instead of jelly. When Mrs Snow complains that she wanted lamb broth, Pollyanna (not quite understanding) 'corrects' her by saying she should want chicken instead.
- Mrs Snow's Establishing Character Moment is also quite funny. Pollyanna and Nancy arrive at the house and exchange pleasantries with Millie. Then we hear Mrs Snow's voice screaming from the other room - "Stop that noise in there! Haven't you any respect for a dying woman!" - Millie and Nancy don't bat an eyelid at this.