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Alright, now I understand!
also the best joke contender for me is about singing on a stage in a bathtub
The key difference between how they both said “watching” is context. Scootaloo is doing some literal watching while the Mayor is doing so figuratively. Scootaloo, in ignorant child-like bliss, mistook this as the literal form of the word. And thus creates the best joke in the whole movie.
Scoots: So we’re watching the box for her.
Sweetie: We didn’t do a thing and let a person do a thing, anything! Want a cookie?
Mayor: Oh no, I’m watching my figure.
Scoots: Watching it do what?
My point is, Scoots is acting like she’s puzzled by mayor’s line, even though mayor’s line is essentially the same as the line Scoots herself said two lines before that.
~somewhere in an alternate universe~
Scoots: So we’re watching the box for her.
Mayor: Watching it do what?
I don’t see how it doesn’t fit. The context was basically:
Sweetie Belle: “We didn’t [insert the plot and what happened to the star here] or anything! [pause] …Want a cookie?”
And this is the dialog that followed.
That, or she was just messing with the mayor.