I've got another idea:
It's based on the "gleam in his eye and smile on his face."
Maybe Gandalf was doing an Aslan kind of thing: getting Aragorn himself to say that Frodo wasn't alone, instead of simply telling him. This way Gandalf knew who Sam was and remembered him, and is comforting Aragorn in a wise way, very in character.
Thing is, while Tolkien "borrowing" something from his friend C.S. Lewis isn't farfetched, I don't think it quite fits in the book. And I doubt Jackson would've used a Lewis reference.
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