I always just assumed this was about Shanks finding out that Roger is dying, and wanting to ask him if it's true. Because we only saw him cry during the execution, and the whole Roger, Shanks and Luffy thing is that they only cry or are sad about someone dear to them, never themselves.
Just a thought
Don't ask me!
Just a thought
Don't ask me!
Oda is clearly saying Shanks asked him a question which was intentionally not revealed, indicating it's something we don't know. If it was that, then Oda would have just put the dialogue out there