Sorry, double-post. I also agree with that. There is a theory - from Dominic Armato himself, actually - that Boybrush is actually him from the past.
Like MI2 insinuated, he was an orphan imagining stuff while going to an amusement park. While growing up, it got difficult for him to differentiate reality and fantasy.
Him talking to his younger self is a way for him to finally let go. Elaine and Boybrush leave and he’s alone on his bench, finally at peace.
Of course, it’s just one interpretation.
I love that the game allows us to have multiple ones… and all of them could be correct.
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