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Truth
This poem never specifically mentions truth, but it's actually everywhere in "Up-Hill." If you look at the relationship between Speaker #1 and Speaker #2, you'll notice that Speaker #1 just seems to take all Speaker #2's answers for granted which is kind of a big deal. We mean, this journey sounds pretty dangerous. Is Speaker #1 really so confident that an inn will be waiting at the end of the road that he doesn't even want to get an address so he can GoogleMap directions?
Speaker #2 doesn't actually know anything, nor does he (or she) ever imply that what is being said is the truth. Speaker #2 is just trying to be a good friend and calm Speaker #1's jitters, the same way you tell your friend a big test or game will "definitely" go well, even if you know they didn't prepare as much as they should have.
Speaker #1 actually already knows the truth about his situation. The questions are all about confirming what he already knows. (That's a good thing, since Speaker #2 isn't exactly dishing out specific answers.)
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