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Nobody is asking Will to say things in a straightforward manner, but he still needs to provide an answer that it's an answer.
He basically is supposed to give an answer in the form of a riddle, however some answers not only aren't really good as riddles since their meaning is quite apparent, they do not provide any answer at all, or they aren't really pertinent to what he's supposed to answer.
I think he did quite well for EP1 and EP2, but after that it seems he doesn't even bother anymore.
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