The scenario wouldn't allow that as a safe option with the spiders, orcs, and the ring which contains the soul of the dark lord himself. However in the case where a normal conversation was allowed I would tell him to throw the ring away no questions. Gollum used to be a hobbit until the ring turned him into that thing so that would be a goal. I would also keep the conversation a secret away from the dwarfs because i would've told Bilbo about how Thorin gets gold fever. I would then give him a lecture on history about the ring so it can be destroyed much sooner to solve a lot of problems.
I would then say that 13 dwarfs and a Hobbit can't do that much against a mountion sized dragon so it would be wise to find out how to hurt one and get a small army.
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