Eonwe, you speak of somebody who is so wonderful and displayed I quote
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inner strength and fortitude
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and yet you said
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Cheating at the riddle game, eh? Well, i believe if you seach the records, you will find a blatnat attemp on behafe of Gollum to, yes, EAT (that would be canabolize!) Bilbo! Now, would you cheat at a riddle game to save yourself from dismemberment and consumption by a subterrainian creep?
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No if it were me, and I pride myself on inner strenght and fortitude, I would be upright and avoid cheating. Honesty knows no exeptions.
Now let's look further at his character. What does he leave as an heirloom? A ring of power that is bound to doom Frodo. What does this sweet old man do? He leaves him and his problems behind with young Master Frodo and hides out with the elves. The problem with Bilbo is he causes more problems then he is worth and never resolves his own problems. As is seen with the many relations that he had some hidden quarrel with. All of those 'gifts' he gave with their sarcastic and snide remarks. He causes the tension and yet didn't do anything to resolve it while still at Bag-End.