First think about a possibility to talk with Tom... about any- and everything you want to know...
Now let us concentrate on the exact words:
Quote:
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I am going to have a long talk with Bombadil: such a talk as I have not had in all my time. He is a moss-gatherer, and I have been a stone doomed to rolling. But my rolling days are ending, and now we shall have much to say to one another.’
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Gandalf's part in Middle-Earth was always rushing here and there... and he would have probably thought of more questions than you. And Tom being rushed wouldn't work.
I always thought the conversation was kind of award for Gandalf, to learn everythig he always wanted to know from Tom, without having to keep the clock in eye.