: I think Gandalf merely says this to specify that he'll be relaxed and have as much time as he wants to chat with such an interesting being as Tom, not that Tom will have anything particularly earth-shattering to tell him. Tom is such a character, and has such a different take on his life because he hasn't been involved directly in any of the wars and he doesn't acknowledge any power over him, or that he could have power over anything else, that Gandalf will welcome such a different outtake on life, especially after his supreme efforts to save just such beings as these from oblivion. And because Tom's been around so long they can connect in ways that Gandalf only could with other Maia, as opposed to for example Hobbits. But that's only my opinion!

For what it's worth, I think Patience has the right view of the subject. Sometimes you can read too much into these things. Gandalf has not had a "long talk" with anyone for a long time because his tasks have consumed such time and energy as he has had. His mission is fulfilled; his tasks are completed. Any talks or conversations he carries on now need have no great end, such as the downfall of Sauron, in view -- which has ALWAYS been the case with Bombadil.

Oberon