How bored are you?

[Gwaithmir]

It would have to be a meeting that took place after the War of the Ring, since Gandalf was at or near Isengard at the time Frodo brought the One ring to Bombadil's house. Near the end of The Return of the King Gandalf expressed a desire to visit Bombadil, although I can't recall the reason for such a visit. However, it might have entailed a discussion on why the One Ring was not left in the woodsman's care and what eventually became of it. I will seriously consider your request. 

The link to my Middle Earth stories may be found on my profile page.

Bombadil keeping the ring was discussed at the Council of Elrond, and was generally agreed to have been a bad idea - the most likely outcome was that Tom would forget about the ring or simply throw it away. Glorfindel opined that it would simply postpone the inevitable, as it was uncertain that even Bombadil could hold out against Sauron.

Gandalf, who arguably knew Bombadil better than anyone, argued that he might take the Ring '...if all the free folk of the world begged him, but he would not understand the need.'  I doubt very much that Gandalf alone could have convinced Bombadil to take the Ring.

Boru

Which is why I think a post war scenario in which Gandalf and Bombadil discuss the Ring over a pint of ale would make for a better story. It would also make for an interesting sequel to my tale King Oak.