Umnhhh... according to
Gandalf, they were to be the longest talk of all his time.
‘But if you would know, I am turning aside soon. 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.’
Tolkien, J.R.R..
The Lord of the Rings: One Volume (p. 996). HMH
Books. Kindle Edition.
But considering Gandalf, that may not be saying much. Rather succinct, he tended to be..!!