The Long Talk

[Ancalagon'sFire]

‘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.’

The Lord of the Rings

What do you think Gandalf would have wished to discuss with Tom Bombadil prior to his departure from Middle-Earth? Bear in mind the enigma that Tom is (and Goldberry) and the fact they remained bound to Middle-Earth while Gandalf's time was spent within it. I have a theory on Tom and Goldberry representing the biological clock of Middle-Earth, but that can be developed later. For now, apart from the goings on in recent times did their conversation take a rather more dim view of the march of industrialisation, the impending ecological disasters created by the coming age of men or the did they simply while away the hours debating the natural order of things?

[Rumil]

Gandalf was surely as curious as the rest of us to know who and what Old Tom was

[Inziladun]

What Gandalf and Tom discussed is to me bound with the question of what Tom was. Bombadil's apparent uniqueness in the legendarium makes speculation especially difficult.
At the moment (because my thoughts on Tom's nature have varied), I'm of the mind that Tom could have been one of the Ainur who entered the world at a different time than the Valar (like Ungoliant?), and had his own 'assignment' from Eru that kept him out of most of the histories of the time. That, or like Radagast, he had his own agenda.
If that scenario is correct, I would say perhaps Gandalf needed someone to open his mind to, discussing all his hopes and fears, his failings and accomplishments; something of a 'confession' which would cleanse whatever weariness or negative feelings he had built up while being confined in flesh for so long. He would then be ready for his last journey homeward.
And what better 'Confessor' than one of the divine beings who had heard the music, but had sat outside as a neutral observer?
That's my theory, anyway.

[Alfirin]

As an extension of the "cofession" theory I've often though a big part of Gandalf's talk with Tom was to in a way get "permission" to leave ME, to have someone tell him it was okay to do so. Being clothed with the flesh of a man for so long would likely have led to Gandalf developing many of the mental quirks of being human and one of those quirks (at least for some) is a some doubt no matter how much one has actually done in service to others to qestion whether you have a right to ever stop, to say "I have done enough for the world, spent enough of myself in the service of others, I have earned the right to do this thing that I want." It's the bad side of being truly noble and unselfish (which Gandalf in his role in ME has clearly been) you feel a need to basically sacrifice yourself to the world , that being selfless means just that, having no self gratification at all, ever In that case what one often needs is someone outside of yourself who can give you permission to be selfish, to tell you its alright to be good to yourself, and that person has to be a person who you feel has the autority to do so. Given that at that point of "the talk" Gandalf is likely one of the, if not the, most powerful and higest level Maiar still "incarnate" and communcation with those in the blessed lands is impossible, Tom may be the only person who can fit that bill, the only spirit with the autority to give the absolution and permission that Gandalf needs to go to the West with a clean conscience.

[Ancalagon'sFire]

They halted and Frodo looked south wistfully. ‘I should dearly like to see the old fellow again,’ he said. ‘I wonder how he is getting on?’
‘As well as ever, you may be sure,’ said Gandalf. ‘Quite untroubled and I should guess, not much interested in anything that we have done or seen, unless perhaps in our visits to the Ents.

The Lord of the Rings

Makes you wonder though, if Tom isn't interested in the workings of men, the downfall of Sauron or the end of the age of the Rings, then where do his loyalties lie? Surely in the earth itself, the trees, the water, the shores, the stars and everything that was created and lasting, that is of course unless its very existence is threatened! What does Tom care about?

I'm sure Gandalf feels the need to unburden himself, but surely someone less 'seemingly' carefree and detached from the trials he had faced would be more suitable? Tom is altogether a different entity, but someone who Gandalf feels a connection with. The Maiar element is palpable in this meeting and as interesting as the workings of Men and Elves might be, just don't seem to be on the same level of debate I suspect these two were about to engage in. I imagine if one were present at the beginning and likely to be so at the end, then his conversation would be well beyond the parameters of bit-players in a very long saga.
Neither do I suspect Tom would be giving Gandalf absolution. In fact it would seem to me that was already granted upon his return following his apparent demise after the battle with the Balrog of Moria;

'Naked I was sent back – for a brief time, until my task is done.

I do not think Mithrandir needed to seek absolution from anyone.

[Inziladun]

Originally Posted by Ancalagon'sFire

Makes you wonder though, if Tom isn't interested in the workings of men, the downfall of Sauron or the end of the age of the Rings, then where do his loyalties lie? Surely in the earth itself, the trees, the water, the shores, the stars and everything that was created and lasting, that is of course unless its very existence is threatened! What does Tom care about? ;

Tom actually appears to know a great deal about the history of Middle-earth; he was aware of the Ring and its power, the Dunedain of Arnor, all the way back to the time of the Elves awakening. Just because he may not have played an active part in those histories doesn't mean he was oblivious to them.
Maybe he had become so enamoured of the 'natural' elements of Arda he was content to idly sit and watch time pass.

Originally Posted by Ancalagon'sFire

Neither do I suspect Tom would be giving Gandalf absolution. In fact it would seem to me that was already granted upon his return following his apparent demise after the battle with the Balrog of Moria;

I don't see it as absolution so much as Gandalf looking for someone to whom he could finally lay all his thoughts bare, leaving him at peace with himself and his finished task.

[Mirkgirl]

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:

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.’

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.