Aragorn not approaching sooner

My question is,
Why did Aragorn not approach the company after seeing them from the hedge where they left Tom?
He obviously knows Bombadill by both looks and name since he said he was watching them take their leave of Tom.
If he knows Tom or even about him, and I don't doubt he does, he can hardly believe the company would be frauds (set to trap him). No doubt Tom would not be easily deceived by a fake company, and if Aragorn knows about Tom he must know this too.
So why does Aragorn let the moment pass him by, Tom could vouch for his identity to frodo and the rest.
Why wait until Bree?

"A lot of trouble would have been saved if you had let him in" - Aragorn
"Yes, but a loads more trouble would have been saved if you hadn't been birds nesting in a hedge" - Barliman
 
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From Strider's perspective, depending on how well he knows (or knows of) Tom, who knows what Tom would do, or why?

And Strider has probably been living rough for some time now, and would look even more the scoundrel than he will later.

(These are not slam dunk answers, just suggestions.)
 
Yes, that is true. But I think Tom would see under the scoundrel (if he doesn't already know of Aragorn, which it kinda seems it does)

"Now, I was behind the hedge this evening on the Road west of Bree, when four hobbits came out of the Downlands. I need not repeat all that they said to old Bombadil"

It seems by that remark about Tom that they are known to each other. Perhaps not introduced, but "old Bombadil" seems to me to be a name of fondness from Aragorns part. Perhaps Tom doesn't know Aragorn, but at least I personally think Tom can see through everyone. I don't see anyone lying and getting away with it to ol' Tom
 
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Tom must certainly know Aragorn or at least of Aragorn:

'Few now remember them,' Tom murmured, 'yet still some go wandering, sons of forgotten kings walking in loneliness, guarding from evil things folk that are heedless.'

The hobbits did not understand his words, but as he spoke they had a vision as it were of a great expanse of years behind them, like a vast shadowy plain over which there strode shapes of Men, tall and grim with bright swords, and last came one with a star on his brow. Then the vision faded....
 
My guess: Aragorn did not to attract attention by approaching the hobbits out on the public street, and he wanted to observe them before committing himself.
 
But that was the road outside of bree. If the company was open about saying things like "I am mister Underhill if any name must be given" (paraphrasing) then it can hardly be anyone else then the company and Tom on the road
 
I suspect Aragorn was relatively convinced that Frodo et al. were who he was looking out for, but he was just being cautious. No sense in taking risks. And I thinkthe broad sweep of his interactions with them in the Prancing Pony show that he wsn't ever truly conviced they wereprobably sent to catch him.
 
I believe that Strider wanted the right moment. The right timing.

I think that Aragorn knew it wasn't simply a, "Hello, my name is..., I know Gandalf, etc." and they quickly continue on. The dialogue in their private quarters at the Prancing Pony shows that simply saying things or who knew whom wasn't going to be the definitive proof needed for trust to be obtained by either Strider or the Hobbits.

So, Aragorn knew he needed a true sit down with the Hobbits, to make it as short as possible but a sit down nonetheless and probably not one out in the open, regardless of the territory because he also knows of what pursues the hobbits. Aragorn knows the Hobbits are going to the Pony and he says that the Nazgul cannot attack the Pony. So, I think that in Aragorn's mind the Pony is the best place to lay down his case to the Hobbits and hopefully with proper time to do it in.

My only thought about Bombadil is that Aragorn might think Tom unpredictable, even if he knows Bombadil well or not, and that he wouldn't want any extra cooks in the kitchen as it were in this important moment of gaining the trust of the Hobbits and proving to them that he can lead them further on in their quest.
 
What if Aragorn is utilizing a related strategy to Gandalf introducing the Dwarves to Beorn? An introduction with gradual reveals, and incrementally increasing levels of information, in order to maintain interest and not reach the conclusion too soon.

I'm not saying this is what I think it is, just putting it out there as yet another possible idea.
 
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