How Did Gollum Lose the Ring?

[Boo Radley]

Well, obviously we all know how he lost the ring, but what I'm asking is how could he have ever been so careless as to LOSE THE PRECIOUS??!!!
I'm surprised he wasn't aware of it's location every waking moment. You would think that as he was completely obsessed with it, he'd be touching it at every opportunity just to reassure himself it was where he expected it to be.
And I know that the time had come (Or almost come) for the Ring to "be found", as it were, so do you think there's a possibility that the ring could have... I don't know... clouded Gollum's mind somehow? Whispered to him and given him a false sense of security, so that perhaps he wasn't constantly touching it and reassuring himself as to it's proximity?

Or, going the other direction, do you think that as Gollum had been alone for so long and the Ring had become so much a part of his life/personality/what-have-you, that he... didn't necessarily take it for granted, understand, but rather couldn't conceive of it being anywhere else than where he kept it, and so the need to constantly check it and make sure it was safe, wasn't really a factor.

I sort of lean towards option B, myself.

[Legate of Amon Lanc]

Your question is answered by Gandalf to Frodo at the beginning of LotR, in chapter 2, "Shadow of the Past":

A Ring of Power looks after itself, Frodo. It may slip off treacherously, but its keeper never abandons it. (...) It was not Gollum, Frodo, but the Ring itself that decided things. The Ring
left him.
(...) "The Ring was trying to get back to its master. It had slipped from Isildur's hand and betrayed him; then when a chance came it caught poor Deal, and he was murdered; and after that Gollum, and it had devoured him. It could make no further use of him: he was too small and mean; and as long as it stayed with him he would never leave his deep pool again. So now, when its master was awake once more and sending out his dark thought from Mirkwood, it abandoned Gollum."

The same thing happened to Isildur: he was swimming with the Ring on, and surely he handled the Ring with great care, because in contrary to Gollum, he even knew what he's actually holding! Nevertheless, suddenly he realized the Ring is just gone. The same must have happened to Gollum.

(Just to note, the point of the passage from which I picked quotes above is about something else, but for our needs I picked these to explain the Ring's leaving of Gollum.)

Also, to explain more of how Gollum handled the Ring, a quote from the Hobbit:

Gollum used to wear it at first, till it tired him; and then he kept it in a pouch next his skin, till it galled him; and now usually he hid it in a hole in the rock on his island, and was always going back to look at it. And still sometimes he put it on, when he could not bear to be parted from it any longer, or when he was very, very, hungry, and tired of fish. Then he would creep along dark passages looking for stray goblins.

With this corresponds also another word of Gandalf's from the Shadow of the Past:

For it was long since he had worn it much: in the black darkness it was seldom needed.

[Boo Radley]

OK. That much is known from the stories. (And thanks for all the quotes. Very thorough work on your part.) But, I guess what I'm trying to ask is what transpired in order for Bilbo to happen upon it? Was Gollum wearing it away from his island and it slipped off his finger? I can't buy that, because surely he'd be aware of that happening. And even if he somehow was oblivious to it no longer being on his finger, why would he rush back to his island to look for it? Well, maybe I can understand that. Who of us hasn't gone back over the same ground numerous times in the vain hope of finding something we've lost, even when we KNOW it aint where we're looking?
"Honey, you've looked for your keys on that end table a dozen times! You know they aren't there!"

Did he then go back to wearing it in a pouch and it fell out?
Did the Ring grow little, tiny feetsies and go for a stroll on it's own?

Maybe it did cloud his mind a bit, so for a short time, he wasn't obsessed with it. But I wonder how long it was out of his possesion before Bilbo happened upon it.

I know it's not really important, but I just started wondering how a creature so consumed with something could not be aware of it's absence.

[Morwen]

Maybe it did cloud his mind a bit, so for a short time, he wasn't obsessed with it. But I wonder how long it was out of his possesion before Bilbo happened upon it.

I don't think it could have been out of his possession for very long i.e. more than an hour or so. As Legate points out, though Gollum no longer wore the Ring frequently, he still needed to check on it constantly.

This need to constantly check on his Precious leads me to think that the period of time between Gollum losing the Ring and Bilbo finding it must have been short indeed. In the same way that a Ringbearer can be fiddling with the Ring and not be immediately aware that he is doing so (e.g. Frodo at the Prancing Pony), I think that he can likewise lose the Ring and not immediately be aware that it's gone (perhaps due to some "clouding of the mind" caused by the Ring). Therefore at the time that he meets Bilbo, Gollum probably has not had sufficient time to register his loss and then he is distracted by his curiosity, wanting to find out what Bilbo is and then later by the Riddle Game.

As for why it doesn't immediately dawn on him after the Riddle Game that he has lost the Ring? I think this might be explained by : (a) he was upset at losing the Game which (b) caused him forget that he was supposed to have the Ring on him and instinctively head towards the island, the place where in recent times he is used to keeping it. I don't think that this "forgetting" is necessarily connected to the Ring but is similar to forgetting that my cell phone is in the laptop case and instinctively searching my handbag where it normally stays.

[Legate of Amon Lanc]

Originally Posted by Morwen

I don't think it could have been out of his possession for very long i.e. more than an hour or so. As Legate points out, though Gollum no longer wore the Ring frequently, he still needed to check on it constantly.

This need to constantly check on his Precious leads me to think that the period of time between Gollum losing the Ring and Bilbo finding it must have been short indeed.

Precisely. From the sources we have, we know that it was "just a few hours":

Originally Posted by The Hobbit

Only a few hours ago he had worn it, and caught a small goblin-imp.

[Bêthberry]

How did Gollem lose the Ring?

Dropped call? Tired of the dialtone?

Sorry, I now return you to serious topic.

[Boo Radley]

So, we figure the Ring sensed Bilbo's presence and figured he was it's best hope for getting out of there?
Sounds resonable to me.

Scary, but resonable.

[Morwen]

Originally Posted by Boo Radley

So, we figure the Ring sensed Bilbo's presence and figured he was it's best hope for getting out of there?
Sounds resonable to me.

Scary, but resonable.

Gandalf thought that Bilbo was meant to find the Ring and not by its maker. So there may have been other powers at work allowing the Ring to leave Gollum and find Bilbo.

[Legate of Amon Lanc]

Actually, it was not the will of the Ring to go to Bilbo. This is what I said about the quoted passage, that what I quoted wasn't the main point of the debate. For the question how it was posed at that time, it seemed sufficent. But okay, if you mention this, I'll find even the rest According to what Gandalf says, there was "another power at work". The Ring wanted to get out of the cave, but...

..."What, just in time to meet Bilbo?" said Frodo. "Wouldn't an Orc have suited it better?"
"It is no laughing matter," said Gandalf. "Not for you. It was the strangest event in the whole history of the Ring so far: Bilbo's arrival just at that time, and putting his hand on it, blindly, in the dark.
There was more than one power at work, Frodo. The Ring was trying to get back to its master. It had slipped from Isildur's hand and betrayed him; then when a chance came it caught poor Deal, and he was murdered; and after that Gollum, and it had devoured him. It could make no further use of him: he was too small and mean; and as long as it stayed with him he would never leave his deep pool again. So now, when its master was awake once more and sending out his dark thought from Mirkwood, it abandoned Gollum. Only to be picked up by the most unlikely person imaginable: Bilbo from the Shire!
Behind that there was something else at work, beyond any design of the Ring-maker. I can put it no plainer than by saying that Bilbo was meant to find the Ring, and not by its maker. In which case you also were meant to have it. And that maybe an encouraging thought.

I think I have to add here that interestingly, for some really unexplainable reason I somewhat uncosciously "skipped" this part for many years, meaning that when reading it, it didn't ultimately come to me what it actually means. I never even thought of it - I didn't even pose myself any question, you know, like "how come that Bilbo was meant to have it"... I just never thought of it. While it is surely an important moment, for Frodo at least. But here you see, there was "something else at work", not just the will of the Ring - Bilbo was meant to have the Ring, and it was not the design of the Ring's maker. Intriguing.

[Boo Radley]

You know, I had completely forgoten about that speech by Gandalf.

That is interesting!