Today in Middle-Earth: Gollum visits Shelob, but seeing Frodo asleep nearly repents (March 11th, 3019 T.A.).
And so Gollum found them hours later, when he returned, crawling and creeping down the path out of the gloom ahead. Sam sat propped against the stone, his head dropping sideways and his breathing heavy. In his lap lay Frodo’s head, drowned deep in sleep; upon his white forehead lay one of Sam’s brown hands, and the other lay softly upon his master’s breast. Peace was in both their faces.
Gollum looked at them. A strange expression passed over his lean hungry face. The gleam faded from his eyes, and they went dim and grey, old and tired. A spasm of pain seemed to twist him, and he turned away, peering back up towards the pass, shaking his head, as if engaged in some interior debate. Then he came back, and slowly putting out a trembling hand, very cautiously he touched Frodo’s knee – but almost the touch was a caress. For a fleeting moment, could one of the sleepers have seen him, they would have thought that they beheld an old weary hobbit, shrunken by the years that had carried him far beyond his time, beyond friends and kin, and the fields and streams of youth, an old starved pitiable thing.