This is one of the great conundrums of the book for me, Child.
Frodo may be a sheltered creature, but he is certainly not that naive when it comes to the logistics of traveling in the wilds of Middle-Earth. Anyone from a time when all travel had to be done by foot or horseback would understand the advantages of traveling in the summer months. Milder weather, food would be more plentiful, rivers would be lower and more passable. Even our own car-crazy culture prefers traveling in summer to winter!
So why did he delay? We may be viewing the situation with 20-20 hindsight. We know that Frodo is in for a very long, dangerous journey to the very end, but at the beginning of the chapter "Three is Company", even Gandalf seems to be uncertain just how involved Frodo will be with the fate of the Ring, despite his earlier, dire warnings. He cannot even suggest a direction that Frodo might take, and implies that perhaps Frodo will be able to pass the burden of the Ring to others.
Perhaps Gandalf's ambiguity gave Frodo a false sense that the situation was not so urgent as it really was. Plus we have to remember Gandalf's promise to return and accompany Frodo and Sam on the trek. You really can't blame Frodo for waiting the arrival of as powerful a traveling companion as Gandalf before starting his journey.
But I have a feeling the real reason Frodo hesitated was that he was very aware, deep in his heart, that he and the Ring would see the journey through to the very end. There would be no other to step in and relieve him of the responsibility. And as on Amon Hen, Frodo was simply afraid.
Being a procrastinator myself, I can understand choosing a signifcant event to use as a goad to push you into facing an unpleasant task. As long as Frodo promised himself that he would start his quest after Bilbo's birthday, he could bury all his fears and dread in the background for a time, and enjoy one last summer in his beloved Shire. But when the anniverary date came, he kept his promise and set out, firmly believing that he would never survive to return home again.
It may have not been the most heroic way to handle the situation, but for Frodo, it worked.
[ August 21, 2002: Message edited by: Birdland ]
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