I think you are looking at things the wrong way round, Wildespace. It is easy to look at the short, sickly lives of Men to be a curse compared to the long spans given to the Elves. In fact the Gift of Illuvatar was eventually seen by the Numenorians as the Curse of Men because they had lost sight of what the Gift was. Elves are tied to Ea. They have long lives and remain young, but when Ea finally ceases to be, so do they. Men on the other hand, while possessing only short lives on Ea, and a long wait in the Halls of the Dead, get to join Illuvatar following the End of Ea. In a sense, therefore, Men get to go to Heaven for eternity, while Elves only get the relatively shorter existence within the confines of Ea. In the short-term Elves seem to get the better deal, but in the long-term it was Men who had the greater gift.
They have long lives and remain young, but when Ea finally ceases to be, so do they. Men on the other hand, (...) therefore, Men get to go to Heaven for eternity, while Elves only get the relatively shorter existence within the confines of Ea.
But the Elves do not cease to exist at the End of Arda... or that is to say, they no more necessarily cease to exist than Men do when they die.
Part of the 'gift' was the release from Time -- which I guess is at least part of the meaning behind the name The Lay of Leithian or 'the lay of the release from bondage', a poetic work in which the Elf Luthien escapes deathlessness.
Agreed Ithilien and Brego.
And lastly there is the oldest and deepest desire, the Great Escape: the Escape from Death. Fairy-stories provide many examples and modes of this — which might be called the genuine escapist, or (I would say) fugitive spirit. (...) Fairy-stories are made by men not by fairies. The Human-stories of the elves are doubtless full of the Escape from Deathlessness. But our stories cannot be expected always to rise above our common level. They often do. Few lessons are taught more clearly in them than the burden of that kind of immortality, or rather endless serial living, to which the “fugitive” would fly. For the fairy-story is specially apt to teach such things, of old and still today.
JRRT, On Fairy Stories
I would especially note Tolkien's: 'The Human-stories of the elves are doubtless full of the Escape from Deathlessness.'
Immortality a blessing? well, it depends... If we look to both sides of the gift. In one hand Elves have the possibility of last forever, learn tons of things along all those years, epoques, etc. and get wiser as the years pass through, enjoy the chance of seeing how things develop -for best or worst paths-, share the life of Ea and feel that they are a part of it, suffering its harms and caring it as it must remain pure and let's say, healthy. On the other side, we have to take into account that even a mortal life is a big burden sometimes. Men have a shorter life but all the events that happen during those years, can be happy or terrible. When I see the battles against Mordor and the cruelties that some of them suffer, wow, I can say that I rather prefer death to pain.
Elves longlives brings them the chance to possess a great wisdom, and in my opinion, the wisest thing is not to judge; to think that everything that happens is due to a higher power out of hand from any Ea's living being. Anyway, to be wise is very hard when you are kind-hearted as the Elves are. Indeed, the way I would describe the Elves as the eyes of an old person: they show joy for the current moment they live but hide the melancholy of those forgotten harder days of the past; as if they live now trying to be thankful for these quiet days but never let past sufferings in the house of oblivion.
I say it's about equal.
Elves weary of Middle-Earth could just run off to Valinor (which is free from Morgoth's marring of Arda) and live blissful lives until the End of Time. Even after the destruction of Arda, it is likely the Elven feä would be taken into Eru's Halls as well rather than be dissolved into nothingness.
Elros - I think it's most likely that he was very much like his father Eärendil in terms of his spirit/mind - opposed to his mother Elwing and twin Elrond.
Elwing chose to be one of the Elves. Eärendil would have rather been one of the Men; however, for the sake of his wife, he chose to be one of the Elves.
... and perhaps there was no 'Elwing' in his life, to make him choose otherwise and he just did as his father would have, had he not resolved to follow his wife in her choice.
But then again, perhaps there was a woman of the Race of Men who inspired his choice. Though I would have thought there would have been some mention of it, if that had been the case.
Immortality - is vastly overrated. It's said also that Elves and even some of the Valar envy the Gift granted to Men, that they can escape the weariness/sorrow they are doomed to endure.
Personally, it's not something I'd covet for myself. Life can be tiresome enough as it is, in one lifetime - I can't imagine how horrific it would be to watch history repeat itself with one pointless war after another until the end of time.
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