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Is it at all possible that Glorfindel volunteered to return to Middle-earth? Maybe Ecthelion simply wanted to "enjoy his retirement" as it were - we have to assume that, in the fulness of time, he was re-embodied in Aman and got to go about his business.
What with no Elves ever permanently dying (except Fėanor I suppose, and however the Finwė-Mķriel tradeoff ended up working out, and perhaps some others - I always liked that line which might be in Morgoth's Ring about the reports of resurrected Eldar about the fėa of the Avari in Mandos) it must have become really crowded in Aman after a while. I know the Eldar did not reproduce as quickly as Men but still...
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"Since the evening of that day we have journeyed from the shadow of Tol Brandir."
"On foot?" cried Éomer.
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