I find it very interesting that Ananda said, "You misunderstand. I'm weeping not for him but for myself, because for all these years I have been constantly at his side but I have still not attained." This is one of the great conundrums of the spiritual path, that we are "seeking" something for ourselves (enlightenment), yet we are told that to be attached to that goal, to desire it, is itself an impediment to our own success.

Perhaps in this case, Ananda had secretly believed that his relationship to the Buddha would be his key to success. So, when the Buddha had passed, he finally gave up hope and "let go" -- and it was in that moment that he finally achieved enlightenment.