I think it's the later considering that the Great Gatsby ends in tragedy and the whole novel is a deconstruction of the American Myth of the Self-Made Man. That's putting it lightly. Pokémon is a more optimistic take on the world.
I don't think it's that. Ash has many friends before and after, just like Serena in her journey in Hoenn. The bittersweet is more of the fact they just happen to encounter each other at the very last moment. You can tell that they would love to talk about their past adventures and ask each other...
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