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To be honest none of the characters should be together. All their relationships are unhealthy. But it's not real life, it's a tv show and they're not exactly gonna have all their characters pair off with random guest stars. So in my opinion that doesn't really matter that much. But even if that did matter, I think DS should be together as they would be better versions of themselves, or at least that's how i see it playing out in my head
I think he would stop being so much of a dick if he and Serena finally reconciled for good. He'd have to accept the UES and stop having this oversized opinion of himself just because he's not from their world