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I guess I was always looking for something that uniquely defined these two and they didn't give us a whole lot which is sad.
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They shared quite a bit in common, but it was hard to see anything that was uniquely theirs. They didn't immediately turn to one another when they had a problem -- Serena went to Blair with her murder issue, Chuck went to Nate when he was hurt -- and much of their bonding was over by the end of S1-S2. I would have loved to see more explicitly written. On the other hand, I would have hated to see them slide into a romantic relationship given the pilot and their mutual relationships with Blair.