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There are no hints, only coincidences. They pulled the reveal out their ass.
Serena wakes up on the train in 2007 and realises that she's been dreaming up this terrible, terrible show.
Serenate: the most screwed over ship on this series. They waited way too long to bring these two together (should've happened in season 2) and then Serena screws him over (Dan too) by playing with his heart (late season 3/early season 4). But I guess they were too good looking to be allowed...