From season one, the witty duo shared a connection that (verrry) slowly and realistically evolved over the seasons, leading to a real friendship and eventual romance late in the series. Chuck and Blair fans were, to put it mildly, about to light the Internet on fire over the relationship.
Fling or Endgame: Sadly, Dair didn't stand a chance in the face of Chair. Chuck and Blair ended up married, as did Dan and Serena…after he was revealed to be Gossip Girl. We know. WE KNOW.