Blair Waldorf and Chuck bajo come from the same social circles and appear to have known each other from a very young age. Blair's current boyfriend, Nate Archibald is also Chuck's best friend, throwing the two even closer in the same clique.

In the first two episodes Blair doesn't appear to have any of the hostile feelings towards Chuck which many others do, and infact the pair are shown to be having a good time in each others company (see:limo). In their brief scenes together they appear to share a chemistry like no other (atleast we think so) and this can only spell good things for their future.