Season 2
Season Two begins with Chuck's quest to try and win back his "true love", Blair Waldorf in the season premiere "Summer, Kind of Wonderful". Blair, however, reeling from the fact that he ditched her at the airport, has hooked up with a handsome, seemingly perfect Georgetown guy by the name of James, originally in an attempt to make Chuck jealous. Even though he immediately sees through her ruse, he is crushed when he spots Blair's heart pin on James's sleeve, and she succeeds. Chuck is suspicious of James and orders a background check on him.
At the posh White Party, Blair makes out with...
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