Nate and Serena decide to explore the boundaries of their new relationship. Meanwhile, Blair suspects that Chuck is having problems forgetting about the mysterious woman he saw at his father’s grave. Serena asks to accompany Damien to a State Dinner but is unaware that he needs her help with a drug exchange. Things are complicated when Jenny crashes the event and Serena inadvertently acquires Jenny's coat with the contraband stash sewed into it. Elsewhere, Vanessa and Dan attempt to move past the awkwardness of Dan’s confession of love. Also, Rufus returns from a ski trip and tries his best to avoid Lily whom he suspects was unfaithful.
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