Nate and Serena explore the boundaries of their friendship. Blair suspects that Chuck is having problems forgetting about the woman (recurring guest star LAURA HARRING - The Shield, Mulholland Drive, Sunset Beach) he saw at his father's grave. Jenny agrees to help Damien (recurring guest star KEVIN ZEGERS) overcome a challenge he faces. Vanessa and Dan attempt to move past the awkwardness of Dan's confession of love. Rufus returns from a ski trip and tries his best to avoid Lily.