19. The Grandfather

Devastated by the recent plot twist in her life, Blair turns her back on her predictable Waldorf existence in favor of a more wild lifestyle, causing Serena and Chuck to have serious concerns about her new lover, Carter Baizen. Vanessa convinces Nate that it may be time to forgive and forget when it comes to his mother's Kennedy -esque family, the Van der Bilts, who abandoned Nate and his mother when they needed them the most. In a misguided effort to be completely honest with each other, Lily and Rufus agree to share lists of their past lovers. Title reference: The 1972 film The Godfather.