Departure (2019)

S02E19 The Grandfather

Feeling shattered by her current circumstances, Blair chooses to embrace a reckless lifestyle, straying from her ideal Waldorf image, which worries both Chuck and Serena. Meanwhile, Vanessa urges Nate to let go of the past, especially after his mother's family, the Vanderbilts, turned their backs on both of them. In an effort to be candid with one another, Lily and Rufus compile lists detailing their previous romantic entanglements.