But merely 10 minutes later in the same episode, Chuck is back at it, this time with Jenny Humphrey (Taylor Momsen), a 14-year-old freshman who happens to be the sister of the guy Serena is on a date with. Still mad about being rejected, Chuck zones in on what he considers easy prey, while Blair, who knows all about Chuck's history with women, eggs him on. He proposes he and Jenny head up to the roof to talk, universal language for: "let me take you somewhere no one will hear you scream," and when she hesitates, offers her some Champagne. Luckily, little J has the presence of mind to text her brother, because two scenes later, Dan Humphrey (Penn Badgley) and Serena barge in on Chuck attempting to pin Jenny against a wall. This second attempted assault ends with Chuck calling Serena a "slut," and threatening to end her life for putting an end to a second non-consensual sexual encounter.