Chuck’s continued investigation into his father’s dealings leads him to an unlikely event with Manhattan’s elite, where he hopes to find the one person who can tell him the truth about Bart. Serena and Steven decide to reveal their romantic histories so they aren’t surprised by anything, but neither was prepared for what they uncovered. With The Spectator in jeopardy after Dan decided to publish elsewhere, Nate must make a difficult decision to keep it in business. Meanwhile, Georgina pushes Dan to choose a worthy person to date to boost his image, but he finds himself drawn in a different direction.

After a run-in with an increasingly paranoid Bart, Blair grows alarmingly concerned for Chuck’s safety. However, feeling confident that his father will never hurt him, Chuck makes a deal that could change his life. Wanting to make things better for Chuck, Blair devises a plan with the help of Serena, Georgina and Sage to try and get what they need out of Bart. Meanwhile, Nate's financial dilemma finally lands him in a place that he never thought he would be.