In the episode "O Brother, Where Bart Thou?", Chuck is devastated by news of his father's death, prompting Blair to offer her support while telling Chuck that she loves him. He initially shuns her advances, but later turns to her for comfort. However, the two stop seeing each other due to Chuck's uncle, Jack Bass, convincing him he has an inability to commit to a relationship. After being rejected by Yale, Blair finds unexpected encouragement from Nate. She is later accepted into New York University, and her competitive relationship with Georgina is eventually renewed.