On the anniversary of Bart Bass’ death, Chuck wrestles with an issue from the past and a serious car accident rocks the Upper East Side. Dan and Vanessa attempt to navigate their newly complicated friendship. When Jenny is accused of beating up one of her classmates, Eric is faced with a tough dilemma.

Nate and Serena decide to explore the boundaries of their friendship. Blair suspects that Chuck is having problems forgetting about the woman he saw at his father’s grave. Jenny agrees to accompany Damien to a State Dinner but is unaware that he needs her help with a drug exchange. Vanessa and Dan attempt to move past the awkwardness of Dan’s confession of love. Rufus returns from a ski trip and tries his best to avoid Lily.

Rufus and Lily grow suspect of Jenny’s relationship with Damien. Chuck learns more about the woman who may or may not be his mother. Dan and Vanessa struggle through the awkwardness of dating other people.

Despite being grounded, Jenny continues to see Damien who tells Jenny that he wants to have sex with her. Lily tells Rufus the big secret she has been keeping from him even though she knows it's a huge risk. Dan and Vanessa explore a new stage of their friendship. Chuck is forced to make an extremely difficult decision about his hotel.

Chuck finds himself once again at odds with his uncle, Jack Bass. Eleanor puts Blair in charge of making sure her latest fashion show is a huge success with an important client. Rufus attempts to get Jenny back on track by volunteering to have her help with Eleanor’s fashion show, but the opportunity takes a big turn for the worse when Jenny learns that Agnes will be one of the models.