Season synopsis
Contains spoilers for this season and earlier seasons.
With high school over, Serena, Blair, Nate, Chuck, Dan and Vanessa move into college and adult life while Jenny rules Constance as its new Queen Bee. Serena defers Brown and stays in Manhattan; she begins dating Nate, while Dan and Vanessa try to make their friendship into a relationship. Chuck buys the Empire Hotel and pursues a life with Blair, but their new partnership falters when they discover that honesty is harder than their old games. Serena’s father William returns and hides the truth about Lily’s illness.
Chuck’s uncle Jack offers Blair the hotel if she sleeps with him, then reveals that Chuck arranged the bargain. Blair ends the relationship. Meanwhile, Jenny’s attempts to control Constance strain her ties with Eric and Rufus, and her pursuit of Nate brings her into conflict with Serena. She circulates a picture that makes it look as if Dan and Serena slept together. They admit they shared a kiss, complicating their relationships with Nate and Vanessa.
In the finale, Blair is delayed at the hospital when Dorota gives birth and misses Chuck’s Empire State Building meeting; Chuck, believing she has stood him up, sleeps with a distressed Jenny. Blair reaches him afterward and he is about to propose, but Dan exposes what happened. Blair rejects Chuck and banishes Jenny to Hudson. Serena and Blair leave for Paris, while Dan is interrupted from following them by Georgina’s news that she is pregnant. In Prague, muggers take Chuck’s ring and shoot him as he tries to protect it; the season ends on his apparent death, without confirming that he has died.