10. Riding in Town Cars with Boys

Complete story — includes the ending

Serena and Lily prepare Charlie for her first debutante ball to welcome her into New York high society, but the vindictive Max is determined to reveal Charlie/Ivy's secret by any means necessary. Meanwhile, Blair must choose where she stands with both Louis and Chuck as she hides out at the Humphrey loft in Brooklyn from the press. Dan realizes that it is time to tell Blair the truth about his feelings for her. Louis returns to New York where he meets with Serena and confides in her about his fears about his future with Blair. Nate learns that his grandfather, William van der Bilt, owns the majority of stock shares at The Spectator and he influenced Diana to hire him. William invites Nate to an upstate retreat, but Nate's cousin, Tripp, has been excluded. After Dan sacrifices his own love for Blair for her happiness, Chuck and Blair are hurried into a car from Charlie's debutante ball. Their car is tailed by vicious paparazzi (Charlie sent a blast to Gossip Girl and tipped them off in order to keep them away from her) who cause them to crash, leaving Chuck fighting for his life and the pregnant Blair fighting to keep her baby. After Max's pleas to both Serena and Nate about Charlie's real identity fall on deaf ears, he runs into Tripp van der Bilt, whom he tells Ivy’s story to. Charlie calls Carol Rhodes to tell her that she is leaving New York City after she tells Rufus that she is a fraud. Also, Diana is called by Jack Bass and informed about Chuck and Blair's car accident; she is somehow involved. Title reference: The 2001 film Riding in Cars with Boys.