Season 5
The season began in Los Angeles when a re-energized Chuck and Nate decided to pay Serena a visit. Chuck has a newfound philosophy and says "yes" to everything, even death defying stunts. Serena continues to work on the movie set, and is offered a full-time job at the end of the episode. Nate begins an affair with an older woman, Diana Payne, who may have an ulterior motive for being with Nate. Back in New York, Dan learns that Vanessa has published one chapter of his novel, and Blair continues to plan her wedding to Louis, and she also learns she is pregnant. After realizing she still had feelings for Chuck, Blair and Chuck decide to go away together, but their car crashes. As a result of the crash Blair loses her baby, Chuck nearly dies, and Blair eventually marries Louis. The season also focuses on Nate running an online gossip site NYSpectator, Blair and Dan's friendship turning into a relationship, Chuck's quest to find his real parents which leads him to discover that his father, Bart, is still alive, and the effects of CeCe's death on Lily and her marriage to Rufus. At the end of the season, Blair makes a choice between Dan and Chuck, and Lily makes a choice between Rufus and Bart. Serena is seen leaving town while Dan decides to write a new book about the Upper East Side, with the help of Georgina.
Episodes
1 Yes, Then Zero Sep 26, 2011 
2 Beauty and the Feast Oct 3, 2011 
3 The Jewel of Denial Oct 10, 2011 
4 Memoirs of an Invisible Dan Oct 17, 2011 
5 The Fasting and the Furious Oct 24, 2011 
6 I Am Number Nine Nov 7, 2011 
7 The Big Sleep No More Nov 14, 2011 
8 All the Pretty Sources Nov 21, 2011 
9 Rhodes to Perdition Nov 28, 2011 
10 Riding in Town Cars with Boys Dec 5, 2011 
11 The End of the Affair? Jan 16, 2012 
12 Father and the Bride Jan 23, 2012 
13 G.G. Jan 30, 2012 
14 The Backup Dan Feb 6, 2012 
15 Crazy, Cupid, Love Feb 13, 2012 
16 Cross Rhodes Feb 20, 2012 
17 The Princess Dowry Feb 27, 2012 
18 Con-Heir Apr 2, 2012 
19 It Girl, Interrupted Apr 9, 2012 
20 Salon of the Dead Apr 16, 2012 
21 Despicable B Apr 23, 2012 
22 Raiders of the Lost Art Apr 30, 2012 
23 The Fugitives May 7, 2012 
24 The Return of the Ring May 14, 2012