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New York Magazine labeled Chuck and Blair's relationship as the "Longest-Delayed Breakup" of the season, adding that "the big news was that Blair and Prince Louis are somehow still together and engaged, with the wedding scheduled for November sweeps. We feel comfortable assuming that by then, Chuck will have regrouped enough to break things up ...
In the end, Chuck is escorted by Bart's security to the roof of a building. Minutes later Bart joins him. Blair, alarmed at not being able to locate Chuck, asks around for him and races up to the roof as well. A fight ensues between Chuck and Bart. Blair arrives just in time to see Bart hanging off the side of the building.
After she unites with Chuck and Nate in order to save Serena from the scheming Georgina Sparks, Chuck realizes that his feelings for Blair are real and suggests that they spend the summer together in Tuscany. However, he is discouraged by his father at the last minute, and stands Blair up.
Serena finds Chuck, and discovers his plan to leave Paris under a different identity. Prior to Blair's date with Prince Louis Grimaldi, she visits Harry Winston, when Serena and a French detective arrive, and it is revealed to both Serena and Blair that Chuck had intended to propose to Blair before he was shot.
A former associate of Chuck's late father, Russell Thorpe, along with his crafty and headstrong daughter Raina, return to Manhattan with some unfinished business concerning Bass Industries. Serena and Chuck unite against Lily. Meanwhile, Blair realizes that her mother, Eleanor, may be her key to becoming a future CEO.
Chuck is the resident "bad boy" of the Upper East Side, and like Blair, is both vengeful and manipulative; the two often scheme elaborate plans together. As the show progresses, Chuck develops a softer side, specifically towards Blair, his chief love interest, and Lily, Eric, and Serena, his adoptive mother, brother, and sister.
Louis asks Blair to marry him after she runs away from a royal event Chuck ruined with his drunken declarations of love, though his mother doesn't think Blair is suited to be a princess of Monaco. Later, with the help of Cyrus, Louis' mother is convinced Blair is worthy enough, and in deference Louis often upholds her wishes over Blair's.
Chuck and Blair Waldorf (Leighton Meester) leave the scene and hide from the police as Chuck is considered "a person of interest" in the case. Jack Bass (Desmond Harrington), Chuck's uncle, comes to help him and suggests the two get married since spousal privilege prevents a wife from unwillingly testifying against her husband. Chuck thus ...