(Season 4 episode 8) Chuck and Blair have been secretly sleeping together. 38. Gossip Girl (2007–2012) Error: please try again. Chuck hosts a “Saints and Sinners” masquerade party at the Empire Hotel. At the party, Dan and Nate don’t know what to make of Serena’s strange behavior and mixed messages. Blair sets her See full summary »
Blair and Chuck adjust to their new status as a couple; Serena returns from Europe with many secrets and a complicated relationship with Carter. (Season 3 episode 1) Chuck and Blair are madly in love.
After the events in Inglourious Bassterds, Chuck and Blair ultimately split up in The Unblairable Lightness of Being. Throughout seasons four and five, the two go back and forth with their relationship. In the season five finale The Return of the Ring, Blair chooses to be with Chuck and they make a pact to ensure they end up together.
With Serena’s reputation on the line, Blair takes matters into her own hands to deal with manipulative Georgina. (Season 1 episode 18) Blair and Chuck reconcile. 9.
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