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Synopsis: Blair must choose between Chuck and Dan; Nate asks Lola to move in with him; Lily makes an important decision about her marriage and Georgina returns to the Upper East Side.
Season 5 Episode 24 “The Return of the Ring”
Season 5 Episode 23 “The Fugitives”
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Synopsis: Blair enlists Serena to be her stand-in at an important meeting when Blair finds herself needing to be in two places at the same time as Dan seeks to meet with a college rep from Italy for his oversees summer stay in Italy. Meanwhile, Ivy and Lola team up to help Chuck with a personal vendetta against an old enemy of Bart Bass’. Also, Nate makes a decision about the future with Diana Payne.
Season 5 Episode 22 “Raiders of the Lost Art”
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Synopsis: Chuck, Nate, Blair, Serena and Lola team up to uncover what they think is an explosive secret between Diana and Jack. Meanwhile, Dan is offered a prestigious fellowship in Rome for the summer.
Season 5 Episode 21 “Despicable B.”
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Synopsis: Blair devises a plan to regain control over the Upper East Side; Lily throws a Van der Woodsen family gathering with Carol and Will attending; Nate digs into Diana’s past.
Season 5 Episode 20 “Salon of the Dead”
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Synopsis: Blair and Dan throw out a big party for them to come out as a couple; Gossip Girl may ruin Lola’s biggest dream; Serena and Diana have a face-off.
Season 5 Episode 19 “It Girl, Interrupted”
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Synopsis: Serena is determined to turn Lola into the next “it-girl”; Chuck seeks advice from Blair about his past; Diana returns.
Season 5 Episode 18 “Con Heir”
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Synopsis: Chuck wants to express his gratitude to Jack for saving his life. Elsewhere, Blair and Dan’s new romance hits a snag; Ivy gets unexpected assistance from William; and Nate is optimistic about landing a new investor for his newspaper.
Season 5 Episode 17 “The Princess Dowry”
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Synopsis: Blair thinks Cyrus Rose may have found a potential loophole in her pre nuptual agreement to get out of her marriage with Louis. Chuck and Georgina team up in a scheme to destroy Dan’s writing career by revealing that he leaked the video of Blair, but it has an unpredictable outcome. Meanwhile, a family crisis brings William van der Woodsen back to the Upper East Side.
Season 5 Episode 16 “Cross Rhodes”
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Synopsis: Dan feels honored when he learns that Upright Citizen’s Brigade theater troup is performing excerpts from his book, Inside. Meanwhile, Blair tries to prove Serena’s suspicions wrong in order to save their relationship. On her way out of town, Ivy Dickens ends up on a collision course with the Van der Woodsens and destiny.
Season 5 Episode 15 “Crazy, Cupid, Love”
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Synopsis: It’s Valentine’s Day on the Upper East Side and Blair can’t resist playing cupid for someone she loves. Georgina is intent on stirring up more drama and trouble, so she decides to crash Nate’s Valentine’s Day party. Meanwhile, Serena is shocked by something she witnesses at the party.
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