Episode 16: Cross Rhodes
Dan feels honored when he learns that Upright Citizen's Brigade is performing excerpts from his book, Inside. Blair tries to prove Serena's suspicions wrong in order to save their friendship. On her way out of town, Ivy ends up on a collision course with the van der Woodsens.
Episode 17: The Princess Dowry
Blair thinks Cyrus may have found a potential loophole in her prenup. Chuck and Georgina partner up in a scheme, but it has an unpredictable outcome. Meanwhile, a family crisis brings William van der Woodsen back to the Upper East Side.
Episode 18: Con-Heir
Chuck invites Jack to town to thank him for saving his life, but finds the trip doesn't go exactly as planned. Blair and Dan attempt to consummate their new relationship -- but unexpected roadblocks get in their way. Meanwhile, Ivy finds an unlikely ally in William in her quest to be accepted on the Upper East Side, and Nate is hopeful a new investor will save his newspaper.
Episode 19: It Girl, Interrupted
Serena decides she is ready to relinquish the spotlight and sets out to make a reluctant Lola the next "It Girl" of the Upper East Side, starting with modeling at a Kiki de Montparnasse lingerie show. Meanwhile, Chuck reaches out to Blair for advice about his past, and Diana Payne's return to The Spectator starts a power struggle with Nate.
Episode 20: Salon of the Dead
To celebrate their official coming out as a couple, Blair and Dan host a glamorous British-themed Salon, including guests Julian Tepper and Jenna Gribbon (founders of The Oracle Club). Lola lands the audition of a lifetime, but Gossip Girl may have other plans for the Upper East Side's latest It Girl. Meanwhile, Lily and Rufus disagree over the best way to handle the Ivy situation, and Serena and Diana face-off over secrets they both would prefer remain secrets.
Episode 21: Despicable B
Blair feels like her Upper East Side status might be slipping away and devises a plan to assure that doesn't happen. Meanwhile, Lily throws a family gathering - including William, Carol and Lola - in an attempt to prove the van der Woodsen family is as united as ever. Finally, Nate digs into Diana's past and is surprised by what he discovers.
Episode 22: Raiders of the Lost Art
Diana and Jack may be harboring another secret, and Chuck and his pals want to unearth the details. Meanwhile, Dan gets the opportunity to spend the summer in Rome on a fellowship.
Episode 23: The Fugitives
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. Meanwhile, Ivy and Lola team up to help Chuck with a personal vendetta, and Nate makes a decision about the future with Diana Payne.
Episode 24: The Return of the Ring
When Gossip Girl goes after Blair as she's never done before, Serena admits she may have unintentionally played an important role in Blair's latest nightmare. Meanwhile, Nate invites Lola to move in with him, and Lily must make a big decision about the future of her marriage. Finally, by episode's end, Blair will make a choice between the two men in her life; will it be Chuck or will it be Dan?
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