As season five of Gossip Girl continues, Dair fans get to watch Dan (Penn Badgley) and Blair (Leighton Meester) struggle to consummate their new relationship in episode 518 (“Con Heir”), airing on Monday, April 2. Blair’s ex, Chuck (Ed Westwick), invites his uncle, Jack (Desmond Harrington), to town to thank him for saving his life, but the trip doesn’t go as planned. Meanwhile, Ivy (Kaylee DeFer) finds an unlikely ally in William (Billy Baldwin) in her quest to be accepted on the Upper East Side. Nate (Chace Crawford) is hopeful that a new investor will save his newspaper.
The following week, Elizabeth Hurley makes a return as Diana Payne, who returns to The Spectator to start a power struggle with Nate. Serena, on the other hand, has decided that she’s ready to relinquish the spotlight and sets out to make Lola (guest star Ella Rae Peck) the next “It Girl” of the Upper East Start. Step one? Have Lola model at a Kiki de Montparnasse lingerie show. And Chuck reaches out to Blair about his past in episode 519 (“It Girl, Interrupted”), airing Monday, April 9.