Con Heir (S05E18)

Chuck invites Jack (recurring guest star Dedsmond Harrington) 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 (recurring guest star Billy Baldwin) in her quest to be accepted on the Upper East Side, and Nate is hopeful a new investor will save his newspaper. (Warner Bros. UK)