In the fifth-season finale, Blair makes a choice between Chuck and Dan. Meanwhile, Lily comes to a decision about her marriage; and Nate suggests that he and Lola move in together.
A busy Blair asks Serena to impersonate her at a meeting. Elsewhere, Ivy and Lola join forces to help Chuck exact revenge; and Nate makes a choice regarding his future.
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
Blair plots to ensure her social status remains intact, while Lily tries to solidify her family by hosting a gathering for them. Elsewhere, Nate looks into Diana’s background and unearths a surprise.
Blair and Dan go public as a couple by hosting a salon. Meanwhile, Lola gets to audition for a coveted role; Lily and Rufus clash over how to deal with Ivy; and Serena and Diana have a confrontation about secrets they don’t want divulged
Serena wants to pass her It-Girl torch to a hesitant Lola, whom she pressures to do a modeling gig at a lingerie show. Elsewhere, Chuck seeks Blair’s guidance regarding his past; and Diana resurfaces and stirs things up at Nate’s newspaper.
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
Blair believes there’s a possible loophole in her prenup. Meanwhile, Chuck conspires with Georgina on a scheme; and William returns to support his family in a crisis
Dan discovers that a comedy group is performing excerpts from his book. Elsewhere, Blair attempts to salvage her friendship with Serena; and Ivy runs into the van der Woodsens as she heads out of town.
Nate hosts a Valentine’s Day party, which Georgina crashes. Meanwhile, Blair tries her hand at matchmaking; and Serena is startled by something she observes