A former associate of Chuck’s father, Russell Thorpe – along with his daughter Raina – returns to Manhattan with some unfinished business for our Upper East Siders. Serena and Chuck join forces against Lily. Blair realizes that her mother, Eleanor, may be her key to becoming a future CEO. Nate worries that his father, The Captain, is having a little too much fun and not taking his parole seriously.

Blair is ecstatic to land an internship at W Magazine, but the thrill quickly fades when she finds out that Dan has secured one of the coveted positions as well. Chuck may have finally met his match with Russell Thorpe – and his daughter Raina – back on the Upper East Side. Nate receives alarming news about his father’s business prospects.

Blair enlists Nate’s help to win over her high-strung boss, Epperly, at W Magazine. Damien stirs up more drama on the Upper East Side. Chuck finds himself torn between business and pleasure. Florence and the Machine performs an acoustic version of “Cosmic Love.”

With Russell Thorpe poised for a takeover attempt of Bass Industries, Chuck makes one last-ditch effort to save his family’s company. Blair is given a challenging assignment at W Magazine with the promise of a possible promotion. Serena struggles with her feelings for Ben.

It wouldn’t be a proper Upper East Side party without some major Gossip Girl drama, and for Eric’s 18th birthday celebration there is plenty to go around. Blair decides to speed up the time table on her career path to becoming a powerful woman.... but ultimately stretches herself too thin. Serena is forced to choose between her family and Ben. Chuck and Lily’s relationship remains icy in the aftermath of Lily’s betrayal.

Ben’s mother comes to town, forcing issues to the surface between Ben and Serena. Russell Thorpe is determined to destroy Chuck’s family legacy, but he risks alienating his daughter, Raina, in the process. Billy Baldwin returns as William van der Woodsen, Lily’s ex-husband and Serena and Eric’s father.

As Lily awaits the consequences of her decision, William van der Woodsen, CeCe and Lily’s sister, Carol, come into town to support her and be part of a Taschen photo shoot on “modern royalty” in which the Rhodes family is participating. Unbeknownst to Carol, who has always chosen to keep her daughter Charlie far away from the Upper East Side, Charlie has followed her to New York to meet Serena and the rest of the family. Blair has an epiphany about her future, and grapples with the knowledge of whom she’s destined to be with.

Serena enlists Charlie to go undercover Gossip Girl-style to determine why Dan and Blair are spending so much time together, and what role an unexpected visitor is playing in their lives. With Nate’s help, Raina decides to go on a search for her long-lost mother. Chuck’s hopes about his legacy are dashed with the reveal of devastating information from the past.

Blair’s dreams appear to be coming true, but Serena threatens to jeopardize it all by dredging up Blair’s past. Charlie befriends Vanessa, who may or may not have a hidden agenda. Nate is torn between his relationship with Raina and a truth he must keep hidden out of loyalty to Chuck.

Charlie is finally starting to feel less like a fish-out-of-water with Serena and her friends, but complications present themselves when Charlie is invited to attend the Constance Billard alumni fundraiser. On the road to "happily ever after" Blair finds herself torn between the men in her life. Jack Bass return to the Upper East Side sets off a chain of events that could end up destroying Chuck and those closest to him.

The episode continues from the early events of the Constance Alumni event. Georgina Sparks turns up at the event looking for trouble. Serena and Vanessa reluctantly join forces to find Dan and Charlie, who does not take Dan's rejection of her well. Blair must make a choice between the men in her life when her life is in danger by Russell.