Eleanor Waldorf's upcoming nuptials threatens to overshadow Blair's birthday. College interviews bring out the best and worst in the seniors, as Blair hangs out with her new stepbrother-to-be Aaron Rose, and Dan finds out how just not into him Serena is. Nate starts hanging out with Jenny. Serena and Blair reunite as best friends again.
You Know You Love Me picks up at the start of senior year. Blair is anticipating being deflowered by Nate. Outsider Dan is in love with the beautiful, yet shallow Serena. When they're not busy wearing the right clothes and being seen at the right places, the cast prepares for college admission interviews at the most prestigious institutions. This second series installment moves toward the impending nuptials of Blair's mother and her dreadful fiancée. Blair pouts because she's not the center of attention. Nate falls for a younger (and more common) freshman. Dan is blinded by obsession and Serena is oblivious to everything that's not in her best interest. It's just business as usual for Gossip Girl's teenage royalty.