Original Air Date: 24 October 2007
Dan is torn between two girls when his childhood friend, Vanessa, returns home and declares her feelings for him, just as he and Serena are trying to figure out what they mean to each other. At the infamous masked ball, Blair sends Nate on a scavenger hunt, but Nate is ultimately still distracted by his feelings for Serena. Although Blair makes it perfectly clear that outsiders are not welcome, a disguised Jenny and Dan sneak into the ball. Elsewhere, Lily asks Rufus to accompany her to an Eleanor Waldorf event in order to make Bart Bass jealous.

Original Air Date: 16 October 2007
Dan makes elaborate plans to impress Serena on their first official date. That same night, Jenny is invited to the infamous Blair Waldorf sleepover and finds herself in a high stakes game of “truth or dare.” Meanwhile, when Lily discovers that Eric is missing from his treatment center, she finds herself seeking help from her ex-boyfriend, Rufus.

Original Air Date: 9 October 2007
Blair is thrilled when her mother, Eleanor, chooses her to be the new face of her clothing line. However, Blair’s happiness soon turns to feelings of betrayal and jealousy when Serena moves into the spotlight and Blair finds herself back in Serena’s shadow. Meanwhile, Serena and Dan are reminded once again that they come from two very different worlds, and Nate and Chuck indulge in a boys’ weekend to blow off steam after Ivy Week.

Original Air Date: 3 October 2007
‘Gossip Girl’ narrates Ivy League week as the teens on the Upper East Side schools of Constance Billard, and the rival St. Jude’s, prepare for a much-anticipated visit from the Ivy League representatives. Blair uncovers a scandalous secret about Serena that may not remain a secret much longer. Dan has his heart and future set on the coveted usher position for the Dartmouth rep, only to be beat out by the snobbish Nate, who has no interest in the school despite pressure from his controlling father, The Captain. Meanwhile, Jenny bonds with Serena’s younger brother, Eric, and Rufus must swallow his pride and ask Lily for a favor to help his son, Dan.