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Blair is feeling heartbroken and guilty about the current state of her relationship with Nate and her recent indiscretion. However, she manages to put on a happy face for her 17th birthday party and attempts to hide her feelings from her friends. Hoping that Serena and Vanessa can bond, Dan takes Vanessa to Blair’s birthday party, but this ends up making Serena more uncomfortable. Jenny brings her mother home as a surprise, but Rufus isn’t ready to forgive and forget. Finally, Nate’s parents ask him to make a huge sacrifice to save his father’s business as he faces charges of embezzlement and fraud
Serena and Dan finally accept that they are crazy about each other, despite the fact that they come from opposite worlds. Chuck thinks of investing in a club in an attempt to make his father proud of him. Nate confronts his father about the drugs he found in the house, but he denies having a problem. Jenny discovers a secret that her parents have been keeping from her. Finally, Blair is devastated by Nate’s actions when Jenny reveals that Nate kissed her by accident thinking she was Serena
Dan finds himself between two girls when his childhood friend, Vanessa, returns to NY and declares her feelings for him, just as he and Serena are trying to figure out what they mean to each other. At a masked ball, Blair sends Nate on a scavenger hunt, but Nate is distracted by his feelings for Serena. Although Blair said that outsiders were not welcome to the party, a disguised Jenny and Dan sneak into the ball. Finally, Lily asks Rufus to accompany her to an Eleanor Waldorf event only to make Bart Bass jealous
Dan tries to impress Serena on their first official date with an elaborate plan, but fails to understand that Serena is happier with beer than champagne. 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, Lily finds out that Eric is missing from the treatment center, and she finds herself seeking help from her ex-boyfriend, Rufus
Blair gets excited when her mother, Eleanor, chooses her to be the new face of her clothing line. However, Blair’s happiness turns quickly into feelings of betrayal and jealousy when Serena takes her spotlight and Blair finds herself back in Serena’s shadow. Meanwhile, Serena and Dan remember once again that they come from two very different worlds. Also, Nate and Chuck do a boys weekend to blow off steam after Ivy Week ends
As the Upper East Side teens from Constance Billard and St. Jude's prepare for a much-anticipated visit from the Ivy League representatives, Blair (Leighton Meester) uncovers a scandalous secret about Serena (Blake Lively) that may not remain a secret much longer. Dan (Penn Badgley) has his heart and future set on the coveted usher position for the Dartmouth rep, only to be beat out by Nate (Chace Crawford), who has no interest in the school despite pressure from his controlling father, The Captain (Sam Robards).
Meanwhile, Jenny (Taylor Momsen) bonds with Serena's younger brother, Eric (Connor Paolo), and Rufus (Matthew Settle) must swallow his pride and ask Lily (Kelly Rutherford) for a favor to help his son, Dan. Ed Westwick also stars.
J. Miller Tobin directed the episode written by Felicia D. Henderson.
In the wake of the scandalous Kiss on the Lips party, Serena (Blake Lively) receives an icy cold reception from her best friend Blair (Leighton Meester), who reveals that she knows Serena slept with her boyfriend, Nate (Chace Crawford), before mysteriously running off to boarding school.
As if it couldn't get any chillier, Serena decides to take Dan (Penn Badgley) to arch-enemy Chuck's (Ed Westwick) fundraiser brunch at The Palace, and Jenny (Taylor Momsen) seeks advice from Blair, who realizes she may have something to gain by allowing Jenny into her inner circle.
Kelly Rutherford and Matthew Settle also star. Mark Piznarski directed the episode written by executive producers Josh Schwartz & Stephanie Savage.
The privileged prep school teens on Manhattan's Upper East Side first learn that Serena van der Woodsen (Blake Lively, "The Sisterhood of the Traveling Pants") is back in town the way they learn all the important news in their lives -- from the blog of the all-knowing albeit ultra-secretive Gossip Girl.
No one knows Gossip Girl's identity, but everyone in this exclusive and complicated vicious circle relies on her website and text messages for the latest scoop. Even Serena's closest friend, Blair Waldorf (Leighton Meester, "Entourage"), is surprised to find that Serena has suddenly ended her self-imposed exile to boarding school and returned to Manhattan.
Once the Upper East Side's most notorious party girl, Serena's reasons for returning are mysterious, although they may have something to do with her younger brother Eric (Connor Paolo, "Alexander"). Whatever the reasons, the change in Serena is obvious, especially to Blair, whose friendship with Serena has always been competitive and difficult.
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