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Episode 2.09: There Might Be Blood
Airdate: November 3, 2008

Blair "babysits" teenager Emma who wants to hit the top five clubs according to Gossip Girl and hopes to lose her viriginity before another student does. Emma blackmails Blair into helping her or she'll tell her mother that Blair was the one who took Emma to clubs and got her drunk. Since Emma's mother can help Blair get into Yale, she complies... A few beautiful foreign girls get a bit too cozy with Aaron, which will make Serena jealous. The New York Philanthropic Society honors Lily and Bart Bass. Chuck and Rufus also appear.
Serena invites Aaron (guest star John Patrick Amedori) to be her guest at a charity gala honoring Lily and Bart, but after discovering a secret that Aaron has been keeping from her, she begins to question whether Aaron is the guy she thought he was. Hoping it will help her chances of getting into Yale, Blair naively agrees to babysit the 15-year-old daughter of a prominent Yale donor, but the teenager proves to be more than a handful and Blair begins to suspect that the evening may actually wind up hurting her chances of getting into the college of her dreams. Meanwhile, Jenny and Agnes (guest star Willa Holland) plan a guerilla fashion show that will either launch Jenny's star or ruin her chances of ever being accepted by the industry. Penn Badgley, Chace Crawford, Ed Westwick, Jessica Szohr and Matthew Settle also star.
Actress and NYC fashionista Stella Maeve, has joined the cast of Gossip Girl , the TV Fanatic can exclusively reveal. Stella plays Emma, the young teen daughter of a Yale University alum, who Blair gets to "babysit" for the evening. Does Miss Waldorf need a side gig? Emma's been doing her homework on her socialite nanny by reading up on Gossip Girl, and has some interesting ideas on how she wants to be entertained by Blair.