Original Air Date: 9 January 2008
The shadowy and unseen ‘Gossip Girl’ takes pleasure in reporting that Serena was spotted by one of GG’s Web contacts buying pregnancy tests at a local pharmacy. Of course, on the Upper East Side, the truth is often even juicier and more scandalous than the gossip when Dan’s sister, Jenny, learns that Serena was purchasing the tests for Blair who fears she might be pregnant from her trysts with Nate. But things get worse when Nate finds out that Chuck has been having an affair with Blair and both nearly come to physical blows, and Blair becomes ostracized by the rest of her clique as her reputation of a slut becomes more known. Meanwhile, Rufus, in an attempt to cheer himself up following his breakup with Lily, goes on a date with his art gallery sponsor, Bex, to a local bar.

Original Air Date: 2 January 2008
Serena, Blair, Nate, Chuck and their entourage break into the school swimming pool for a night of fun, but when a member of their group nearly drowns, the school threatens to expel the person responsible for the break-in. Everyone agrees to keep a secret pact and say nothing, but it ultimately creates major tension between Serena and Dan, who isn’t sure he’s ready to take the fall for someone else and risk his future. Meanwhile, Vanessa is working on a documentary project about private schools and accidentally captures Blair and Chuck discussing their affair. Also, Lily contemplates telling Rufus how she really feels about him.