Feeling pressured, Nate confesses what his mother wants him to do to Chuck, who uses that information to ruin Blair's interest in winning him back.
Meanwhile, Nate's mother Anne Archibald tries to convince him to get back together with Blair to secure Eleanor's support in their recent legal battles regarding Howard Archibald's embezzlement. To remind herself of this, she disinvites Chuck from her birthday party before going to the jewelry store to pick out gifts for others to pick up. On her seventeenth birthday, Blair realizes how much she misses Nate and wants him back. At the end of the night, he takes Blair home in his limo and she ends up losing her virginity to him in the backseat. While there, Chuck dares her to get onstage and she surprises him by going up and dancing. As a result, she breaks up with him and heads to the club, Victrola, to escape her troubles with Chuck. Meanwhile, Blair learns from Jenny Humphrey that Nate mistook her for Serena and confessed that he still has feelings for her. However, Bart doesn't like the place and shames Chuck for looking for more ways to be around strippers and parties. In Victor Victrola, Chuck invites Blair to come see the club he's trying to convince Bart to buy, and she's impressed with the place. She uses the information to out Serena as a drug addict during the mixer, but later learns it was Eric who was there. Chuck takes photos and shows them to Blair, who is pleased with what he found. He follows Serena and sees her entering The Ostroff Center, a rehab facility where, unknown to Chuck and Blair, her brother Eric van der Woodsen is staying. She explains that she needs answers on why she returned to New York, and Chuck is willing to help her get them. After her fight with Serena turns physical, Blair calls Chuck for help in getting revenge. Jude's throws a mixer for representatives of Ivy League colleges. In Poison Ivy, the junior class of Constance Billard/ St. Later, they both take part in informing Dan about Serena's indiscretions with Nate. Blair vents to Chuck, who offers to help by giving her the key to his suite to finally have sex with Nate. The two showing up at the brunch angers Chuck and Blair, due to the fact that Serena slept with Nate and the fact that Dan punched Chuck at the Kiss on the Lips Party.
They appear to be having a friendly, good time before Serena and Dan arrive. Shortly after, in The Wild Brunch, Chuck's father Bart Bass hosts his annual brunch for his foundation and Blair and Chuck sit together along with Nate, Isabel Coates, and Kati Farkas. At the end of the episode, the two share a comrade-like moment. It is obvious that at this point in time, neither Blair nor Chuck have any romantic feelings toward each other.
Throughout the episode, Chuck talks openly to Nate about how he should seal the deal with Blair. In Pilot, Chuck and Blair appear to have an acquaintance-like friendship.
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