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Things heat up between Serena and Dan when they admit they are in love with each other, despite that they come from polar opposite worlds (she from wealthy Upper East Side Manhattan, and he from working class Brooklyn). But Serena and Dan’s plans to be alone to consummate their romance is interrupted by Vanessa who shows up wanting to spend time with Dan. Meanwhile, Chuck thinks of investing in a strip nightclub to make his father, Bart Bass, proud of him. Jenny discovers a secret that her parents have been keeping from her. Also, Blair is devastated by Nate’s actions when Jenny reveals to Blair that Nate kissed her by accident at the masked ball the night before after he mistook her for Serena. Blair, (being the cynical b*tch she is), tells Jenny they are no longer friends. Nate’s parents think that he should tell Blair he wants to marry her, even though he doesn’t have strong feelings for her. The Archibalds and Waldorf’s have a dinner party celebrating their new business deal together and it’s obvious that Blair is giving Nate the silent treatment. Nate confronts his father about the drugs he found in his house, but he denies having a problem. The two get into a brawl and Nate’s father punches him and as a result Nate turns his own father into the police. Afterwards, Nate gets ready to go see Chuck at the strip club he opened, but Blair stops him and tells him he needs to be with his father. Blair tells Nate that she doesn’t need him and they break up and she heads over to the strip club saying she wants to “escape”, which leads to a sordid tryst between Blair and Chuck in the backseat of his limousine.
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