- Serena and Dan finally acknowledge they are crazy about each other; Jenny discovers a secret about her parents; Blair is once again devastated by Nate's actions.
- 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. 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 when he thought Jenny was Serena at the masked ball the night before while Jenny was wearing Serena's mask. Blair, completely shattered by the news takes it out on Jenny, by telling her they are no longer friends. The Archibalds and Waldorf's have a dinner party celebrating their new business deal together and it's obvious that (a) Nates parents are pressuring Nate into saying he will want to marry Blair, even though Nate isn't even though Nate isn't even sure he loves Blair anymore and (b) 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 outside and Nate's father punches him which attracts the attention of the police. Nate says he wants to press charges. Nate finds out that the Captain's bail is set at 1 million dollars as the police have discovered the Captain has been embezzling from work. 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 the beginning of the relationship between Blair and Chuck in the backseat of his limousine.
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