They clearly love each other, but play a bunch of back-and-forth games and schemes—Blair even enlists Chuck to seduce Vanessa at one point. Nate deals with his family's financial troubles, has an affair with an older, married woman, but then starts dating Vanessa. Lily develops feelings for Rufus, and soon after, Bart conveniently dies in a tragic car accident. ) that she put up for adoption years and years ago. Post-Tripp Serena and Nate start dating, but Jenny sabotages their relationship because she wants Nate. Lily said she was in California visiting her mom, but she really was with her ex-husband, who was treating her for cancer—that turns out to be a fake diagnosis. Georgina shows up and tells Dan she's pregnant with his baby. (Figures.)Nate starts dating a new gal, Juliet Sharp, who prevents Serena from joining a secret sorority and just generally has a bunch of schemes and shady plans.
This will not be the only weird not-incestuous-but-still-creepy love match-up on the show.Sage starts dating Nate, and somehow that is legal. Bart attempts to kill Chuck in a plane crash because Chuck knew too many secrets. They scuffle, and Bart falls off the rooftop of the Empire Hotel, dies. Also, Steven once had a one-night-stand with Lily, and it does not bother Serena that her boyfriend had sex with her mom. Dan teams up with Georgina to write a new tell-all, this time using real names. Dan's in love with Blair, but he wants to make her happy, so he arranges for Chuck and Blair to run away together. A video of Blair confessing her love for Chuck leaks. Lily annuls her marriage to Rufus because she's still technically married to Bart. Serena leaves town, Dan leaves for Rome, and Blair meets up with Chuck in Paris. The car crashes, Blair loses the baby, and Chuck nearly dies. For some reason I've forgotten, Serena and Dan have a fake relationship to protect Blair—but Serena actually falls in love with Dan. The wedding continues, but at the reception Louis reveals he doesn't love her and their marriage is just a contract. Nate unknowingly meets the real Charlie Rhodes—a NYU student. Serena seduces Dan, they have sex, and she videotaped it to get revenge on Blair. Season Six GOSSIP GIRL-- "Gone Maybe Gone" -- image GO601B_ 0220 Pictured (L-R): Penn Badgley as Dan Humphrey, Michelle Trachtenberg as Georgina Sparks, Leighton Meester as Blair Waldorf, Chace Crawford as Nate Archibald and Ed Westwick as Chuck Bass Photo: Giovanni Rufino/The CW -- © 2012 The CW Network. Chuck and Blair make a pact to not be together until they both succeed at their goals—she wants to run her mother's fashion company, he wants revenge on Bart for faking his death and stealing his company back from Chuck.