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So Dan and Serena get back together at the start of season two, but Dan really wants to keep it a secret.
Serena persuades him that they should reveal all at Blair’s upcoming party … Lily and Rufus’s love child was all-around one of the show’s worst storylines, and it led to one of the most egregious "Dan as Gossip Girl" fails.
Once again, Dan is stunned by a Gossip Girl update that reveals Georgina’s chillin’ on a beach while he’s taking care of her baby. Serena wakes up in a seedy hotel room after an overdose, and Dan is the only person who believes her when she says she’s been framed. That conversation happened about five minutes earlier, so unless Dan did some incredibly speedy typing and auto-publish scheduling, he must have a Gossip Girl intern doing the posting for him.That’s not the story Dan is visibly surprised to read a Gossip Girl update saying that Serena’s looking for a date to the masked ball, and decides to blow off his plans with Vanessa to go and surprise her. The exposed brick doesn’t care that you’re Gossip Girl.Side note: This is also the episode where Vanessa comes back to town and gets all self-righteous about her former hipster bae Dan now being into the Upper East Side scene. ” she yells, after finding out he snuck into the masked ball. Talk about doing the nasty, or should I say being nasty? On one level, you have to respect Dan’s commitment to the Gossip Girl persona here.Chuck Bass is the Casanova bad boy, Nate's bff who finds himself falling in love with his best friend's girl.Serena is a former bad girl, and Blair's mortal enemy/bff while Dan is struggling to merely get accepted into a prestigious college, owing to the fact that his family doesn't have much money.