More Dan Stuff
Yes! More ridiculous analysis of Gossip Girl.
I recently re-watched Safran's pet, Bad News Blair. There are so many parts of that episode I find interesting, but one that stands out to me is the conversation between Dan and Rufus regarding Serena and her world, in particular her friendship with Blair Waldorf, ninety-five pound, girly evil extraordinaire. Rufus tells Dan that he has to jump into his relationship with Serena feet first, basically "loosen up and see what happens." Obviously they are talking about Serena, but this really is a great place to start when talking abou the differences in how he handled everything with Serena vs. everything with Blair.
Dan never really did go all in with Serena. I have no doubt that he loved her, but he was never able to see her outside of the image he had built up, without being disappointed. He never really accepted her world or her lifestyle. Even now that Rufus is an honorary VDW, Dan continues to live in a loft in Brooklyn instead of a penthouse in Manhattan. He will not let himself being completely taken in by the UES. Serena is eager to please, so she started trying to be the person he wanted her to be, and that led to deception and the downfall of their relationship, at least in season 1 and 2. At the very end of season 3, he acts a little annoyed that she is running off to spend the summer in Paris, but for the first time in their history, he started to make the leap to jump in and live her way, but was stopped. (Say life is giving you signs... etc). Season 4 is a redux of the same issues: judgement, flightiness, etc.
Then you have Blair. He seems completely willing to jump right in and try to swim. He can take her insults as easily as he can give them (2x18, 4x11), he can see right through wall and offers advice whether wanted or not (1x4, 2x8, 3x18, 4x12), is willing to scheme with her (1x18, 4x11, 4x19), and he is even willing to dress up and go to an UES event that is all about how great the UES is. He doesn't even question the superficiality of the Taschen photoshoot. His mind goes "Blair wants me there? Ok I will be there in 5 minutes." When she goes off to France for the summer, he doesn't at all seem upset. He jokes with her about it and offers his friendship and support. With her, he is willing to jump and see how long he can float, and I am betting on Brooklyn.