Actually Chuck is the richest of all of them. Sorry just had to correct that, haha. Chuck is the richest, Serena would be next because her mother is a Rhodes/Van Der Woodson/Bass and has money/businesses from each of those marriages PLUS her own familys money. And after Serena would be Blair (I think, either Blair or Nate)
Which serena blairmade him ending up with Serena seem like he was settling because he couldn’t have Blair, which is really quite sad for Serena. I do think he loved Serena, but it was an immature high school love. And one that was outshined once he fell for Blair. I mean, Serena told him she loved him at Blair’s wedding and Dan could not have cared less.
Blair took care of Serena when she was drinking heavily, doing drugs, and sleeping around in their youth, and Serena helped Blair through her eating disorder. Blair provided a sense of stability and home during Lilys various marriages and boyfriends. The toxicity didnt seem to start until Nate and Serena began flirting with each other.
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