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Blair and Chuck
Do not send angry letters about this. I know that everyone loves Chuck and Blair, and to say negative things about these two amounts to sheer blasphemy. But hear me out.
For one, Chuck is not a good person. We watch him attempt to rape not one, but two women, (including Serena) in the very first episode. He’s smarmy, sleazy, and all the ascots and limos in the world can’t change that smug swagger. He’s universally despised because he treats everyone like they are beneath him
He seemed to soften a little when his feelings for Blair developed, but not enough to change him into a whole new human. He offered Blair (and her sex) up to his uncle in exchange for a hotel, which seems a little out of character since he perceives her as “his” and often reduces her to nothing but a possession.
He’s emotionally abusive, often threatening her, yelling at her, and performing violent outbursts when she doesn’t perform like she wants. This doesn’t mean Blair is an angel. She gives Chuck a run for his manipulative money. She lies, steals, and cheats, and does everything (stopping short at rape) to get what she wants.
Some folks would argue that they deserve each other, but nobody deserves either one of these two.