In Season 5, Episode 19: "It Girl, Interrupted," Chuck (Ed Westwick) exhibited a rare moment of vulnerability when he reached out to Blair (Leighton Meester) for advice about finding his mother — despite the fact that her heart is (currently) with Dan (Penn Badgley).

Unfortunately, Blair interpreted this move as yet another way for Chuck to insert himself back into her life. With such a sordid history, we kind of don’t want to blame Blair for assmaking this assumption — but we do! As much as she knows about Chuck, she should know that his relationship (or lack thereof) with his parents is a sensitive issue… But she seemingly handled this topic with the grace of a jackhammer every time she faced him.

So was Blair being too harsh on Chuck? Or was she being appropriately cautious, considering their history? Can they really never be friends if they can’t be lovers?

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