Behold the very first Rory Gilmore hater.

Headmaster Hamlin Charlseton

Okay, maybe hater is a bit of a strong word – but it was clear from his first appearance that Headmaster Charlseton was not here to cater to the whims of a spoiled New England Teenager. He was here to run his prestigious prep school, and if Rory couldn’t keep up with the expected work load that was her problem. In the revival he’s somewhat softened towards her – although that could be because he’s no longer speaking with a current student of his school, who he’s trying to push towards excellence, but rather an adult who might need a helping hand from a friend of her family. Although even taking that into account, it’s a pretty generous offer he extends to her. To teach at his school at any position she wants, and all she would have to do is go back to school and get her Masters first. Makes it all the more galling when Rory turns her ugly little nose up at it, and dares to complain to poor Jess about how it proves she’s got the stink of failure around her. Yeah, you do Rory – maybe you want to stop complaining and do something about that.

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