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No, the classes are not Harkness based, but Humanities classes do use the roundtable method. I’d say that grading really depends on the individual teacher.
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You can participate in 1 Signature Program over your Choate career or two if you include Term Abroad. (You could do ARC and Term Abroad, but not ARC and JFK.)
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You can’t really ask to switch a roommate as far as I know, but if it’s an identity issue (homophobia, racism, xenophobia, etc) I’m sure there are accommodations.
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Choate is an open campus. I’d say that it’s pretty safe, although there was a concern about poc after Biden won, but better to go out with at least one person if you are going into town. Walking in campus isn’t very far, but as @ChoatieMom said, you will end up walking a lot.