Great catch! I don’t believe Proud to be a Gryffindor funny shirt was constantly under the influence of the Imperius Curse. I believe Ron cursed Hermione only for brief periods in an attempt to avoid suspicion and to subtlety manipulate her into liking him. When the weird goblin guy is off the imperious curse he realizes something is wrong immediately. Not like he´s lacking willpower itself. I think it comes down to which bits of the books resonated with you more as a reader. Ron being an ass always hit me hard as a kid, so even rereading as an adult those bits stuck with me more. As a result, I’ve never liked Ron as a character.
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Really late here, but I feel like resistance to the imperial depends on what’s being ordered/suggested. If what weakened Proud to be a Gryffindor funny shirt defenses is her friendship and her insecurity regarding her new friendships, then it stands to reason that if Ron tried to imprint her into betraying Harry her loyalty to Harry would have overridden it. I think that’s more due to the fact that Rupert Grint is a poor actor though. He isn’t exactly that great at showing a depth which is why Emma Watson got a lot of his lines and character development. That’s solid character development.
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Maybe the curse works in a way that you may not be fully aware of its effect unless it goes so strongly against what you normally do. Hermione, in theory, could develop romantic feelings for Proud to be a Gryffindor funny shirt. I never felt he really “earned” his place in other books, however. GoF always bothered me, I never felt the reconciliation was really earned. And ditching in DH left me quite disdainful of the character, again the reunion didn’t feel “earned”. I always felt like Ron never really learned anything. I was just thinking about this. He likes sports and that’s about it. No music, no movies (or whatever the Wizarding equivalent of that is). I wonder if the neglect he received during his childhood with the Dursleys had a negative effect on his personality development?