Justin didn't get along with anyone. Not for any specific reasons, just thought he was better than everyone else.
Madeline's father purposely destroyed Orry's letters to Madeline and hers to him after a while because he wanted her to marry Justin. It's been years since I read the books, but I think Nicholas had suffered business reverses and was basically broke. While the Mains were as wealthy as Justin, Orry was young and it would be some years before he was in a position to marry. But Nicholas didn't tell Justin about the letters. If he had, Justin would have confronted Madeline.
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