Corrected entry: There's no reason why a wheelchair-bound boy should wear a sweat suit during school sport. He isn't taking part, so he could just have kept on his usual clothes. Changing his clothes just to "fit in" wouldn't make much sense as it takes some time, if not assistance, for a paraplegic to get changed; apart from that, Roland isn't the type of guy who wishes to fit in.
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Correction: No, but bullying him into changing his clothes so that she could feel like she was helping him to fit in, is exactly the kind of thing Hilary Faye would do.