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Does he want the correction that the retainer will make but finds it too painful to use.....or....does he not want the retainer/correction at all? Is this a cosmetic thing or is there a medical need for it?

I'd take all of these things into consideration. If he wants it, then I'd call the orthdontist and see if some change can be made so that it's more comfortable for him. If he doesn't want the correction at all, and understands the results of not wearing it, then I wouldn't force it.
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