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It depends on your situation, but some retainers can be wired in semi-permanently. It involves brackets being left on one set of molars and then the retainer is attached to that. Depends on the type of retainer...I would discuss it with your orthodontist.
 

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Would tylenol or ibuprofen help? I know not everyone on here uses those but I had braces as an adult and I found ibuprofen to help a lot with the soreness after orthodontic visits. It might help him to take some ibuprofen while he gets used to wearing the retainer. Really, after a couple days at most it shouldn't hurt anymore.
 
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