Poor baby. If it makes you feel any better my teddy had 7 teeth extracted at 3.5 years old. They were nonvital teeth and they found this on the xray. But, the good news is that the fourth premolars are the chewing teeth so the thirds aren't as crucial. Does your vet do xrays during dentals? If not, I might go to someone who does so any other issues can be noted and addressed while Galen is young. I think flexi nylabones are fine, and wouldn't likely cause the loose teeth.
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