Aww poor baby, I've never done that cause I've never actually clipped a dogs nails before, the vet usually does it for me; however we bought a pedipaw trimmer to hopefully prevent things like that. I'm not sure how it works yet, haven't used it but when I do I'll use it on my bigger dog first since she isn't as brittle as our yorkies are. I'm sure he'll forgive you soon, dogs are very forgiving!!