I trim my husband's toenails (and fingernails) right after his bathing (shower) ritual. He's grumpy as all get out getting him ready to shave and shower and during but afterwards he feels so good. (It's good to be clean!) After I help him dry off, I powder him which makes him feel so good then help him into clean underwear and t-shirt, then often times his pjs. I will then inspect his feet. About once a week or every two weeks I trim the toenails after inspecting. I trim his nails and use an emery board after to smooth. His fingernails are not very good but have improved with supplements, frequent grooming and a nail strengthener I apply. My husband is blind due to an aggressive form of glaucoma, has diabetes and dementia. He requires 24/7 care and I'm his sole caregiver. If you can make his footcare part of his shaving and bathing activities, you might have better luck with him. I realized my husband is more amenable after his shower, powder, dressing so I took advantage of that to trim his toenails. I use a happy cheerful voice and he gets with the program. If this doesn't work for you, I would suggest taking him to podiatrist for toenail and footcare on a regular routine basis.