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Are his whiskers soft or stiff? If they’re stiff, get him some beard oil/conditioner and it’ll soften it up. I’ve been wearing a beard for two years, it’s not a bushy beard, I prefer to keep it trimmed close and tidy, but some oil and a good conditioner (and face wash, of course) keeps it soft.
I feel your pain. I usually put panthenol on the affected areas right after. it helps to at least not have any peeling dry skin on the days after.
Grave before shave has a ton of products for beards. I use the beard butter and balms to keep mine soft. Also get some beard wash to help out. They have a variety of smells. My wife bought me them when we were first dating for the same reason
There are oils / conditioners specifically made for facial hair. Try some of them.