As someone who grew up the love of creative expression the best thing you can do is to let him start deciding on the type of tattoos now already. Then let him look at it everyday till the day he gets it done. That way the spur of the moment tattoos which often lead to regret will be avoided. I designed most of my tattoos myself and bar the matching wedding one with the Ex i waited 6-24 months after designing before getting them done. Hence i don't regret any of them. You don't want to know how many designs i scrapped because they lost their appeal after a while.
