I already knew it was going to be tough on us. He's 11yo and the whole grooming thing just isn't a top priority for him (actually, NOTHING in life is a top priority for him these days). I told him that he could grow his hair, since that's what he wanted to do, as long as he kept it looking nice.
He's the type of child that likes to roll around on the floor and things (think about the things that your toddler probably does and that's what he does)....so his hair is always a mess. Then when I mention something about his hair to him he still doesn't take the initiative to go and brush it without being told to. Well, I can't tell you how many times each day I have had to tell him to brush his hair because it just looks awful!
So, I told him just a few minutes that he has ONE more time for me to have to tell him something. I'm sick of it looking bad and he's sick of me talking about it.... I predict that someone will be getting a haircut on Tuesday after school.
Re: Allowing DS#1 to let his hair grow is a nightmare!
It doesn't show up as messy in pictures because it's so dark....but when you look at it in person and up close....DISASTER! He just always looks like he needs to brush his hair....
It's hard for me too, because I like for my boys to be clean cut (and shaven...lol). A lot of times I look a hot mess, but it's because I spend most of my time worrying about their looks.