Get a really good conditioner(no Walmart stuff), wash with DRY HAIR shampoo, put and leave conditioner on your hair for at least ten minutes. While the conditioner is still on, take a wide-tooth comb and start from the bottom. Take it an inch at a time. This will take a while, but might help. When you've got it all combed out, wait for it to dry and use a good-quality brush and brush GENTLY. When you go to bed, braid that section of hair that you have trouble with. Wet and condition it before you braid if you want.

I've had hair down to my ass for over 12 years and trust me...I know how you feel!