To dye, or not to dye?

So yeah. I bought me some of that black junk for your head. In simple terms, black hairdye.

But but but! I'm kinda scared to dye it.
I've been a burnette for so long that I'm not sure what the transition is going to be like.. or if my hair will fall out. Who knows. Though, here goes nuffin'.
I'm probably going to dye my boyfriend's hair black for him too.  I'm just afraid he'll mess it up if he does it, as a guy, lol. But I'm not doing it for that sappy couple matchy thing.  Both of us has actually had the color in mind for quite a while now.
Anyway.. I like your hair. Who does your hair?
I wanna go there.