I have blue eyes, and have naturally very dark, almost black hair and I don't look pale. So good luck!!
When you deposit colour into the hair it's much less damaging than taking colour out.
My hair has been every colour of the rainbow, and yes it did get a little damaged back in the day when I was experimenting with colour alot. But I was bleaching, and highlighting, and lowlighting and...etc.
I've dyed and lighlighted my hair all in the same day so I wouldn't have waited, but that might not be the best advice hahaha
I'm actually hoping to go to hairschool when I can save enough for the tuition...it's pretty expensive $7000 for the ten month course at the best school here.
I like dark hair, it's easier to take care of and always looks healthier than going light.
If it ends up a bit dry, do a treatment once a week. My fave is the regular V05 hot oil.
I hope it looks great, I'm sure it will.