I have a medium darkish brown hair and I want to get high lights. I'll also tell you that I'm pale skinned and I have green-gray eyes. It's just that I don't want to get a color that looks bad. Help...

Get gold toned high lites. Looks really nice in the summer.
You could try sun in.

I like reddish highlights in the fall.

Gold highlights are going to be too harsh against your pale skin... ask your stylist for neutral colored highlights to stay away from the brassy look.