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Are either of you using a save file that was taken from a memory card? If this is the case, are you sure the original Xbox profile owner is the same as the one you used when you "earned" the achievement? If it isn't the same, it won't register.
Though, truth be told, it has happened to me in Two Worlds and the Simpsons that I didn't receive an achievement when I should have (but did later on eventually).
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