As
@si_c said above, but just to add, might it be that the spokes on the opposite side of the wheel are still in tension, so when trying to screw in the nipple in situ, you can't get past those first few worn threads? If so, and you're confident you can retrue the wheel, release the tension in the opposite side of the wheel first, then try adding the nipple.
Also, you could substitute a nipple from an adjacent spoke to identify whether the original one is at fault. If the replacement works fine, then replacing the worn one would make sense.