You are about 650 miles from one another.
When you look at the sky your visual range is in the shape of a cone, that meens that you couldn't see what your friend saw 650 miles to the north-west and he could'nt see the same range to the south-east .
That is not a significant distance, so you should have saw almost everything your frienf saw.. Maybe you had different visual condition as light and cloudiness.
The rule is - the distant you are from one another, this is the the range in the sky you would'n be able to see.
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