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In special relativity, simultaneity is relative to the observer's frame of reference. Say the boy did move fast enough such that the pole contracted, in the frame of reference of an outside observer, the two ends of the pole fit simultaneously inside the barn.
In the boy's frame of reference, however, the two ends of the pole would enter the barn not simultaneously as he is moving at the same speed as the pole; for him, the length of the pole would have not contracted.
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