Why does a negative times a negative equal a positive? Does this ever happen in the real world?
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Study some field theory and you will find out a why; mathematics is tested only by logic (in the most general sense). – Yes Oct 17 '15 at 04:42
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One way to picture this is to imagine a number line. Then rotate it $180^{\circ}$. Each number will now be superimposed over its negative: $-1$ will be where $+1$ was; $+2$ will be where $-2$ was. Rotation of the number line by $180^{\circ}$ is the equivalent of multiplying by $-1$.
Now do the rotation twice. The number line is unchanged. So, multiplying by $-1$ twice is the same as multiplying by $+1$.
This approach has applications with Complex numbers. In these scenarios, the number line is rotated $90^{\circ}$ counter clockwise to multiply by $i$.
But that's another story.

MathAdam
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