ANSWERS: 2
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I always thought it came from how a cow chews her cud. She does it over and over. So, chew on this meant think about it over and over (carefully). I could be completely wrong.
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In the past, most people, if they got meat, got the cheapest cuts. It was necessary to chew it much more than a prime steak, so gave you plenty of time to think. It is also related to the action of cows that chew their cuds or "ruminate".
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