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Through the wringer
Definition : To put someone Through the wringer : cause a lot of stress; give someone a hard time
A wringer is a machine that squeezes all the water out of something. For instance, all dryers have wringers. The wringers help get the water out of your laundry. If you tried putting a person through the wringer, it would not be a very pleasant experience. That person would be squeezed so hard, it would hurt. When you put someone through the wringer, it means you gave him a hard time. Maybe you made him feel uncomfortable, gave him lots of work to do, or asked him lots of personal questions
Examples
His wife put him through the wringer when she asked for a divorce
This new job is really putting me through the wringer. It’s really difficult
My dad put my suitor through the wringer the first time he met him, but he survived and now they get along great
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