No, it does not always hurt. It depends on the person, and also how far gone you are.
I had a miscarraige over a month ago, and i did not have any pain, and just experienced a light period for about 5 days.
My friend has a miscarriage last year, and had unbareable pain, and bled really heavy for an hour or so.
Like i said it depends on the person and how far gone you are.
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