Often times when patients complain of sensitivity when flossing they actually have proximal erosion. Buccal abfractions can extend into the mesial and distal surfaces of teeth, leaving sensitive areas of the teeth that are not decayed. Also, many patients have proximal areas that are denuded of their natural protective coating (either enamel or cementum)at the cervical (neck) of the tooth, probably exacerbated by frequent scalings(even good things have a downside).
Unfortunately there other reasons that it can hurt to floss. Teeth with large intraproximal caries lesions ( large cavities) can experience pain when flossing. Similarly, people with loose filling can also have pain when they floss, since the floss can cause micro-movement of the their filling.
Sometimes inflamed interproximal gingiva can hurt after flossing. This happens because the inflamed gingiva is swollen and edematous and gets sore when it is touched by anything. Fortunately, if this is the cause of pain it will self correct if flossing is continued over the next week since the gingiva will usually respond by becoming healthier.If the gums continue to hurt, even if flossing continues, it is possible that the person flossing is not using the proper technique and is "cutting" their gums.
Obviously, if you are having pain when flossing, the safest bet is to arrange a visit with your dentist and let him or her know where you are having the pain. They should be able to pinpoint why and what to do about it.
Direct copy from Dr. Spindel on September 16, 2020: http://www.lspindeldds.com/askdr/
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