That is not a predicament I have had to ponder personally, as I am of a short enough height that heels are a non-issue when compared to the average height of boys at this school. The social standard that expects a man to be taller than a woman, even when she wears heels, may trace back to the role of men as protectors. Thus, when women are shorter, they may appear to be weaker than the men they are with and in need of protecting. Many female students here have made it clear they do not need protecting. In such a case, any issues men have must be lingering insecurities due to social expectations.
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nunneries) wrote,