In many cases this is a woman walking on eggshells trying to figure out what a man would most prefer from her. Some men would be horrified to be out with a woman who is standing taller than he, with or without heels. Other men couldn’t care less. Some men would feel disrespected if a woman chose to wear heels that then made her appear taller than him. Others couldn’t care less. Some men find more flat shoes on women to be ugly and unattractive. Other men couldn’t care less. Some men would feel disrespected that a woman didn’t dress up in heels for him, when going out. Other men couldn’t care less. Some men are turned on by a woman wearing sexy heels and prioritize that over how tall she may appear, relative to him. Other men may find heels super sexy but never want to be seen as shorter than her, in public, so heels are out. And on the possibilities go on. How is she to know which man he is?
Some men have no issue discussing the topic openly. It bothers them not at all. Others are super sensitive and immediately interpret the fact that she is even hinting at the topic, as a personal judgement of him and his height. So rather than be direct many woman will hint to hopefully get some greater understanding of what the man she is seeing prioritizes and prefers.
Many women hint/ask in this way, as an attempt to inoffensively find out what would most please YOU, the man they will be seeing.
What would you like her to wear? Sexy high heels no matter what, low heels so not too much taller but still attractive, flats so not ever taller than you, or you couldn’t care less and she should just dress however she feels attractive/sexy and ready for a good time with you.
If a woman brings this up, it is not necessarily a woman negging a man and his height. It often is a woman seeking to dress to please the man and gain his further approval.
Be careful of assumptions. Before you know it, assumptions can limit one’s perspective. And that limited perspective can then significantly limit a person from achieving their desired results.