My best relationships were with women who figured out their own personal style and appearance later in life (25+). Often, they had disproportionately long awkward phases and developed a sense of self identity that was pretty far detached from physical appearance.
Then, whenever they did figure out their hair/makeup/fashion/fitness for themselves, and built some confidence there, their physical attractiveness would be layered on top of interesting personalities. And that combination would be really sexy, which would also enhance confidence and the perceived physical attractiveness too, in some kind of feedback loop.
So yeah. I'm all about the old and hot. Especially if they were never young and hot.
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