No, I've never noticed any nefarious dating market conspiracy against high achieving women either. True, I am probably vastly dumber than de Beauvoir, Arendt, or even Kagan, and most of my relevant anecdotal evidence concerns women who are high achieving in a more ordinary sense of the word. And yes, I found middle and high school painful in that regard. But the real issue there was that "high-achieving" meant "different", and different meant dating was difficult. But there were all sorts of other ways of being different in high school that made life difficult, and high achieving probably wasn't necessarily the worst sort of different.
I also find it weird that the Roissy types so often claim that there's some vast supply of working class, non-ambitious women out there who are vastly more attractive than their high achieving sisters. As far as I'm able to tell, the three big constraints on female attractiveness are genetics (being blessed with nice bone structure and so forth), money , and time. The first seems randomly distributed across all levels of female achievement. While there are high achieving status income disequilibrium babies who lack the second (writers, art historians, non-profit leaders and so on), even they usually wind up fairly well off eventually. It's much easier to eat healthfully, buy flattering clothes, and so forth if one has money than if one doesn't.* I suppose high achieving women do lag as a group on the third: needing to devote time to school and work necessarily means less time spent on one's looks. But... one can balance out vulnerability on #3 via consumption along dimension #2, which suggests that not all is bleak for the ambitious among us.
Note also that any discussion of Kagan groupies or lack thereof should include a nod to this Craigslist ad.
*This may be another example of libertarian tendencies coming to the fore, but in my admittedly anecdotal experience, expensive goods and services usually are better in some way than their lower priced equivalents. That is, expensive dresses do not exist merely because the rich are evil and want to flaunt their wealth conspicuously over everyone else.