Regardless of Hillary's political fate, she'll never be able to win the challenge of being perceived as both a good candidate and a likable person.
Two years ago when Clinton was gearing up for the presidential race, Time magazine hit the nail on the head with a cover that featured Hillary's face and the words: "Love her, Hate her (check one)."

My cousin and I wrote an op-ed on the topic last February. Many of our critics thought we were endorsing Hillary and accusing her opponents of being prejudiced against women. I admit the editorial could have been written in a less biased way, and I hope I won't make the same mistake in this blog entry.
My goal was to point out that the widespread polarized reactions to Hillary can be explained by several lines of psychological research. Susan Fiske at Princeton has demonstrated that people's stereotypes about women tend to fall along two disparate dimensions: warmth and competence. Consequently, women must walk a precarious tightrope -- the more competent they seem, the less people like them.
Alice Eagly of Northwestern University has devoted decades to understanding people's reactions to women's leaders. She's found that people tend to evaluate female leaders unfavorably because the traits that people typically associate with women (e.g. warm, caring, nurturance) are antithetical to the traits people typically associate with good leaders (e.g. strong and assertive). Eagly has also found that women who lead in masculine ways tend to be disliked.
Granted the research mentioned above was done primarily with college students, a sample hardly representative of the general population. However, to this I must argue: college students tend to be more liberal in their political and gender attitudes than the rest of the country. If college students can't allow a woman to be both nice and competent, where does that leave the voter sample at large? Its also worth noting that in most studies, women are just as likely as men to dislike a woman leader.
Regardless of whether Hillary wins, it is my hope she will help us better understand the role gender plays in politics. Hopefully, in time we will realize that gender discrimination doesn't have to be motivated by hatred or insecurity; instead, our deeply cherished beliefs about the roles played by men and women in society can sometimes lead to unfortunate prejudices.
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Further Reading:
Eagly, A. H., & Carli, L. L. (2007). Through the labyrinth: The truth about how women become leaders. Boston: Harvard Business School Press.
Eagly, A. H., & Karau, S. J. (2002). Role congruity theory of prejudice toward female leaders. Psychological Review, 109, 573-598.
Fiske et al. (2002). A model of (often mixed) stereotype content: Competence and warmth respectively follow from perceived status and competition. Journal of Personality and Social Psychology, 82, 878-902.