It's generally believed that women understand men more than men understand women. Partially, it's because women are just more complicated than men are, as the diagram illustrates. However, there is at least one aspect of male psychology that most women simply do not understand, and that's the overwhelming desire to appear masculine.
Courtney doesn't understand why a man would balk at attending Mary Washington College; she has probably attended several schools that were named after men and she may never have thought twice about it. Despite the fact that MWC has a 65:35 female:male ratio, they're having trouble recruiting male students, and the mens basketball team is even having difficulty in finding opponents to play against. Courtney doesn't understand why this is the case, but I suspect that almost every man reading this is quirking his eyebrow knowingly.
Men are very dependent on their masculinity for attracting women, and women need to understand that every single decision a man makes is designed to maximize their chances of having sex with as many women as possible. From our clothes, to the cars we drive, to our majors in college, to the movies we see, everything a man does is directly or indirectly focused on being attractive to women. Everything. I'm not joking. Sure, we try and act as if this isn't true... but that's only because it makes us more attractive when we act like we don't care.
Women who are into some male-type things are a real turn-on for most guys. Men who are into female-type things are generally (a) denigrated by other men, and (b) dismissed as potential mates by most women. Sure, gay guys have tons of female friends -- but it's largely because they're safe and gay, which defeats the whole purpose! (Incidentally, some straight men have tried to take advantage of this by pretending to be gay, but I've never heard of it working out well.)
To sum it up: girl + baseball cap == cute; boy + flowers in hair == gay. Extrapolate to Mary Washington College.