I think my biggest "huh" moment with respect to gender roles is when it was pointed out to me that your typical "geek" is just as hypermasculine as your typical "jock" when you look at it from the right angle.
As male geeks, a great deal of our identity is built on the notion that male geeks are, in some sense, gender-nonconformant, insofar as we're unwilling or unable to live up to certain physical ideals about what a man "should" be. Indeed, many of us take pride in how putatively unmanly we are.
Viewed from an historical perspective, however, the virtues of the ideal geek are essentially those of the ideal aristocrat: a cultured polymath with expertise in a vast array of subjects; rarefied or eccentric taste in food, clothing, music, etc.; identity politics that revolve around one's hobbies or pastimes; open disdain for physical labour and those who perform it; a sense of natural entitlement to positions of authority ("you should be flipping my burgers!"); and so forth.
And the thing about that aristocratic ideal? It'sintenselymasculine. It may seem more welcoming to women on the surface, but - as recent events will readily illustrate - this is a facade: we pretend to be egalitarian because it suits our refined self-image, but that affectation falls away in a heartbeat when challenged.
Basically, the whole "geeks versus jocks" thing that gets drilled into us by media and the educational system isn't about degrees of masculinity at all. It's just two different flavours of the same toxic bullshit: the ideal geek is the alpha-male-as-philosopher-king, as opposed to the ideal jock's alpha-male-as-warrior-king. It's still a big dick-measuring contest - we're just using different rulers.