Neither the Cap’n nor I were terribly popular as teenagers. The Cap’n was slight of build, asthmatic, severely myopic, and way too good at math to be socially sought-after. I lacked poise, hip sartorial taste, conventional beauty, and easy conversational manners. I preferred being funny to being admired, perhaps because I believed I would be laughed at in any event, and might as well earn the laughs through deliberate effort.
I’ve often wondered why it was that I didn’t try harder to be popular in junior high and high school, but I usually come back to the fact that the popular kids who were good-looking but of average intelligence and meager talent were not interesting to me as friends. I’ve always preferred to spend my time with people I admire, from whom I hope to learn something. It soon became clear to me that the more popular kids had nothing to offer me, so I left them alone.
But later in life, I came across another theory of why I didn’t apply myself more to the task of being popular. Back in 2003, the Cap’n came across an essay by Paul Graham, a highly successful computer geek. In this essay, Graham explores the phenomena of popularity, nerddom, and how high schools, suburbia, and contemporary society contribute to creating the (often hostile) teenage caste system that thrives in middle and high schools.
For former geeks, nerds, and other misfits; for schoolteachers; and for parents of budding schoolchildren, this essay is highly recommended reading. It’s VERY lengthy, but I’ll pull out a few choice extracts:
But in fact I didn’t, not enough. There was something else I wanted more: to be smart. Not simply to do well in school, though that counted for something, but to design beautiful rockets, or to write well, or to understand how to program computers. In general, to make great things.
…
Before that, kids’ lives are dominated by their parents, not by other kids. Kids do care what their peers think in elementary school, but this isn’t their whole life, as it later becomes.
Around the age of eleven, though, kids seem to start treating their family as a day job. They create a new world among themselves, and standing in this world is what matters, not standing in their family. Indeed, being in trouble in their family can win them points in the world they care about.
…
I think the important thing about the real world is not that it’s populated by adults, but that it’s very large, and the things you do have real effects. That’s what school, prison, and ladies-who-lunch all lack. The inhabitants of all those worlds are trapped in little bubbles where nothing they do can have more than a local effect. Naturally these societies degenerate into savagery. They have no function for their form to follow.
When the things you do have real effects, it’s no longer enough just to be pleasing. It starts to be important to get the right answers, and that’s where nerds show to advantage. Bill Gates will of course come to mind. Though notoriously lacking in social skills, he gets the right answers, at least as measured in revenue.
Reading Graham’s essay, I couldn’t help but wish that I’d had my 40-year-old brain when I was young. The things my peers did then that bothered me so much, and that my adult parents told me just to ignore, would have slid off my back much more easily. And yet I do derive some consolation from the fact that while I often felt snubbed, belittled, or calculatedly ignored by the kids called "socies," "snobs," and later, in college, "BPs" (Beautiful People), I never compromised who I was to try to become one of them.
Shimshonit 
Interesting analysis on the the idea that self-contained insular bubbles of pettiness cause the discrimination against the non-socially-gifted, causing some adults to experience the same caste-discrimination as middle-school children.
In any case, I remember learning in fourth grade that what other children thought of me was irrelevant. They were ignorant, and I knew that I was right. If they wanted to chastise me, that was their problem, and I wouldn’t be brought down by it. Finally, in ninth grade, it ceased to be an issue, as intelligence and ability finally overtook social skill as the key factor in popularity, though a healthy sense of humor still wasn’t a liability.