1. The First-Name, Last-Name Boy: Jack Kerouac
Jack Kerouac is the boy who you can’t help but refer to with his full name no matter how many times you’ve see him naked. This is because he always makes you feel tragically unhip in comparison with his uncanny ability to drop witticisms and snarky references that go way above your head. He pounds shots of whiskey like a champ and smokes so many cigarettes you wonder how he can still breathe like a normal person. Each time he texts you to “hang out” at one in the morning, you forget all semblance of self-respect despite knowing that he keeps a running harem of other girls who are similarly attracted to his tortured-intellectual mystique.
2. The Frat Star: Charles Bukowski
In 1978, Charles Bukowski published Women — what may be one of the most misogynistic pieces of literature in existence. The thinly disguised autobiography describes Bukowski’s numerous sexual encounters and how each lover sorely disappointed him. In other words, what Bukowski wants us to take away from this text is that he bags as many babes as he wants and that he is exceptional in bed. If Bukowski went to college today, he would make the perfect post-millennial frat boy whose game and war stories far outmatched those of his brothers. He would be that boy whose air of doucheyness is unbearable but who never has any trouble scoring with whomever he wants.
3. The Edgy Dude: Chuck Palahniuk
Chuck Palahniuk is the dude who stomps into class fifteen minutes late and then proceeds to spend the entire lecture browsing questionable 4chan forums and websites that are a part of the Deep Web. Occasionally, he’ll raise his hand and offer some sort of profound philosophical commentary — surprising both the teacher and the other students because he gives off the impression that he couldn’t give two shits about whatever his classmates are discussing. However, his love of anarchist symbols and noise metal mask some serious insecurities, as you’ll realize after he calls some girl 25 times in one night when she decides to stop seeing him.
4. The Self-Discoverer: J.D. Salinger
J.D. Salinger is the boy who has an almost crippling case of Poor Little Rich Kid Syndrome. He believes that going to class is a waste of his time; he’d rather be out in the real world, affecting tangible change. When he read Siddhartha at sixteen (because his social life then consisted of hanging out more with his high school librarian than his peers), it greatly changed his perspective on the world. He really likes kombucha and will move to a city like Portland or Austin after graduation in order to “make it big” as a writer. Eventually, he’ll end up moving back in with his parents when he realizes that he can’t sustain his love of craft beers on his own.
5. The Debra: Cormac McCarthy
Cormac McCarthy would not just be a Debbie Downer but he’d be a full-on Debra. He’s the boy you’d never want to take out with you because he’d spend the entire time constantly reminding you that you have class in the morning. He can get drunk off a single beer and three beers will put him to sleep like the precious, little baby he is. He probably hasn’t kissed a girl since high school. Though he can sometimes be a lot to handle, you keep him around because he proofreads your essays for class.
6. The Party Boy: Bret Easton Ellis
Bret Easton Ellis is the boy who is always down to party, any day of the week. He has an alcohol collection in his room that could rival any package store and talks so quickly and animatedly that you always wonder what he’s on. And — trust me — he’s always on something because sobriety is just too boring to handle. He studies finance in school, color-codes the alarming number of Brooks Brothers shirts in his closet, and dreams of marrying a beautiful blonde who knows how to distinguish amongst different serving utensils.
7. The Sophisticated Older Dude: Tom Robbins
Tom Robbins is the graduate student who hangs out in the coffee shop near campus — no, not the Starbucks. He spends whole afternoons there, sipping on cups of joe — skip the sugar and cream, please — and journaling in his moleskin. He wears horn-rimmed glasses, rocks a scraggly beard, and reads books that that The New Yorker told him to. You are attracted to his wide body of knowledge as well as all of the important life lessons he can teach you, and you don’t care how much your friends tease you for it.
8. The Cute Freshman (Ugh): Tao Lin
Tao Lin is the scrawny 18-year-old freshman boy you find yourself drawn to, against your better judgment. He occasionally has insightful things to say, but you find yourself cringing every time he makes a fart joke — which is all too often. You will hide your unfortunate crush on him from your friends for as long as possible.