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This answer originally appeared on Quora. We have left it mostly unedited.
I suppose that I’m in the target demographic. I’m (1) a girl, (2)
book-lover, and (3) a humanities major. I was, however, a history major, so let’s see what
that means. I’m afraid that my tastes aren’t highbrow enough for you, but I’ll do my very
best to help you in your noble quest. Before we proceed, I need to point out a
contradiction. You say that you want to sound smart in a hot and a douchey intellectual
way. I’m afraid these two things are mutually exclusive. Douchey intellectuals aren’t hot
or necessarily smart. In fact, it may be a turn-off to have someone throw around book
titles to sound like their pants are just full of smarties. Just sayin’.If
you’re determined to stay on the douchey side of the spectrum, it takes more than just
reading fancy books. It’s about the attitude. A few tips:Tone
– Try to keep your tone as condescending as possible. For example,  you should
disparage all obvious metaphors such as, “The metaphor of water in The Great
Gatsby
is just too utterly obvious. It’s about the boat.”Language
– If the book was written in a non-English language, use its original title and
pronounce it correctly. For example, use Les Liaisons dangereuses instead of
Dangerous Liaisons. Extra douche points if you read these books and quote
passages in their original language.Age – Put down newer
books in favor of older, incredibly difficult to read books. This isn’t a hard and fast
rule though, thanks to David Foster Wallace. But always, always turn up your nose at
popular fiction. The Hunger Games? Shockingly bad!Discussion
points
– Stories, plots, character development? How pedestrian. Talk about the
beauty of Henry James’ and Borges’ writing. You don’t even need to read them, just say
that their prose reminds us of our fragile humanity (whatever that means).If
you want to be a hot literary nerd, all you need to do is to tell the girl what you
actually thought of the book. With this list, you’ll be able to go either way:
hot nerd or douchey intellectual. It’s all about the tone.Ulysses (James Joyce): They teach entire college courses
devoted to this book. You can’t beat an eye-patched author for panache!Infinite Jest (David Foster Wallace): Fractals! How could a girl not
swoon about a book that combines philosophy, mathematics and humor?Anything by
Jorge Luis Borges: I’m not even sure Borges understood his books either.
So, you can say whatever you want about them, it’ll sound plausible.Anything
by Jane Austen: Not only will she think you’re smart, but she’ll think
you’re a hot sensitive hunk who understands women. Just don’t compare the girl with Fanny
Price.Major philosophical works of Jean-Jacques Rousseau,
John Locke, Thomas Hobbes, Jean-Paul
Sartre
, Simone de Beauvoir and Rene Descartes:
I’d start with No Exit by Jean-Paul Sartre, at least that one is
fun to read (and short). Major tragedies by William
Shakespeare
: No Tempest for you, they teach that in middle school, for
goodness’ sake! It’s about the epic tragedies: King Lear, Macbeth, Hamlet, et cetera.
These tragedies will allow you to be emotive, intellectual and hot all at once. (Romeo
and Juliet
is cheating though.)Of course, I’m just scratching the surface
here, but being a douchey intellectual is work. Postscript: beware of going too obscure. A
girl won’t be impressed by something that she has never heard of.

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