20 Literary Would-You-Rathers

1. Would You Rather have Captain Ahab give his mad soliloquy to you every night before you go to sleep or get swallowed by an actual White Whale?

2. Would You Rather have Jay Gatsby construct you with an idealistic perfection you could never realistically attain and pursue you with a fanatical zeal or have a Gatsby-themed wedding?

3. Would You Rather identify with Holden Caulfield or marry someone who still identifies with Holden Caulfield?

4. Would You Rather have Romeo compare you to the sun twenty-five times a day or stab thyself with a dagger?

5. Would You Rather be called “Humbert Humbert” or genuinely believe that Nabokov is a surrealist?

6. Would You Rather start every sentence with “All this happened, more or less…” or get SO IT GOES tattooed on your wrist?

7. Would You Rather wear an A on your chest for the rest of your life or defend naming a character Roger Chillingworth?

8. Would You Rather read Ulysses or listen to a double English/Philosophy major you’re out on a first date with explain the novel’s themes and plot?

9. Would You Rather be married to Richard Dalloway or actually have to host a party?

10. Would You Rather be a William Faulkner apologist or watch James Franco’s film adaptation of As I Lay Dying every day for the rest of your life?

11. Would You Rather look like the portrait of Dorian Gray in the end or have to get the last word in of every single conversation with the phrase “art for art’s sake, ya know”?

12. Would You Rather Sauron be your antagonist or Jack Merridew?

13. Would You Rather have actually read On the Road but nobody knows you read it or would you rather have never read On the Road but everyone truly believes it is your favorite novel?

14. Would You Rather have someone describe you as a monstrous vermin or be roommates with a young man who describes his struggles as Kafkaesque?

15. Would You Rather read all 379,000 articles that come up when you search “Is Jane Eyre a feminist novel” on the internet or say “Reader, I Married Him” to every new person you and your spouse meet?

16. Would You Rather read Alice In Wonderland every day for the rest of your life or sleep with a guy in your MFA program who has “A Raven Is Like A Writing Desk” above his writing desk?

17. Would You Rather listen to Gilbert Gottfried narrate the 38-hour audio version of Anna Karenina or date a man who must explain the Golden Era of Russian fiction every time he climaxes?

18. Would You Rather be a handmaid or a poet with a ton of talent who has to sell out and write a dystopian YA novel to make any morsel of cash?

19. Would You Rather have your sister novelist introduce your only novel with the lines “Whether it is right or advisable to create beings like Heathcliff, I do not know: I scarcely think it is” or admit that you had to google “What is a moor”?

20. Would You Rather actually admit you enjoyed Infinite Jest or carry the book around with you out in public everywhere you go for one thousand days?