Would You Rather...? The Big Book. Justin Heimberg
have sex with an auctioneer who speaks in auctioneer inflection during sex
OR
an aspiring rapper who freestyle rhymes during sex?
Things to consider: Try both.
Would you rather…
have sex with the fourth image when you Google “swarthy”
OR
the third image when you Google “albino”?
Things to consider: Make your choice before Googling, then check and see what you are dealing with.
Would you rather…
have sex with Lady Gaga and then have to wear her outfits for a month
OR
have sex with Dame Judi Dench?
Would you rather…
have sex with the 4 out of 5 dentists that recommend Trident sugarless gum
OR
the 5th dissenting dentist?
Things to consider: Do you like rebels? Rebels with tooth decay?
WHERE’D YOU RATHER…?
Would you rather have sex…
on the monkey bars OR on a seesaw?
on you parents’ bed when they are out OR in the room adjacent to your parents’ room (separated only by a thin wall) while they are home?
in a plane restroom (mile high club) OR in a train restroom (4 foot high club)?
in the pit with all those balls in a Chuck E. Cheese play area OR in a convertible while it is going through a carwash?
on a bed of nails in private OR on a luxuriously soft bed at Mattress Discounters during a Columbus Day sale?
Would you rather…
have sex with Bono OR Elvis in his prime?
Jason Mraz OR Jack Johnson?
Dave Matthews OR Rob Thomas?
Things to consider: What if each serenaded you first?
Would you rather…
have sex with Beyoncé OR Christina Aguilera?
Madonna now OR Britney Spears when she turns 50?
Lindsay Lohan sober OR Lindsay Lohan messed up?
Would you rather…
have sex with a die-hard liberal who’s conservative in bed
OR
a die-hard conservative who’s liberal in bed? Who’d you rather marry?
Would you rather…
bang the office hottie on your boss’s desk
OR
your high school crush in the principal’s office?
Would you rather…
have sex with Steve Carell OR Stephen Colbert?
Derek Jeter OR Kobe Bryant?
Joel McHale OR Robert Downey, Jr.?
Tom Colicchio OR Simon Cowell?
The Manning brothers OR the Jonas Brothers?
Would you rather…
have sex with Kristin Kreuk OR Brooke Burke?
Marisa Miller OR Adriana Lima?
Sharon Stone in her prime OR Kathy Ireland in her prime?
Minka Kelly OR Minka the porn star (world’s largest-breasted Asian)?
Pelbin Frolkdarp OR Lelsgahn Nasklope? (Go with your instinct.)
BAD BREAKS: WEIRD, WILD, AND WARPED
For reasons beyond your understanding, you are about to be stricken with a terrible curse: a crazy compulsion, a deranged deformity, a perplexing personality disorder, or some other brutal-for-you, entertaining-for-everyone-else affliction. Sometimes, a curse can turn out to be a blessing in disguise. Other times, not so much…
Would you rather…
impulsively shout “Follow that car, and step on it!” every time you get into a vehicle
OR
invariably start all your sentences with “Negro, please!”?
Would you rather…
have orange Jell-O phlegm
OR
have glittered sweat?
Things to consider: possible stripper career
Would you rather…
for the rest of your life, have a two inch splinter of wood inescapably stuck in your head
OR
have the song “Afternoon Delight” inescapably stuck in your head?
Would you rather…
compulsively police-frisk everyone you meet until “they’re clear”
OR
passionately kiss anyone and everyone whenever you say goodbye?
Would you rather…
only be able to express your feelings by bursting into Broadway-style song and dance
OR
only by using PowerPoint presentations complete with charts and graphs?
Would you rather…
realize you have gum caught in your pubic hair
OR
realize you have pubic hair caught in your gum (after five minutes of chewing)?
Things to consider: This question excerpted from the Socratic Dialogues.
Would you rather…
hear all music in 8-bit Nintendo DS sound quality
OR
mistakenly push on every “pull” door for two minutes before figuring it out?
Would you rather…
automatically bitch slap anyone you’re speaking with who makes a grammatical error