…Or whoever, just have fun and don’t take these questions too seriously!

Before smart phones and social media seeped into our lives like the plague, I remember growing up and playing games like “Would You Rather”.   Not unlike the infamous “Truth or Dare,” “Would You Rather” is a game that’s been around for decades now and doesn’t require more than a room full of instigating preteens.  As you can probably surmise, the gameplay consists of friends providing one another with hypothetical ultimatums, in which the game gets more fun as the options get, well… shittier.   And, don’t get me wrong, this game is always fun, but sometimes it’s hard coming up with realistic questions.  I remember, as a preteen, a lot of questions involved shaving your head because we were low on creativity.

So, Here’s My New, Wine-Induced List Of *Hopefully* Not-Lame “Would You Rather” Questions:

*Warning: I’m on glass #2 of wine for the night and I’ve been really into true crime lately, so this may not be the most family-friendly list… hence the 21+ age recommendation!)

1. Would you rather win the Lottery or not have to pay taxes?


2. Would you rather go to work in dirty clothes or, assuming it’s the only thing clean, a superhero costume?

3. Would you rather be talented and poor or wealthy because you have good connections?


4. Would you rather find a spider in your hair or a snake in your house?

5. Would you rather get a degree in Latin or break both of your arms at the same time?


6. Would you rather write a hit novel or direct a successful movie?


7. Would you rather be allergic to nuts or lactose intolerant?


8. Would you rather date someone who says “pasketti” or date someone who says “supposably”?


9. Would you rather run out of gas in the middle of nowhere or drive 100 miles in the wrong direction?


10. Would you rather be a hitchhiker or pick one up?

11. Would you rather live in your parents’ house or rent an apartment in the same building as your boss?


12. Would you rather knowingly date a criminal or not know your significant other is leading a double life?


13. Would you rather only be able to watch Ryan Reynolds movies or only be able to watch Nicolas Cage movies?


14. Would you rather watch a Nicolas Cage movie or listen to a Nickelback album?


15. Would you rather wear combat boots or socks with sandals for the rest of your life?

16. Would you rather buy second-hand underwear or go commando every day?


17. Would you rather take a car ride from Lindsay Lohan or Stevie Wonder?


18. Would you rather not be able to smell or not be able to cook?


19. Would you rather only eat unfrosted Pop Tarts or become addicted to meth?


20. Would you rather work next to someone with incredible BO or get laid off?


21. Would you rather have a child who’s a know-it-all or have a child who talks to ghosts?


22. Would you rather watch the movie Her every day for a year or work for Gwyneth Paltrow at Goop for 2 years?


23. Would you rather date someone obsessed with being “politically correct” or date someone who doesn’t speak English?


24. Would you rather work for a pyramid scheme or accidentally join a cult?


25. Would you rather stick to a vegan diet or have to hunt and gather your own food?


26. Would you rather lose everything you own in a fire or get locked away for a crime you didn’t commit?


27. Would you rather find out your pet rat escaped or your pet tarantula escaped?


28. (Men) Would you rather have a comb-over or shave your head?  (Ladies) Would you rather date a man with a comb-over or a man with a shaved head?


29. Would you rather eat spinach or bacon if the calories were the same?


30. Would you rather slowly turn into your mother or start speaking in a fake British accent like Madonna?  (Substitute for a fake American accent if you’re actually British.)



You may also like: Would You Rather Questions (Tough Life Choices for the 21st Century Adult)


Thanks so much for playing!  Feel free to share this post with a friend!

Would You Rather Questions