Stories Link Copied 10.30.24

17 Would You Rather Questions That Go Deep

Get out of a small-talk rut with these thought-provoking dilemmas. ByAnna Borges

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If a teenage sleepover was the last time you dabbled in a game of Would You Rather, you’re missing out. While the biggest debate back then probably centered around something silly (like if you’d rather fight one horse-sized duck or a hundred duck-sized horses, or live without pizza or french fries forever), Would You Rather questions for adults can actually lead to surprisingly deep and thought-provoking conversations. 

Despite their juvenile reputation, certain Would You Rather questions can be a fun and effective way to get to know someone, from strengthening existing relationships to checking the vibe with someone new. “The hypothetical and playful structure can lower defenses and encourage vulnerability, prompting open and honest sharing without the fear of judgment,” says Harville Hendrix, PhD, a couples counselor and coauthor How to Talk with Anyone About Anything.

His coauthor, Helen LaKelly Hunt, PhD, adds that the limited parameters of Would You Rather questions—this or that, no cheating!—can force us to reflect on specifics and new possibilities, rather than defaulting to our go-to answers or getting overwhelmed by choice. Plus, “they create space for the exploration of our personal values and thought processes,” she adds. 

So whether you want to puzzle through them on your own or quiz someone else to understand them better, here are some Would You Rather questions for adults that cover everything from dreams and fears to values and priorities: 

1. Would you rather have a perfect memory or be able to forget anything you wanted at will?

“Everyone’s got a different relationship with their past, and it’s cool to see how they’d handle it if they had a choice.” —Noah K., 27

2. Would you rather always feel understood or always feel appreciated?

“We all want to be seen, heard, and valued in our relationships. This question opens the door to a deeper discussion about the need for both understanding and appreciation.” —LaKelly Hunt

3. Would you rather wake up in Freaky Friday or Groundhog Day?

Not literally—whether you’d rather be Lindsay Lohan or Jamie Lee Curtis is another question. But when it comes down to it, you get a sense of how someone deals with change (or lack thereof) when posing the question: Would you rather move forward in someone else’s body or be stuck in a single (ever-repeating) day as yourself?

4. Would you rather be recognized for your intelligence or your kindness?

“This question can spark a discussion about one’s deepest desire for validation, and how they want to be perceived and seen by others.” —Hendrix

5. Would you rather know when or how you’re going to die?

“It’s death. Deep’s kind of in the description. But I like this one because it also gets people talking about destiny. As in whether they’d want to know how they’re going to die so they could attempt to thwart it.” —Jessie F., 42

6. Would you rather time travel to the past or future?

“It tells you a lot about people. More sentimental people might want to experience a specific moment. Some people want to alter history. Some want to see themselves in the future. You get a decent idea of what peoples’ priorities and interests are.” —Maggie L., 35

7. Would you rather give up social media or movies and TV forever?

“How someone interacts with media in general tells you a lot about them, especially these days. I care less about the actual answer and more how they puzzle through it—would they miss news, connecting with others, escaping into stories, etc.?” —Madison C., 23

8. Would you rather always tell the truth or always be able to tell when someone is lying? 

“Honesty and trust are biggies in relationships, and this question draws out different perspectives on that.” —Ryan S., 32

9. Would you rather never be able to celebrate your birthday again or have to throw a big party every year?

“IDK, man. People are weird about their birthdays. I feel like it always opens a can of worms on how they feel about themselves, attention, and their current social life.” —Lauren V., 31

10. Would you rather have more time or more energy?

“It’s simple, but people’s responses show how they deal with stress and priorities.” —Connor E., 24

11. Would you rather be able to control the weather or the traffic?

“It doesn’t sound that deep but I enjoy hearing about people’s mundane annoyances. You city folk can swap in public transit.” —Julie D., 28

12. Would you rather be loved for everything you’re not or liked for everything you are?

OK, so an old therapist of mine once posed this one when I asked for some session starters on a slow day. But it really does dig into whether someone prioritizes acceptance or authenticity. 

13. Would you rather have unlimited knowledge or unlimited creativity?

“The trick is no one quite knows what either would look like in practice, so it’s fun hearing people imagine it either way.” —Alexis Y., 26

14. Would you rather give up all the memories or money you made this year?

“I always ask this at my New Year's Eve parties. No matter what someone chooses, it’s a quick way to zero in on whether they’ve had a good year or a bad year and why.” —Emily J., 30

15. Would you rather know what the happiest day of your life or the worst day of your life will be? 

"Most of us spend a lot of time anticipating (and ruminating over) the good and the bad instead of letting life happen. But do you actually want to know how your life will go? This can open up a deep, sort of existential conversation, or at least make you wonder whether you’d prefer knowing that the worst or the best is yet to come—or already behind you!” —Sam B., 29 

16. Would you rather have the ability to hit pause or rewind on your life?

“This question is pretty much asking if you want to relive the past or lengthen the current moment on demand. I love it because you'll learn more about whether people skew more sentimental about the past or appreciative of their lives right now.” —Ashley O., 34

17. Would you rather never be able to show emotions or never be able to hide them?

“I love this for seeing how comfortable people are with vulnerability versus privacy.” —Kayla D., 25

18. Would you rather fight 100 duck-sized elephants or one elephant-sized duck?

Yeah, I had to end with the classic big duck vs. army of tiny elephants face-off. It might not be that deep, but when I asked one friend, he declared he’d take on the elephants “as long as he could stand on a study platform above them with a scythe,” at which point I learned he had excellent problem-solving skills. Another friend shuddered and said, “A million elephants if I can avoid even one duck,” which led to us swapping traumatic duck pond-related incidents from our childhoods. 
My point is, a Would You Rather question doesn’t have to be deep to get deep. Half the fun is listening to someone work through the question—and seeing where the conversation leads from there.