Robin Sutherns | Jun 29, 2020 | 0
69 Deep Would You Rather Questions – Spark interesting conversations.
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Deep would you rather questions are important for guys because you’ll need to understand not only yourself but your loved ones and new acquaintances at the deepest level possible.
It’s hard to think of enough would you rather questions on your own to keep the game going, so we’ve compiled some great ones for you in these accessible lists.
We’ll offer you some guidance on how deep questions to ask can be unpacked, unfolded, and understood to imply all kinds of important things about the person and people before you.
Make sure that you are not only armed with questions to ask but that you are able to listen deeply with undivided presence to the answers. Nobody wants to share more with someone who’s texting and half-conscious. Look them in the eyes, and allow yourself to be moved by their responses. Be the attentive listener that the world needs.
This game can be like interpersonal meditation. Notice everything about the person you are sharing with and who is sharing with you. Notice their smile, the way they breathe, their posture.
Here are the 7 best deep would you rather questions:
1. Would you rather have real political power but be relatively poor or be ridiculously rich and have no political power?
Do they view political power and wealth as separate entities when really the two can be wielded as one? You’ll perceive any limitations they have around how they view wealth’s potential.
2. Would you rather have the power to gently nudge anyone’s decisions or have complete puppet master control of five people?
The latter sounds like a much more insecure person would leap on that chance at power play. Big red flag.
3. Would you rather live in a utopia as a normal person or in a dystopia but you are the supreme ruler?
You’ll presence the quality of their hunger for authority or lack thereof.
4. Would you rather snitch on your best friend for a crime they committed or go to jail for the crime they committed?
How loyal are their friendships, and how afraid are they of jail?
5. Would you rather lose the ability to read or lose the ability to speak?
You’ll understand whether the person values their input or their output abilities more right now. The juiciness of this inquiry is why they chose what they chose.
6. Would you rather have a criminal justice system that actually works and is fair or an administrative branch that is free of corruption?
You might find out where they perceive systemic issues are most to blame.
7. Would you rather be born again in a totally different life or born again with all the knowledge you have now?
You’ll find out how satisfied they are with their current state of incarnation.
Some questions to ask a girl are going to be your cornerstone for better understanding her, yourself, and all others.
Observe your own internal reactions to her responses. Do you notice yourself eager? Tense? Anxious? Afraid of being misunderstood? Feeling superior? Are any of those reactions real?
8. Would you rather find a dead body or be a witness to a deadly assault?
This one seems to weigh the heat of the moment with the aftermath.
9. Would you rather always be overdressed or always be under dressed?
You might already sense her answer based on what you’ve seen her in up until this point. But you’d be surprised what her answer is and whether it differs from your assumptions.
10. Would you rather have a pause button in your life or a rewind button
The rewind button speaks of regrets. The pause button speaks of living a life too fast-paced to process.
11. Would you rather lose all of the money you’ve earned this year or lose all of the memories you’ve gained this year?
Does she value sentiment or practical security more? Did she have a year enjoyable enough as to cherish the memories?
12. Would you rather work a high-paying job that you hate or your dream job with only enough money for basic necessities?
Are practicalities and material luxuries tantamount or personal integrity and truth? Is she smart enough to reply that all timelines are temporary and we all must make sacrifices?
13. Would you rather find $100 floating in a public toilet or $5 in your pocket?
How germophobic is she?
It’s integral to have a nice solid list of questions to ask a guy so that you’re growing your circle of good guy friends always.
14. Would you rather want to be 5 minutes early or always be 5 minutes late?
Five minutes early is really a pretty responsible thing to shoot for in life, as it indicates a person is getting their mental mind ready for what’s to come. Always being five minutes late intentionally is kind of disrespectful.
15. Would you rather go hunting or fishing?
This comparison can go a million ways. We’ll keep it short: Land or water?
16. Would you rather do a risky business or get a good salary from a permanent job?
We assume this means that risky business means high stakes payout. It’s a decent question.
17. Would you rather save someone’s life and get killed or save yourself and let the other person get killed?
Wouldn’t that depend on who that other person is?
18. Would you rather work easily for someone else or work hard for yourself?
This is a question of whether they can handle being a little scared and unstable every day as an entrepreneur in charge of all the big decisions.
19. Would you rather live in the wild or stay on the streets of your city as homeless?
You’ll find out how scared they are of the woods and its creatures or that they see themselves in harmony with nature and capable of surviving.
20. Would you rather want to be famous when alive or when you are dead?
Fame has all kinds of drawbacks. It’s a question of whether privacy is of greater value to them than influential power.
21. Would you rather like to stay hungry for 4 days or eat every 4 minutes?
Some people hate being too full and so eating every 4 minutes would be as torturous as a 4-day fast.
One way to keep things rolling is always having questions to ask friends. Make sure you’re willing to be as vulnerable yourself as you’re asking of them.
Vulnerability cultivates trust between two people and a greater understanding of how we’re all the same in our fears.
22. Would you rather find out for certain that there is a God but, He’s judging us according to the Bible or that we were created by aliens and they’re just observing us like zoo animals?
You’ll find out how jaded they are by religious upbringings and you’ll get a whiff of whether they view extraterrestrial life with fear, fascination, or more likely, a mix of both.
23. Would you rather have magical powers in the normal world and not be able to tell anyone or live in a magical world of your creation but there’s nothing magical about you?
It’s the muggle question.
24. Would you rather work for a boss you hate but make good money, or work for a boss that you love but make minimum wage?
You’ll find out whether they have more fears around practical needs and material gain or their interpersonal relationships.
25. Would you rather be able to see 10 minutes into your future or 10 minutes into the future of someone else?
If they choose the latter, they might really deeply care about someone who is at risk right now.
26. Would you rather, have the entire world think you’re a horrible person but have your family be proud of you; or have the entire world think highly of you but your family thinks you’re a horrible person?
You’ll find out lots about the state of their relationship with their family at the moment.
27. Would you rather change jobs every few years or keep one job for the rest of your life?
How deep are they in the idea of consistency and steadiness? Some people see their steady paychecks as anchors for personal spontaneity. Observe whether you judge them based on their answer and whether your judgment shows your own limited belief system.
When two people are building their relationship, a lot of it involves triggering each other and working through each other’s negative feelings without abandoning the other. It also involves some timely would you rather questions for couples.
28. Would you rather give your partner a cheap and useless gift for every anniversary or an expensive and useful gift that blows all your savings for every anniversary?
Surely there should be some happy medium here…
29. Would you rather date someone famous and have your life scrutinized by the tabloids, or date a regular Joe and have your life judged negatively by everyone close to you and your partner?
We will be judged in life no matter who we are or what we do so we might as well accept it from multiple directions.
30. Would you rather have a family of 12 children or never be able to have children at all?
Is procreating their priority or not?
31. Would you rather have a rich partner who doesn’t love you, but will provide for you for the rest of your life, or a poor partner who loves you, but can’t hold a job long enough to pay for your needs?
There’s a good chance that the person who can’t hold a job long enough to pay for your needs has some personal problems. You’ll find out whether they’re confident in their own finances to make relationship choices outside of them. Either way, this question actually tests whether the person has enough self-love to say “neither.”
32. Would you rather date someone who was intelligent without common sense or someone who had common sense but is not-so-intelligent?
You’ll find out what their personal definition of common sense and intelligence actually entails.
33. Would you rather camp out with your partner with only a small survival kit in a beautiful natural location, or camp out in a comfortable RV in a trailer park without any picturesque views?
You’ll find out whether they value actual nature more than their creature comforts.
34. Would you rather take an exhausting and unenjoyable trip to an exotic location for your honeymoon, or have a relaxing time at a dingy motel along the highway?
You’ll find out how attached they are to the perfect honeymoon societal narrative and whether they are resourceful enough to make something out of nothing.
Check out our list of would you rather questions funny to get a laugh out of your inquiries.
35. Solve the biggest problems facing humanity but live and die alone — or live a hidden life with a deeply satisfying love relationship and meaningful work?
Living and dying alone doesn’t necessarily indicate that you are unloved or that people are ungrateful for you. It can be the result of boundaries that you set for yourself.
36. Lose your looks in a disfiguring accident or suffer brain damage that alters your personality?
Inner or outer damage. That’s the quandary.
37. Have hair that looks great all the time or look as though you’re wearing perfectly-applied make-up even when you’re not wearing any?
This might be a gauge as to whether a person is more insecure about their hair or their face. It could also indicate which one they feel they “have to” work harder at, if either.
38. Would you rather have a boomerang that kills and could find anyone individual of your choice, any place on the planet, but could only be used once or a boomerang that always returns to you with one dollar?
You’ll find out whether they find revenge or steady financial gain a greater asset in their life.
39. Would you wake up each morning to discover that your non-dominant arm has been replaced by an animal appendage or permanently replace your bottom half with an animal bottom of your choice?
One of them indicates a personal choice, the other indicates force.
40. Would you rather hear people’s thoughts or control people’s minds?
Find out how much value this person places on controlling others and consider whether that’s a red flag for whether you want to pursue the friendship further.
Sometimes questions about sex are out of bound. Some would you rather questions clean are appropriate for the event.
41. Would you rather become a sentient strawberry with the mind you have now (no physical ability for mobility or communication) or just become a regular strawberry with strawberry thoughts?
What a great thing to speculate on the kinds of thoughts a regular strawberry has.
42. Would you rather have 50 million dollars or 50 guaranteed healthy youthful looking years added to your life?
Money or guaranteed health? Ultimately one is an illusion, the other is not.
43. Would you rather have infinite money or unending love?
It’s this question over and over and over again in different words. Be sure you don’t sound like a broken record.
44. Would you rather eradicate world rapists or terrorists?
Is there a separation between the two?
45. Would you rather have the details of your financial life or your love life be made public?
Which one holds more inflammatory skeletons in the closet? Which one does the person feel more shame about?
46. Would you rather die of sadness or die of guilt?
Who says either of these things cause death? Sadness is a much broader emotion than guilt.
47. If you were born to a teenager, would you rather be kept or put up for adoption?
What a terribly judgmental thing to assume that a teenager’s ability to mother is not enough because of her age. Using this question in these words will reveal your own limited beliefs.
48. On a long plane ride, would you rather be left alone or would you rather strike up a conversation with your seat partner?
We suppose it would depend heavily on who the seat partner is, but in general, there are introverts and extroverts.
49. Would you rather be able to fly or teleport?
Straightforward super-power question.
50. Would you rather be decent in everything or extremely talented in one thing?
Well-rounded, or downright prodigy? What imagined struggles come up?
Not all questions are easy to answer. It’s important to challenge ourselves emotionally and dare to express the things inside us that are painful to sit with. Check out these hard would you rather questions.
51. Would you rather have indestructible will power or be unquestionably lucky?
This can spurn a conversation about what “unquestionably lucky” means. Further, will power runs out eventually and then the heart must kick in.
52. Would you rather spend the next year exempt from all taxes or have a one month paid vacation?
Money or time?
53. Would you rather it be daytime for the rest of your life or night?
People tend to think daytime people are somehow superior to night-oriented people. But remember that a lot of people gravitate towards the night because the energy is less focused and intense.
54. Would you rather be able to stop time at will or age at half the normal human rate?
There are people out there that are living the latter one. Stopping time at will has a lot to do with how time is an illusion.
55. Would you rather make money off inventing a miracle drug that saves lives, or give it away for free?
This brings up our own financial struggles. When this happens in real life, oftentimes it’s both, not one or the other.
56. Would you rather be a highly paid professional athlete or serve as the president of a prestigious university?
Sports or academics?
When you’re in trusting relationship with someone, you can start asking personal questions.
57. Would you rather be stuck in a cage with a lion or be hung off of a 300ft tall building?
Which one implies certain death or a chance to fight back?
58. Would you rather never have to wait in traffic again for the rest of your life or never get a headache again for the rest of your life?
This probably depends on the severity of the headaches the person has already experienced.
59. Would you rather never be able to go out during the day or never be able to go out during the night?
Does the person accept the options or do they question why you chose such limitations?
Exploring the depths of the mind can be had with philosophical questions about life.
60. Would you rather wake up and find yourself in the middle of a desert or wake up and find yourself in a rowboat in the middle of the ocean?
Is moving water or dehydration scarier?
61. Would you rather be the greatest music composer in the world and have no one listen to your music, or be a super famous musician but be unable to perform any of your music?
Making certain kinds of music is an athletic experience.
62. Would you rather wake up in a random person’s body every year and be in control of their decisions and actions for the whole year or wake up in a random person’s body once a week but without any control over their actions and decisions?
This draws on our fantasies of being someone else for a short time and how that would go. Is it to escape ourselves or to add to our perspectives?
When we start pondering the greater meaning of why we are here, we have existential questions.
63. Would you prefer nobody coming to your wedding or nobody coming to your funeral?
Is death or marriage a more important or laced with more social pressure?
64. Would you rather discover something evil and prevent it or discover something great and spread it?
This is a good one and an indicator of a person’s defensive instincts.
65. Would you rather spend 2 months in a mental asylum or 2 months in jail with dangerous criminals?
That’s a hard choice for sure.
66. If you could change worlds, would you rather have a world with magic in it or a world with no value for money?
Money is a made-up value and there already is magic in the world for those who choose to believe.
67. Would you rather have the power to make people fall in love with you or have the power to make people work on your behalf?
This idea of forcing people to do anything against their will is a scary thing and a person who would simply refuse to answer this low-vibe question is a friend worth keeping.
When all the inane chit-chat is said and done, it’s time for some thought provoking questions.
68. Would you rather be able to forget your own memories or be able to make others forget theirs?
Forgetting is very different from forgiving. That’s a discussion topic worth exploring.
69. Would you rather have a photographic memory or gain an extra 40 IQ points?
How does the person view intelligence and memory?
Downloadable List of Deep Would You Rather Questions
Here is a downloadable list of deep would you rather questions (right click the image and select Save Image As…) :
More Awesome Questions To Ask
Our curated lists of questions do not end here. Check out some additional resources to gain a better understanding of people all around you in every corner of your social circles:
- Make sure you’re versed in deep conversation topics and thinking about how you would answer them too.
- A starter topic actually leads to other topics with these deep conversation starters.
- If you find yourself running out of ideas, check out our interesting conversation topics.
How To Pick Deep Would You Rather Questions
There are a few parameters and things to consider that you need to know about how to pick the right questions for your audience.
Here is how to deep would you rather questions:
1. What you already know
Be mindful not to ask different versions of the same question over and over again. It shows you’re not listening or you’re so self-conscious you’re not really absorbing anything. A more intelligent thing to do would be to recall something the person shared with you in the past and expanding and developing that together.
2. What you’re willing to share
Any inquiries you make of another should be matched with the level of vulnerability you’re willing to offer them in return. Share what you have learned from your mistakes and speak of them with humor that reminds everyone how human you are.
3. Questions reveal things
For example, if most of your questions revolve around money vs. love, it reveals that that’s a dichotomy that you yourself think about often.
The complexity of your deep would you rather questions works sort of similar to lengthening your life.
Throughout history, people have chased the fountain of youth to expand the length of their lives. What if we instead scaled the richness of each passing moment of our lives by cultivating the deepest connections imaginable with our loved ones?
Ask deep would your rather questions, and ask yourself them too, to know them and yourself at the most intimate level.