75 What If and Hypothetical Questions for Couples

Hypothetical questions are a shortcut to the good stuff. A silly “would you rather” loosens everyone up, and a well-placed “what would you do if…” can reveal more about someone’s values than an hour of serious talk. Because they are just pretend, they feel safe, which is exactly why they work.

Here are 75 what-if and hypothetical questions for couples, from goofy to genuinely deep. Use them on a date night, a road trip, or a slow evening on the couch.

How to play

• Both of you answer. Guessing the other’s answer first makes it even more fun.
• No wrong answers. The point is to explore, not to score.
• Let the follow-up questions happen. “Wait, why that?” is where it gets interesting.
• Want a prompt without thinking, pick a daily question in the PumPum relationship app and riff from there.

These pair perfectly with the fun half of the Weekly Care layer of your Couple Care Routine.

Silly what-ifs (warm up)

1. If you could have any superpower, but only a slightly useless version, what would it be?
2. If we were a two-person band, what would we be called?
3. If you could turn any food into a zero-calorie health food, which one?
4. If our pets could talk for one day, what would they say about us?
5. If you had to eat one meal for the rest of your life, what is it?
6. If we swapped bodies for a day, what is the first thing you would do?
7. If you could instantly master one instrument, which one?
8. If our life were a sitcom, what would the theme song be?
9. If you could have dinner with any fictional character, who?
10. If you could rename yourself, what name would you pick?

Adventure and travel what-ifs

11. If we could live anywhere in the world for a year, all expenses paid, where?
12. If you had to pick one country to explore for a whole month, where?
13. What if we could only ever travel by one method for life: road trip, train, boat, or plane?
14. If we won a surprise weekend trip tomorrow, where do you hope it is?
15. If you could relive one trip we have taken, which one?
16. What if we had to move to a brand new city next month, how would you want to choose it?
17. If you could see one wonder of the world tomorrow, which?
18. What if we could go back to any decade to visit, which one?
19. If we could take a year-long sabbatical, what would we do with it?
20. If you could wake up fluent in one language, which and why?

Money and lifestyle what-ifs

21. If we won a modest lottery, enough to change things but not retire, what would we do first?
22. What if we had to live on half our income, what would we cut and what would we protect?
23. If money were no object, what would your ideal ordinary Tuesday look like?
24. What if you could only work four months a year, how would you spend the rest?
25. If we could design our dream home, what is the one non-negotiable room?
26. What if we had to give away half of everything we own, how would we choose?
27. If you could invest in our future in one way this year, what would it be?
28. What if we could freeze our expenses forever at today’s prices, would you?
29. If we could fund one dream for someone we love, whose and what?
30. What if we could only keep five possessions each, what makes your list?

Deeper hypotheticals

31. What if you knew you had exactly one year left, how would you want to spend it?
32. If you could relive one day of your life exactly as it was, which day?
33. What if you could send one message to your younger self, what would it say?
34. If you could know the answer to one question about our future, would you want to, and which?
35. What if you could remove one fear from your life permanently, which one?
36. If you could master any part of yourself overnight, what would you fix?
37. What if you could keep only one memory of us, which would you save?
38. If you could give me one lesson you learned the hard way, what would it be?
39. What if we could add one hour to every day, how should we spend it together?
40. If you could be certain of one thing about us, what would you want it to be?

Us-and-the-future what-ifs

41. If we wrote our story as a book, what would this current chapter be called?
42. What if we made one big brave change this year, what should it be?
43. If you could plan our perfect anniversary with no limits, what happens?
44. What if we started a tiny business together, what would it be?
45. If we could pick up a shared hobby and actually stick to it, which one?
46. What if we could design our ideal week from scratch, what does it include?
47. If you could guarantee one tradition lasts our whole lives, which one?
48. What if we could relive our first year together knowing what we know now, what would we do differently?
49. If we could give our future kids or younger relatives one piece of advice, what?
50. What if we grow old exactly as we hope, what does a perfect quiet day look like?

Would-you-rather hypotheticals

51. Would you rather always know when someone is lying or always get away with lying?
52. Would you rather be able to teleport or to time travel?
53. Would you rather have more time or more money?
54. Would you rather never feel physical pain or never feel embarrassment?
55. Would you rather live without music or without movies?
56. Would you rather always be slightly overdressed or slightly underdressed?
57. Would you rather have a rewind button or a pause button for life?
58. Would you rather be the funniest or the wisest person in the room?
59. Would you rather relive your best day or erase your worst?
60. Would you rather be able to talk to animals or speak every human language?

Values-revealing what-ifs

61. What if you had to describe a good life in one sentence, what would you say?
62. If you could be remembered for one thing, what would you want it to be?
63. What if you could instantly heal one relationship in your life, which one?
64. If you could give everyone in the world one quality, what would you choose?
65. What if you had to choose between adventure and security for the next ten years?
66. If you could protect one thing about who you are today, what would it be?
67. What if you could undo one common mistake people make in love, which one?
68. If you could teach one thing in schools, what would it be?
69. What if you had to name the value you would never compromise, what is it?
70. If your life had a motto carved somewhere, what would it read?

Playful closers

71. If we got a joint tattoo (hypothetically), what would it be?
72. What if we had to pick a couple’s catchphrase, what is it?
73. If we were characters in a video game, what would our special powers be?
74. What if we hosted a talk show together, who is the first guest?
75. If our love had a flavor, a color, and a song, what would they be?

Common questions

What is the difference between what-if and would-you-rather questions?

What-if questions are open-ended and invite a story or an opinion. Would-you-rather questions force a choice between two options, which makes them faster and often funnier. Mixing both keeps the conversation lively.

When are these best to use?

Any low-pressure moment: a long drive, dinner, a lazy Sunday, or the fun half of your weekly check-in. Start silly, then let a couple of the deeper ones sneak in once you are both relaxed.

Final note

Pretend questions have a way of telling the truth. Keep a handful of these ready for the next quiet evening, and let one small “what if” open a door you did not know was there.