150 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 150 what-if and hypothetical questions for couples, from goofy to genuinely deep, including sets for your boyfriend or girlfriend and short what-if scenarios to talk through together. 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 scored version? Play the couples quiz and see how well you can guess each other’s answers.
• 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?

Funny and crazy what if questions for couples

11. If you woke up tomorrow as a golden retriever, how long would it take me to notice?
12. What if your most-used emoji replaced your face for a week, which one would we be stuck with?
13. If you came with a warning label, what would it say?
14. What if we were cartoon villains, what would our ridiculous evil plan be?
15. If our home came with a friendly ghost, what house rules would we give it?
16. What if you could only speak in movie quotes for a whole day, which one would you use the most?
17. If a narrator followed you around all day describing everything you did, whose voice would you pick?
18. What if we entered a cooking competition as a team, who gets sent home first, and for what dish?
19. If the zombie apocalypse started tonight, what is your weapon of choice from our kitchen?
20. What if you could pass one ridiculous law that everyone had to follow, what would it be?
21. If you could only eat food of one color for a month, which color are you choosing?
22. What if someone made a movie about our first date, what genre would it be, and who plays us?
23. If you could shrink to the size of a mouse whenever you liked, what would you get up to?
24. What if we could add one completely impractical feature to our home, like a slide, a ball pit, or a secret bookcase door?
25. If animals could vote, which one would win the election, and what would its first policy be?

What if questions for your boyfriend

These work for any partner, whatever your genders, so ask them your way.

26. If you could read my mind for one day, what would you most want to find out?
27. What if we met for the first time today, how would you try to get my attention?
28. If you could keep one of my habits forever and quietly delete another, which ones would you pick?
29. What if you had to cook one meal that sums up how you feel about me, what is on the plate?
30. If you could put one of our inside jokes on a billboard, which one would it be?
31. What if you had a whole weekend with no responsibilities while I was away, how would you spend it?
32. If you had to surprise me tomorrow with something I have mentioned wanting, what would you pick?
33. What if your best friend had to describe us in three words, what would they say?
34. If we swapped daily routines for a week, what do you think would surprise you most about mine?
35. What if you had to plan a date using only places within walking distance of home, where would you take me?

What if questions for your girlfriend

Like the set above, these work for any partner.

36. If I could take one recurring task off your plate forever, which one would you hand over?
37. What if you could design the perfect “just because” surprise for yourself, what would it be? I am taking notes.
38. If we could spend a day inside your favorite book or movie, which one would you choose, and who would we be?
39. What if our relationship had a soundtrack, which song plays when we argue, and which one plays when we make up?
40. If you could take me to one place from your childhood for an hour, where would we go?
41. What if you could see our relationship through my eyes for a day, what do you hope you would see?
42. If you could make one daydream real for a single day, which one would you pick?
43. What if we could only talk to each other through handwritten notes for a week, what would your first note say?
44. If a celebrity had to give us relationship advice, who would you pick, and what do you think they would say?
45. What if we swapped hobbies for a month, which of mine do you think you would secretly love?

Adventure and travel what-ifs

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

Money and lifestyle what-ifs

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

Deep what if questions for couples

66. What if you knew you had exactly one year left, how would you want to spend it?
67. If you could relive one day of your life exactly as it was, which day?
68. What if you could send one message to your younger self, what would it say?
69. If you could know the answer to one question about our future, would you want to, and which?
70. What if you could remove one fear from your life permanently, which one?
71. If you could master any part of yourself overnight, what would you fix?
72. What if you could keep only one memory of us, which would you save?
73. If you could give me one lesson you learned the hard way, what would it be?
74. What if we could add one hour to every day, how should we spend it together?
75. If you could be certain of one thing about us, what would you want it to be?
76. What if I were struggling with something and hiding it from you, how would you want me to tell you?
77. If you could understand one part of my past better, which part would it be?
78. What if we disagreed about one really big life decision, how do you think we should decide?
79. If you could fully forgive yourself for one thing, what would it be?
80. What if you could feel completely understood by me about one thing, what would you choose?
81. If you knew no one would judge you, what is one dream you would finally say out loud?
82. What if you lost everything you own tomorrow, what would still make you feel like you?
83. If you could keep one thing from the way you were raised and let go of another, what would they be?
84. What if you could ask me for one thing without worrying about being a burden, what would you ask for?
85. If you could hear how I talk about you when you are not in the room, what do you hope you would hear?

What if questions about love and relationships

86. What if you could know exactly how I feel about you at any moment, would you want to?
87. If you had to pick the moment you started falling for me, when would it be?
88. What if love came with a user manual, what would the first page of yours say?
89. If one small thing I do for you could happen every single day, what would you choose?
90. What if we could only say “I love you” once a year, how would you make it count?
91. If you could change one thing about how we argue, what would it be?
92. What if we had never met, where do you think you would be right now?
93. If everyone had a little meter showing how loved they feel, what fills yours up fastest?
94. What if you could borrow one habit from a couple we admire, which one would it be?
95. If you could feel exactly how you felt about me in our first month together, just for one day, would you want to?
96. What if you had to describe how I show love without using the word “love,” what would you say?
97. If love languages were real languages, how fluent do you think I am in yours?
98. What if we changed one thing about how we greet each other or say goodbye each day, what should it be?
99. If we could hear each other’s thoughts during our next disagreement, would it help or make it worse?
100. What if you could thank me for one thing I do that I probably do not realize matters, what would it be?

If question 97 starts a friendly debate, settle it with the love languages quiz.

What if scenarios for couples

Short dilemmas to talk through together. There is no right answer, only the one you would choose as a team.

101. We find an envelope full of cash on an empty street, with no name on it. Do we keep it, hand it in, or try to find the owner?
102. One of us is offered a dream job in another country, just as the other’s career is taking off at home. How do we decide?
103. A close friend asks what we honestly think of their new partner, and we both think the partner is bad news. Do we tell the truth, and who does the talking?
104. We win a free week away, but it falls on a family event one of us promised to attend. What do we do?
105. You find out a close friend’s partner is cheating on them. Would you tell your friend, and would you want a friend to tell you?
106. We can move into a bigger, nicer place for the same money, but it adds an hour to both of our commutes. Do we take it?
107. One of us is offered a big raise that comes with a lot more travel and late nights. How much time apart is worth it?
108. A family member asks to move in with us for six months. What would our conditions be, and what would make us say no?
109. We have a free Saturday, and one of us wants a big adventure while the other wants to stay in. How do we make it a good day for both?
110. Someone hands us a generous amount of money on one condition: we have to spend it on an experience together within a month. What do we book?
111. One of us gets the chance to go back to school full time, but money would be tight for two years. Is it worth it?
112. A friend offers us a free puppy, a very energetic one, and we both work long days. Do we say yes?
113. Our phones get locked in a drawer for a full week, no exceptions. What would we miss, and what might we gain?
114. We have the budget for either one big trip this year or several small weekend getaways. Which do we choose?
115. A stranger offers us a large sum of money to not speak to each other for 48 hours while living under the same roof. Do we take it, and how would we cope?

Us-and-the-future what-ifs

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

Would-you-rather hypotheticals

126. Would you rather always know when someone is lying or always get away with lying?
127. Would you rather be able to teleport or to time travel?
128. Would you rather have more time or more money?
129. Would you rather never feel physical pain or never feel embarrassment?
130. Would you rather live without music or without movies?
131. Would you rather always be slightly overdressed or slightly underdressed?
132. Would you rather have a rewind button or a pause button for life?
133. Would you rather be the funniest or the wisest person in the room?
134. Would you rather relive your best day or erase your worst?
135. Would you rather be able to talk to animals or speak every human language?

If these are your favorite kind, we have a full list of 250 would you rather questions for couples, from cute to spicy.

Values-revealing what-ifs

136. What if you had to describe a good life in one sentence, what would you say?
137. If you could be remembered for one thing, what would you want it to be?
138. What if you could instantly heal one relationship in your life, which one?
139. If you could give everyone in the world one quality, what would you choose?
140. What if you had to choose between adventure and security for the next ten years?
141. If you could protect one thing about who you are today, what would it be?
142. What if you could undo one common mistake people make in love, which one?
143. If you could teach one thing in schools, what would it be?
144. What if you had to name the value you would never compromise, what is it?
145. If your life had a motto carved somewhere, what would it read?

Playful closers

146. If we got a joint tattoo (hypothetically), what would it be?
147. What if we had to pick a couple’s catchphrase, what is it?
148. If we were characters in a video game, what would our special powers be?
149. What if we hosted a talk show together, who is the first guest?
150. 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.

Questions you do not know the answer to are also the core of the Roommate Reset. For more games, try never have I ever for couples or these deep conversation starters.