80 Unique Hypothetical Questions to Start a Conversation

Starting a conversation can sometimes feel like a challenge, especially when you want it to be engaging and memorable. Hypothetical questions are a fantastic way to break the ice and dive into thought-provoking discussions. They allow you to explore various scenarios and reveal your imagination, values, and personality.

Whether you’re getting to know someone new or simply looking to spark an interesting chat, these 80 unique hypothetical questions will keep the conversation flowing and enjoyable.

Imaginative and Fun

1. If you could live in any fictional world, where would you choose to go?
2. What would you do if you could be invisible for a day?
3. If you could have dinner with any three historical figures, who would they be?
4. What would happen if you woke up one day with the ability to speak any language fluently?
5. If you could teleport anywhere in the world right now, where would you go?
6. What would you do if you could time travel to any era for a day?
7. If you had the power to read minds, whose thoughts would you listen to first?
8. What would you do if you suddenly found yourself in the body of your favorite animal?
9. If you could relive one day of your life, which day would you choose?
10. What would you do if you could switch lives with someone for a week?

Deep and Thought-Provoking

11. If you could change one decision in your past, what would it be and why?
12. What would you do if you knew today was your last day on Earth?
13. If you had the chance to solve one global issue, which one would you tackle?
14. What would you do if you could ask one person, living or dead, any question and get a truthful answer?
15. If you could change one law in your country, what would it be?
16. What would you do if you could know the exact moment and manner of your death?
17. If you could bring back one extinct species, which would you choose?
18. What would happen if you suddenly had the ability to change one thing about the world?
19. If you could live forever, would you choose to, and why or why not?
20. What would you do if you had the power to erase one memory from your past?

Adventurous and Bold

21. If you could go on a space mission to another planet, would you do it?
22. What would you do if you were given a one-way ticket to anywhere in the world?
23. If you could master any skill instantly, which one would you choose?
24. What would you do if you were offered the opportunity to climb the highest mountain in the world?
25. If you had to pick between being a famous explorer or a renowned scientist, which would you choose?
26. What would happen if you had the chance to swim with great white sharks?
27. If you could go on an adventure with any fictional character, who would it be?
28. What would you do if you were given the chance to dive to the deepest part of the ocean?
29. If you could survive in any extreme environment, which one would you choose to explore?
30. What would you do if you were offered the chance to live in a remote location with no technology for a year?

Playful and Light-Hearted

31. If you could only eat one type of cuisine for the rest of your life, what would it be?
32. What would you do if you could instantly learn any dance style perfectly?
33. If you could spend a day as any animal, which one would you choose?
34. What would happen if you could control the weather for a week?
35. If you had the power to change your name, what would you choose?
36. What would you do if you could have any superpower for 24 hours?
37. If you could switch wardrobes with any celebrity, whose style would you steal?
38. What would you do if you could swap places with your best friend for a day?
39. If you could live in any decade from the past century, which one would it be?
40. What would happen if you could bring any fictional character to life for a day?

Romantic and Dreamy

41. If you could plan the perfect date without any limitations, what would it look like?
42. What would you do if you could spend a weekend anywhere in the world with your significant other?
43. If you could write a love letter to anyone, who would it be and why?
44. What would happen if you could relive your first kiss with someone special?
45. If you could take your partner on a surprise trip, where would you go?
46. What would you do if you could create the ultimate romantic movie scene in real life?
47. If you could live out one romantic fantasy, what would it be?
48. What would happen if you had the chance to dance under the stars with your crush?
49. If you could create your own romantic holiday, what traditions would it include?
50. What would you do if you could plan a dream wedding without any budget constraints?

Curious and Quirky

51. If you could talk to any animal, which one would you choose and what would you ask?
52. What would you do if you found out you could breathe underwater?
53. If you could visit any place in the universe, real or fictional, where would you go?
54. What would happen if you could live in any historical period for a week?
55. If you could swap lives with anyone for a day, who would it be and why?
56. What would you do if you suddenly had the ability to see into the future?
57. If you could choose to be any mythological creature, which one would you pick?
58. What would happen if you could shrink down to the size of an insect for a day?
59. If you could live in any house from a movie or TV show, which one would it be?
60. What would you do if you could travel back to any event in history to witness it firsthand?

Whimsical and Magical

61. If you could cast any spell, what would it be and why?
62. What would you do if you discovered you had the ability to fly?
63. If you could have any magical creature as a pet, which one would you choose?
64. What would happen if you found a door that led to a magical world?
65. If you could have any fairy tale come true in your life, which one would it be?
66. What would you do if you could make any wish come true right now?
67. If you could attend any fictional school, which one would it be and why?
68. What would happen if you could turn invisible anytime you wanted?
69. If you could have a conversation with a ghost, who would you want to talk to?
70. What would you do if you discovered you had the power to control time?

Thoughtful and Reflective

71. If you could erase one bad habit from your life, what would it be?
72. What would you do if you had the chance to see your life in 10 years?
73. If you could relive one moment in your life without changing it, which one would it be?
74. What would happen if you could spend a day in the life of your future self?
75. If you could ask your future self one question, what would it be?
76. What would you do if you were given the power to change one event in history?
77. If you could know the outcome of one decision before making it, would you want to?
78. What would happen if you could revisit your childhood for a day?
79. If you could spend a day with your younger self, what advice would you give?
80. What would you do if you had the power to change one thing about yourself instantly?

Why Hypothetical Questions Make Great Conversation Starters

Hypothetical questions are a powerful way to start conversations because they encourage people to think creatively and share parts of themselves they might not reveal through ordinary small talk. These questions allow for open-ended answers, sparking discussions that can go in many different directions. Whether you’re trying to break the ice with someone new or deepen your connection with a friend or partner, hypothetical questions offer a chance to explore shared interests, values, and fantasies in a fun, low-pressure way.

By discussing imaginative scenarios, you also get to see how the other person thinks and what they value, which can lead to deeper understanding and more meaningful conversations. Plus, the playful nature of these questions keeps the conversation light and enjoyable, making it easier to connect with others on a personal level.

Next time you find yourself in a conversation rut or just want to keep things interesting, try out a few of these hypothetical questions. You might be surprised at where the conversation leads and how much you can learn about someone with a simple “what if.”