40 Hypothetical Conversation Questions

Hypothetical conversation questions are a fantastic way to practice speaking English. Engaging in hypothetical scenarios encourages creative thinking, problem-solving, and exploring imaginative ideas—which means you’ll be having fun while you improve your English.

In this blog post, we’ve listed a collection of fun hypothetical conversation questions tailored for ESL learners.

As you work your way through this list, remember: hypothetical questions involve hypothetical or conditional situations. To answer these questions effectively, you’ll need to use conditional verb forms such as “would,” “could,” “might,” and “should” to indicate that you are discussing a hypothetical scenario.

Hypothetical Conversation Questions

1. If you could travel back in time, which historical event would you want to witness?
2. Imagine you had the power of invisibility for a day. What would you do?
3. If you could visit any place in the universe, where would you go?
4. Suppose you woke up with the ability to speak any language fluently. Which language would you choose?
5. If you could have a conversation with any fictional character, who would it be and why?
6. Imagine you could eliminate one global issue. What would you choose?
7. If you were to write a book, what genre would it be and what would it be about?
8. Suppose you could possess a talent you currently lack. What would it be?
9. If you could redesign your city, what changes would you make?
10. Imagine you had the ability to communicate with animals. Which animal would you talk to first?
11. If you could time-travel to the future, what would you want to see?
12. Suppose you were given a magic power for a day. What would you do with it?
13. If you could switch lives with someone for a week, who would it be?
14. Imagine you could solve one world problem. What would you choose?
15. Suppose you were in a different profession. What would it be?
16. If you could change one law, what would it be and why?
17. Imagine you could relive any day of your life. Which day would you choose?
18. Suppose you were the leader of your country. What changes would you implement?
19. If you could have dinner with any historical figure, who would it be?
20. Imagine you were a character in a book. What type of story would it be?
21. If you could travel anywhere in time, past or future, where and when would you go?
22. Imagine you could instantly learn any skill. What skill would you choose and why?
23. If you could have a conversation with a famous historical figure, who would it be and what would you ask them?
24. Suppose you could become a character from a book or movie for a day. Who would you choose and what would you do?
25. If you woke up with the ability to speak to animals, which animal would you talk to first and what would you ask?
26. Imagine you discovered a new planet. What would you name it and who would you invite to explore it with you?
27. If you had the power to solve one global problem, what issue would you address and how?
28. Suppose you could live in any era of history. Which era would you choose and why?
29. If you could design a new mode of transportation, what would it be and how would it work?
30. Imagine you could switch lives with someone for a week. Who would you choose and what experiences would you gain?
31. If you found a magic key that could open any door, where would you use it to go?
32. Suppose you could be a character in your favorite video game. What game would it be and what role would you play?
33. If you were given the power of telekinesis (moving objects with your mind), how would you use it?
34. Imagine you could create a new holiday. What would it be called and how would people celebrate it?
35. If you could spend a day with any fictional character, who would it be and what adventures would you have?
36. Suppose you could become an expert in any field overnight. What field of expertise would you choose?
37. If you could redesign your school or workplace, what changes would you make to create a better environment?
38. Imagine you could talk to plants. What would you ask them and what secrets might they reveal?
39. If you were a character in a fantasy world, what magical power or ability would you possess?
40. Suppose you could solve a mystery from history. Which mystery would you choose to solve and why?

Hypothetical scenarios allow us to step into different shoes and expand our understanding of the world. But hypothetical conversation questions require the use of advanced grammatical techniques, so they’re best for intermediate and advanced ESL learners.

If these questions were a little too complicated for you and your speaking partner, check out the other ESL Discussion Topics and ESL conversation questions on our site.