These 40 hypothetical questions are what-ifs that could almost happen: a free year, a move to a new city, a new career, an extra day each week. Because they’re close to real life, the answers often show what someone wants but hasn’t said.
Getting past the first answer
The first answer to a hypothetical is usually the obvious one. Ask “Why that one?” or change one detail, such as “What if you had to go alone?” The real preference tends to show up in the second answer.
The last follow-up, “What’s stopping you from doing a smaller version now?”, is the one that turns a game into a plan. Use it gently. Some people want to dream without being pushed.
Questions for family
Questions 10 and 40 ask about parents and grandparents. They work well with older relatives, who can tell you what that day or that dinner might have been like. If the answer turns into a story, our questions for grandparents can take it further.
For absurd what-ifs, such as talking furniture or a moon made of cheese, see weird questions. For quick choices between two options, try would you rather questions.