These 40 thought provoking questions are about the world rather than your inner life: technology, how society works, work and money, and history. None needs a confession or a correct answer. Each one rewards a guess, a reason and a second look.
Guess before you look it up
Several questions invite a quick search. Try answering first. A table of people guessing why time seems to speed up with age, or what a town for 75-year-olds would need, usually has a better conversation than one reading out a search result. Look it up afterward if you’re curious.
Ask for reasons, not only answers. “Why do you think that?” and “What would someone who disagrees say?” keep a question going longer than another question would.
Ask someone who was there
Questions 1 to 10, 28 and 31 to 33 work especially well with older relatives. A grandparent who remembers the first television in the house, or a parent who learned to type on a typewriter, has seen change that younger people have only read about. Ask for one specific day: where they were, who else was there and what they thought at the time. If the story is worth keeping, our questions for grandparents go further.
Choosing a different kind of question
For questions about your own feelings and relationships, use deep questions. For classic puzzles such as free will and the meaning of life, use philosophical questions. For issues where people take sides, such as how technology should be regulated, use controversial questions.