These 60 philosophical questions cover the self and free will, happiness and death, right and wrong, society and love, and God and knowledge. The last ten are lighter. Pick one you don’t already have an argument ready for.
The classic puzzle behind each group
Many of these questions are old problems in everyday words. Knowing the name helps if you want to read further after the conversation.
- Identity, mind and free will (1 to 10). Question 3 is the Ship of Theseus: if a ship’s planks are replaced one at a time until none of the originals are left, is it still the same ship? Question 8 echoes John Searle’s Chinese Room argument from 1980, which says following rules for symbols is not the same as understanding them.
- Happiness, meaning and death (11 to 20). Question 12 is Robert Nozick’s experience machine, from his 1974 book Anarchy, State, and Utopia. Questions 19 and 20 come from Epicurus, who argued that death can’t harm us because we aren’t there to experience it, and Lucretius, who compared the time after death with the time before birth.
- Right and wrong (21 to 30). Question 21 retells the Ring of Gyges from Plato’s Republic, where the ring’s power of invisibility is used to argue that most people would act unjustly if they could never be caught. Question 25 is Peter Singer’s drowning child, from his 1972 essay “Famine, Affluence, and Morality.”
- Society, love and beauty (31 to 40). Question 31 is John Rawls’s veil of ignorance: choose the rules for a society without knowing where you’ll end up in it. Question 36 uses Aristotle’s three kinds of friendship, based on usefulness, pleasure or character.
- God, truth and knowledge (41 to 50). Question 42 echoes Descartes, who imagined a powerful deceiver misleading him in order to find which beliefs could survive any doubt.
The lighter group needs no background. It’s a good place to start with mixed company or teenagers.
Turn an opinion into a discussion
Suppose someone answers question 21 by saying they’d behave exactly the same. Ask for a case: would they read a private letter left open on a table? Take a free seat at a concert? A concrete example tests the idea without arguing over definitions.
Try one follow-up at a time. If you disagree, name the exact point where your reasoning parts ways. Before you argue against a view, state it in its strongest form, then check that the other person agrees with your summary. Don’t keep changing the hypothetical until they give the answer you wanted.
“I haven’t thought about that” is a fine answer. Give the person time, or come back to the question later. If one of you tends to speak faster, you can each write an answer first.
When an idea leads to a story
Philosophical questions often lead somewhere personal. If a parent says their view of success changed after their first job, ask about that job: who hired them, what the work was like, and which moment they still remember. Our family interview guide can help you follow that thread. With their permission, save the story and its context rather than a single line about their philosophy.
For questions about your own life rather than ideas about life in general, try existential questions or deep questions. For a portrait of someone’s tastes and values, try the Proust Questionnaire and family adaptation.