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Questions about hypotheticals
13 hand-curated question banks on hypotheticals, each tailored to a specific relationship. What you ask your mom isn't what you ask your best friend.
A few questions from these sets
- Best friend If you could relive one year of your life knowing what you know now, which year?
- Boyfriend If you could erase one memory of yours forever, would you, and which?
- Coworker If you could have any other job in this company for a week, whose chair do you steal?
- Crush Would you rather your life be interesting or peaceful, if you genuinely had to pick one?
- Daughter If you had been handed this household's money for a month at fifteen, what would you have paid for that we did not?
- Friend You can know the exact day you'll die or the cause, but only one. Which do you want, and which would you refuse?
- Girlfriend Would you rather know exactly how your life turns out or be surprised by all of it?
- Grandpa If I turned up in your first year of working life, what would nobody have had to explain to me — and what would I never have worked out?
- Kid If you could make one rule that everyone in the whole world had to follow, what would it be?
- Mom If you had been paid the going rate for everything you did here, what would have been on the first invoice that we would have argued about?
- Partner If we suddenly won enough money to never work again, what would you actually do with your days?
- Sibling If you had to give up either music or the ability to travel forever, which goes?
- Son If aliens landed and picked one person from this family to explain humanity to them, who are they picking and why?
- Best friend
30 Hypothetical Questions to Ask Your Best Friend
30 hypothetical questions for your best friend — would-you-rather and what-if scenarios that turn a normal night into one you both remember.
- Boyfriend
30 Hypothetical Questions to Ask Your Boyfriend
30 hypothetical questions to ask your boyfriend — would-you-rather and what-if scenarios that reveal how he actually thinks.
- Coworker
50 Hypothetical Questions to Ask a Coworker
50 light, workplace-safe hypothetical questions for a coworker — what-ifs that break the ice without crossing a single professional line.
- Crush
50 Hypothetical Questions to Ask Your Crush
50 hand-curated questions to ask your crush about what-ifs — built to skip the small talk and get to the answers that actually matter.
- Daughter
50 Hypothetical Questions to Ask Your Daughter
50 hypothetical questions to ask your daughter — what-ifs that move her out of the daughter's seat, where she answers with your face already in the room.
- Friend
30 Hypothetical Questions to Ask a Friend
30 hypothetical questions to ask a friend — what-ifs and would-you-rathers that look like a game and quietly reveal what someone values and fears.
- Girlfriend
50 Hypothetical Questions to Ask Your Girlfriend
50 hypothetical questions to ask your girlfriend — playful what-ifs and would-you-rathers that quietly reveal how she thinks, dreams, and decides.
- Grandpa
50 Hypothetical Questions to Ask Your Grandpa
50 hypothetical questions to ask your grandpa — what-ifs that let a man with a whole life behind him weigh it against the ones he never lived.
- Kid
30 Fun What-If Questions to Ask Your Kid
30 playful what-if and would-you-rather questions to ask your kid — silly, imaginative scenarios that quietly reveal how their mind and their heart work.
- Mom
50 Hypothetical Questions to Ask Your Mom
50 hypothetical questions to ask your mom — what-ifs that reach the woman who existed before the role, and the arrangements nobody ever put to her.
- Partner
30 Hypothetical Questions to Ask Your Partner
30 hypothetical questions to ask your partner — playful what-ifs and would-you-rathers that quietly surface the values you'll build a life on.
- Sibling
50 Hypothetical Questions to Ask Your Sibling
50 hypothetical questions to ask your sibling — would-you-rathers and what-ifs that turn a normal evening into the kind of argument only family can have.
- Son
50 Hypothetical Questions to Ask Your Son
50 hypothetical questions to ask your son — what-ifs that get a straight answer out of a boy, or a grown man, who edits everything else for you.