A Library of Questions

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    Arthur Aron's famous "36 Questions" study demonstrated that escalating, vulnerable, self-disclosing questions can create profound closeness between strangers—sometimes within a single hour (Aron et al., 1997). The mechanism is reciprocal vulnerability: when one person reveals something genuine and the other receives it without judgment, both brains register the other as someone safe and significant. The same mechanism applies, with even more force, to long-term partners.

    The reason most couples stop feeling close after years together is not that they know everything about each other. It is that they have stopped asking anything that risks a real answer. Logistics, venting, and planning fill the available conversational space, and the questions that once made the relationship feel alive quietly disappear.

    This resource is a single-purpose catalog: questions to ask each other. It is not a list of activities, dates, or rituals—those belong to other resources. Every item below exists for one reason: to give the relationship a doorway into a conversation it would not otherwise have.

    How to Use This Library

    Pick one question per week. Ask it during a walk, a drive, a meal, or a quiet evening with no screens. Listen fully. Ask one genuine follow-up question before sharing your own answer—the follow-up matters more than the question itself. The goal is not to get through the list. The goal is to make a habit of being curious about a person you already think you know.

    Why This Matters

    Intimacy is not built by knowing each other's preferences. It is built by being witnessed in the parts of yourself that are still in motion. A real question, asked with real attention, is one of the most loving things a person can offer—and one of the cheapest, most renewable resources in a long-term relationship.

    Light Openers

    • What is something that made you laugh out loud this week?
    • If you had a completely free day tomorrow with no obligations, how would you actually spend it?
    • What is a small thing I do that you genuinely appreciate but maybe have not told me about?
    • What is a song you have been returning to lately, and why?
    • What is the best meal you have eaten in the last month?
    • What is something you are looking forward to that you have not told me about?
    • If you could spend an afternoon with anyone alive, who would it be and what would you do?
    • What is a tiny luxury that feels disproportionately good to you?
    • What is something that made you feel like a kid again recently?
    • What is the last thing that surprised you about yourself?
    • What is the most useless skill you wish you had?
    • What is a place you have never been that you think about often?
    • What is a smell that instantly takes you somewhere?
    • What is something you secretly find beautiful that most people overlook?
    • What is the kindest thing a stranger has ever done for you?
    • What is the best thing that happened to you today, no matter how small?
    • What is a snack you would defend in court?
    • What is the last thing that made you genuinely curious?
    • What is a chore you secretly enjoy?
    • What is a piece of clothing in your closet you love and never wear?
    • What is the most beautiful sentence you have read or heard recently?
    • What is something you have been overthinking lately?
    • What is a small ritual that makes your week feel like your own?
    • What is something you would happily do for free?
    • If today had a title, what would it be?
    • What is a season you wish lasted twice as long?
    • What is the last thing you took a picture of, and why?
    • What is a sound you find unreasonably comforting?
    • What is something on your to-do list that you are quietly enjoying avoiding?
    • What is a small thing in our home that makes you happy every time you notice it?

    Getting to Know You Better

    • What is something you used to believe strongly that you no longer believe?
    • When was the last time you felt truly proud of yourself, and why?
    • What is a part of yourself you do not show many people—and why not?
    • What is a memory from your childhood that still shapes how you respond to things today?
    • Who in your family of origin do you most resemble, and how do you feel about that?
    • What is a compliment you have received that you still think about?
    • What is something you wanted as a child that you finally have now—and what is something you wanted that you have let go of?
    • What is a friendship that shaped you more than the other person probably realized?
    • What is a time you were genuinely afraid, and what got you through it?
    • What is something you do not understand about yourself yet?
    • When do you feel most like yourself?
    • What is a season of your life you would not want to repeat but would not trade either?
    • What is a role you play for other people that you sometimes resent?
    • What is a piece of advice you have ignored your whole life that you might finally be ready to take?
    • What is a teacher, coach, or mentor whose voice still lives in your head?
    • What is something you are good at that you almost never get credit for?
    • What is a stage of your life you romanticize that probably was not as good as you remember?
    • What is something you do that you have never really questioned but probably should?
    • What is the first thing you remember really wanting badly as a child?
    • What is a value you grew up with that you have kept—and one you have deliberately let go of?
    • What is a moment you can point to where you became more yourself?
    • What is a job or role you have always been quietly curious about?
    • Where do you think you are still living out somebody else's expectations?
    • What is something you have outgrown but have not made room to grieve?
    • What is a question you wish someone would ask you more often?
    • What did you think love was when you were sixteen, and how has that changed?
    • What is a part of your story you usually leave out when telling it?
    • What is something about your inner life that would surprise the people who think they know you best?

    Vulnerable and Honest

    • What is something you are afraid of right now that you have not said out loud?
    • What is a regret you carry that you do not usually talk about?
    • What is something you wish someone had said to you when you were younger?
    • When do you feel most alone, even when you are not actually alone?
    • What is a way you have changed in the last few years that you are not sure I have noticed?
    • What is a need of yours that you find it hardest to ask for?
    • What is something you are quietly grieving right now?
    • Where in your life do you feel most stuck?
    • What is something you want to forgive yourself for?
    • What is a story you tell about yourself that may not be true anymore?
    • When was the last time you cried, and what was it really about?
    • What is something you hope I never find out about you—and could you imagine telling me anyway?
    • What is a fear about getting older that you do not usually let yourself look at?
    • What part of you do you wish was easier to love?
    • What is something you are pretending not to need?
    • Where in your life are you performing instead of living?
    • What is a compliment that, if I gave it to you tonight, would actually land?
    • What is a fear you carry about me that you have never said out loud?
    • What is something you want to be told more often, even if it feels embarrassing to ask for?
    • What is a hard truth about yourself you have been circling but not quite facing?
    • When was the last time you felt small, and what made it feel that way?
    • What is something you are carrying alone that you wish you could put down?
    • What is a moment from this year that you have not fully processed yet?
    • What is something you are quietly proud of that you have not shared with anyone?
    • What is a way I could love you better in this exact season of your life?
    • What is a hope you have for yourself that you are almost too superstitious to say?

    About Us

    • When do you feel most loved by me? When do you feel most distant from me?
    • What is something I have done in our relationship that meant more to you than I probably realized?
    • What is something you wish I asked you about more often?
    • If our relationship had a "weather report" right now, what would it be—and why?
    • What is a way I have grown since we have been together that you have noticed?
    • What would help you feel more known by me?
    • What is a small thing I could do this week that would mean a lot?
    • When have you felt closest to me—and what was happening?
    • What is something we do well as a couple that I might be taking for granted?
    • What is a habit between us you would like to keep forever?
    • What is a habit between us you would like to break?
    • When you are quiet, what are you usually thinking about?
    • What is something you have always wanted to tell me but never quite found the moment for?
    • What is a way I have surprised you over time—for better or worse?
    • What is a memory of us you replay when you are away from me?
    • What is one thing we have never talked about that you think we should?
    • What is a version of our relationship you used to dream about that we have actually become?
    • What is a version of our relationship you used to dream about that we have not yet become?
    • What is something I do that you find genuinely attractive that I probably do not realize?
    • What is a moment with me that, looking back, you wish you could relive exactly?
    • What is something we are doing together right now that you hope we never stop doing?
    • When you brag about me to someone, what do you actually say?
    • What is a small inside joke between us that you love?
    • When you picture us at our best, what are we doing?
    • What is a way we are different from other couples we know, in a way that you actually like?
    • What is something you wish we celebrated about ourselves more often?
    • What is a way you have let me see you that you have not let anyone else see?
    • If our relationship were a place, what place would it be right now?

    How We Handle Things Together

    • How do you want me to respond when you are stressed—do you want me to fix, listen, distract, or hold?
    • What does support look like for you on a hard day, in concrete terms?
    • When we disagree, what do I do that helps—and what do I do that makes it worse?
    • How do you know when I am pulling away, and what do you wish I would do instead?
    • What is a topic between us that always seems to escalate—and what do you think we are each really protecting?
    • What is something I do that you have learned to live with but secretly wish was different?
    • What is something you do that you wish I would just name when it bothers me?
    • How do you want to repair after a fight—what makes it actually feel resolved for you?
    • What is a need of yours I am not currently meeting that you have stopped asking about?
    • What does "feeling safe" with me actually look like in day-to-day terms?
    • What is one thing about how we handle money, time, or family that you wish we could re-design?
    • When have you felt most heard by me in a hard moment?
    • What is a fight we keep having that is actually about something deeper, and what is that deeper thing?
    • What is something I do during a hard conversation that you would like me to do less of?
    • What is something I do during a hard conversation that you would like me to do more of?
    • When you are overwhelmed, do you want me closer, further away, or quieter beside you?
    • What is a topic you have been avoiding bringing up—and what would make it safer to bring up?
    • When you imagine us handling a real crisis well together, what does that actually look like?
    • What is something my family of origin patterns do that you can feel showing up between us?
    • What is something your family of origin patterns do that you can feel showing up between us?
    • How do you want me to handle it when you go quiet?
    • What is one thing about how we divide labor at home you would change tomorrow if you could?
    • What is a stress you carry alone that you wish I would help carry?
    • When we are both depleted, what is our best fallback plan—do we have one?
    • How do you want me to respond when you are wrong about something?
    • How do you want me to respond when I am wrong about something?

    Memory and Story

    • What is your favorite memory of us in the first year we were together?
    • What is a moment from our history that you think about more than I would guess?
    • What is a story about your own life you have never told me?
    • What is a story about your parents or grandparents that shaped you without you realizing it?
    • What is a place you would want to revisit together, and why that place?
    • What is a song that, if it came on, would always make you think of me?
    • What is a photograph of us you wish was framed somewhere in our home?
    • What is a small thing from our early days you miss—and could we bring it back?
    • If you wrote the chapter headings of our relationship so far, what would they be?
    • What is a tradition from your family you would want to bring into ours?
    • What is a memory of your own childhood you most want to give to any child we raise—or any niece, nephew, or godchild in our life?
    • What is a moment from our relationship that you would describe as a turning point that I might not see the same way?
    • What is a season of us you were quietly struggling in that I might not have noticed?
    • What is a season of us you look back on as one of the best, and why?
    • What is the first moment you remember thinking, "I could really love this person"?
    • What is the first moment you remember thinking, "this is actually working"?
    • What is a memory of your grandparents or great-grandparents that you do not want to lose?
    • What is a story your family tells about you that you have complicated feelings about?
    • What is a place from your childhood you wish you could walk me through?
    • What is a meal from your childhood that I have never made for you that you would love me to try?
    • What is a "small" memory of us—a totally ordinary day—that has stayed with you?
    • What is a memory you wish we had taken a photograph of and did not?
    • What is something we used to do early on that we could pick back up tomorrow with almost no effort?

    Imagining the Future

    • When you imagine us in ten years, what does the day-to-day actually look like? What is different?
    • What do you want to be remembered for—and are you living in a way that points there?
    • What is a tradition or ritual you would like us to start that we do not have yet?
    • If you could redesign one part of our life together, what would you change first?
    • What would it look like for our relationship to be a place where you become more of who you actually want to be?
    • What is a dream of yours that you have not told me about because it feels too big or too small?
    • What is something you want us to have done together by the time we are old?
    • Where do you want to live in five years—really?
    • What does "a good life" look like to you now, and how is that different from what it used to look like?
    • What is a fear about the future you would like me to know about?
    • If we could spend one month a year somewhere else, where would you want it to be?
    • What is a value you want our life to revolve around more clearly than it does now?
    • What is one thing you hope is still true about us in twenty years?
    • What is one thing you hope is different about us in twenty years?
    • If we had to build a five-year plan from scratch tonight, what would the headline be?
    • What is a "someday" of yours that you would like to make a "this year"?
    • What is a way you want to age that you do not see modeled around you?
    • What does retirement look like to you, honestly?
    • What is a way you hope I will change, and what is a way you hope I will stay exactly the same?
    • What is a legacy—small or large—that you want us to leave behind?
    • What is something we could start now that would compound beautifully over a decade?
    • If we could only commit to one shared goal for the next year, what should it be?
    • What is the shape of an ordinary Tuesday in five years that would make you feel like we did this right?
    • What is a hard conversation we will probably need to have in the next year that we could start having now?

    Playful and Off the Beaten Path

    • If you had to pick a soundtrack for the last year of your life, what three songs would be on it?
    • What is a fictional character you secretly identify with more than you should admit?
    • If you could master one skill overnight, which one—and what would you do with it the next morning?
    • If you were given a small, mysterious cabin in any landscape on earth, what landscape would you pick?
    • What is the most overrated thing you can think of, and what is the most underrated?
    • If your life right now had a theme song, what would it be—and what do you wish it was?
    • If you had to be famous for something, what would it be?
    • What is a meal you would want as your last?
    • What is the strangest compliment you have ever received?
    • If you could give your younger self one specific piece of advice, what would it be?
    • What animal do you think you most resemble in spirit?
    • If you had to switch jobs with a stranger for a week, what job would you secretly hope you got?
    • If you could only keep five photographs from your entire life, what scenes would you want them to be of?
    • If you had to start a tiny absurd business tomorrow, what would it be?
    • If your personality were a sandwich, what would be in it and what would be on the side?
    • What is the worst-named restaurant you can invent right now?
    • If you were a ghost haunting one room in any house, which room would you pick and what would you do?
    • If you were assigned a theme song that played whenever you walked into a room, what would it be?
    • What is a conspiracy theory you would happily believe if it turned out to be true?
    • If you had to start a cult, what would its central rule be?
    • If your life were a sitcom, what would the recurring B-plot be?
    • If you could only eat foods of one color for a year, which color and what would your diet look like?
    • What three items would make the perfect chaotic gift basket for someone like you?
    • If you had to give a fifteen-minute TED talk tomorrow with no prep, what would the title be?
    • What is the worst possible name for a child, and why do you secretly love it?
    • If you had to commit to a completely ridiculous hobby for a year, what should it be?
    • What is the dumbest hill you would die on in an argument?
    • If your life were a Wikipedia article, what would be in the "Controversies" section?
    • If you had to be reincarnated as a household appliance, which one and what brand?
    • If you could invent a holiday that only you celebrated, what would it be, when would it be, and what would the traditions be?
    • What is a completely made-up word you should start using as if everyone knows it?
    • If you could put one absurd thing in your backyard with no consequences—a moat, a Ferris wheel, an emu—what would it be?
    • If you had to swap voices with anyone for a day, whose would you pick and what is the first sentence you would say in it?
    • If aliens landed and asked you to explain humanity in one sentence, what would you say?
    • If you had a personal mascot, what would it be and what would its catchphrase be?
    • If you had to replace one of your senses with a slightly better version of a different sense, which trade would you make?
    • If you could own a single absurdly impractical vehicle, what would it be?
    • If you had to write an autobiography tonight, what would the title be?
    • If you had to share a Wikipedia page with one other person, who would it be and what would the opening sentence say?
    • If your life story were turned into a movie, who would play you and which director would ruin it?
    • If you had to be a side character in a famous novel, which one and why?
    • What is the most unhinged thing you would do if you knew there would be zero consequences for a week?
    • If you opened a museum dedicated entirely to one tiny topic, what would it be?
    • If your home had to have one ridiculous secret room, what would be inside it?
    • If you adopted a pet right now and had to give it a deeply unserious name, what would it be?
    • If you had to live inside a video game for a year, which one and what would your day look like?
    • If you had to be a ghost, what would your signature haunting bit be?
    • If you had to enter a talent show tomorrow, what would your act be?
    • If your personality were a single fictional character, who would they be?
    • If you could rename a planet, which one and what would you call it?
    • If you had to wear one outfit every day for a year, what would it be?
    • If you ran a podcast, what would the show be about and what would the worst-ever episode title be?
    • If you could mandate one petty rule that applied to everyone on earth, what would it be?
    • If your life had a tagline like a movie poster, what would it be?
    • If you had to be cursed with one mildly annoying superpower, what would it be?
    • If you could ban a single phrase from the English language forever, what would it be?
    • If you designed a personal coat of arms, what would be on it?
    • If you could host one weird themed event at your house with no judgment, what would it be?
    • If you accidentally became internet famous, what would the meme of you be?
    • If you had to start a band tonight, what would it be called and what genre would you be terrible at?
    • If you had to write a Yelp review of yourself, what would the headline say?
    • What is the worst possible name for a yacht—and the worst possible name for a tiny boat?
    • If you had to swap childhoods with one cartoon character, who?
    • If you had to live in a single decade for the rest of your life—aesthetic, music, technology, all of it—which one?
    • If you could invent one new kind of weather and add it to nature, what would it be and what would it feel like to stand outside in it?
    • If you had to enter a competitive eating contest, what food gives you the best shot at winning?
    • If you could invent a holiday and force one specific tradition on the entire country, what is the tradition?
    • If you had to choose a single emoji to describe your last week, which one?
    • If you had to switch closets with a stranger for a month, what is the first thing you would steal from theirs permanently?
    • If everyone you have ever dated got assigned a fictional villain name, what would the rules be?
    • If you had to live in a building shaped like a single object, what object?
    • If your pet (real or imagined) wrote a tell-all memoir, what would the most damaging chapter be about?
    • If you had to commit to a single ridiculous personal motto, what would it be?
    • If you had to make a single cocktail that fully represents your personality, what is in it?
    • If you had to choose a walk-up song for entering any room for the rest of your life, what would it be?
    • If you had to design a coat-of-arms-style flag for your couch, what would be on it?
    • If you had to swap lives with anyone for 24 hours and write a report afterward, who?
    • If your personality were a flavor of ice cream, what would the official scoop-shop description be?
    • If you had to invent a brand-new sport that combined two existing ones, what unholy combination would it be?
    • If you had to be reincarnated as a piece of food, what food and how would you prefer to be eaten?
    • If you lived inside a sitcom, what would the running gag about you be?
    • If you had to wear a sandwich board around town for one day with a single message, what would it say?
    • If you ran a roadside attraction, what would it be and what would the world's largest version of it look like?
    • If you adopted a houseplant and treated it like a roommate, what would its personality be?
    • If you had to write a strongly worded letter to an inanimate object, which object and what is your complaint?
    • If you could make one of your tiny habits the official law of the household, which one?
    • If you had to choose between never wearing socks again and never wearing shoes again, which?
    • If you had to get a tattoo under duress, what would be the most "you" thing to permanently mark on your body?
    • If you had to give a fake wedding toast for two strangers in five minutes, what would you say?
    • If your home had a confessional booth in the corner of every room, what would you most likely confess in each?
    • If you had to spend a month communicating only through interpretive dance, what would be the first thing you would need to convey?
    • If you got handed a key to a mystery storage unit and could only keep what fit in one bag, what would you grab first?
    • If you had to convert one room of your home into an aggressively themed space, what would the theme be?
    • If you had to design the world's worst-but-still-functioning theme park, what would the rides be?
    • If your life were turned into a movie poster for a buddy comedy, what would the tagline be?
    • If you had to design a board game based entirely on your life, what would be the win condition?
    • If your home had a "complaints department," what would the top three submitted complaints be?
    • If you had to choose one item from your home to put in a time capsule for someone to find in 200 years, what would it be?
    • If you had your own signature fragrance, what would the top, middle, and base notes be?
    • If you could trade lives with a younger version of yourself for one day, what would you do with the day?
    • If you hosted a podcast called "The Worst Possible Advice," what topic would be your specialty?
    • If you were given a billboard on a highway no one drives and you had to put something on it, what?
    • If your daily routine were a Wes Anderson film, what would the main character look like?
    • If you had to spend a year working a tiny family business, what would it be and what would your role be?
    • If you had to write a book whose title is also a complete summary of the contents, what is it?
    • If you had to live with one terrible houseguest for a month, who would it be and what would be their offense?
    • If you were a literary magazine and you had to reject the most absurd manuscript ever submitted, what would the rejection letter say?
    • If you had to design the official uniform for an imaginary profession, what would it look like and what would the profession be?
    • If you had to give every cloud you saw today a name, what is the first one you would commit to?
    • If you could replace one common sound in the world—doorbells, ringtones, sirens—with anything else, what would you swap and what would it become?
    • If your body came with a "user manual" warning label, what would the bold-print warning say?
    • If you had to give the moon a slightly more interesting job, what would you assign it to do at night?
    • If you had to host an awards show for completely useless achievements, what category would headline the night?
    • If every elevator played a song chosen by you for the rest of time, what song are you condemning humanity to?
    • If a documentary crew followed you for one day, what completely uneventful moment would they zoom in on dramatically?
    • If you had to give yourself a wrestling entrance—name, song, signature move—what would it be?
    • If you had to redesign the dollar bill and put a fictional character on it, who is getting the honor?
    • If you woke up tomorrow as the mayor of a small, weird town, what is your first executive order?
    • If you had to choose a single fruit to be the official fruit of your life, which one and why?
    • If every photo on your phone had to be replaced with one stock image, which stock image are you committing to?
    • If you had to live the rest of your life with a laugh track following you everywhere, when would it kick in most?
    • If you had to choose between a tiny dragon that sets fire to one thing per day at random or a parrot that only tells your secrets, which?
    • If you could invent a brand-new minor inconvenience that becomes a universal experience, what would it be?
    • If your phone gave you one push notification per day from your own subconscious, what would today's say?
    • If you had to invent a holiday that requires a very specific snack and a very specific grudge, what is the snack and what is the grudge?
    • If you had to give the sun a personality, what kind of guy is the sun?
    • If you had to be the spokesperson for an unglamorous product nobody thinks about, what product and what is your slogan?
    • If you could rename one constellation, which one and what is it now called?
    • If you had to design a haunted house attraction based on your most boring fear, what is inside?
    • If you had to permanently change one rule of physics for everyone, what is the new rule and what is immediately ruined?
    • If you had to write the world's worst self-help book, what is the title and what is its single piece of advice?
    • If you could replace traffic lights with anything that performed the same function, what are they now?
    • If you got to design one new emoji and force it into the keyboard, what is it?
    • If you had to commit to one fake accent for the next 24 hours, which one and where are you using it?
    • If the universe sent you a customer service survey, what is your one-star complaint?
    • If you had to teach a class titled "Things I Have Strong Opinions About For No Reason," what is the syllabus?
    • If you had to choose the soundtrack to play during the apocalypse, what is your opener?
    • If you had to give a TED Talk titled "Why ___ Is Better Than Everyone Says," what fills the blank?
    • If you could replace every public statue with a statue of a single non-historical figure, who?
    • If you woke up tomorrow fluent in a fake language, what would it sound like?
    • If you had to choose a national bird for a country that has never existed, what bird and what is the country?
    • If you had to live forever but only inside one specific building, which building?
    • If you had to invent a new fear—something humans have never been afraid of before—what is it?
    • If you had to design a cereal mascot for an aggressively boring cereal, who is the mascot and what is the cereal?
    • If you could replace the standard birthday song with anything, what is humanity now singing every year?
    • If your phone's autocorrect started replacing one word with another of your choosing forever, what is the swap?
    • If you had to host a cooking show where every recipe has to include one weird mandatory ingredient, what is the ingredient?
    • If you had to give every Tuesday a personality trait for the rest of your life, what is Tuesday like now?
    • If you had to invent a sport that can only be played in a single specific room of a house, what is the sport and which room?
    • If you could send one item back in time to confuse a historical figure, what is the item and who gets it?
    • If you had to write a love letter from a household object to another household object, who is writing to whom?
    • If you had to design a flag for a nation built entirely on one petty grievance, what is the grievance and the flag?
    • If you could give one inanimate object the ability to talk for one hour a day, what object and what would it mostly say?
    • If you had to choose a single dance move to be your only dance move forever, which?
    • If you had to invent a snack that combines two snacks that should never combine, what is it called?
    • If you had to release a perfume based on a specific season of a specific year of your life, what year, what season, what does it smell like?
    • If you could design an Olympic event that only you could win, what is the event?
    • If you had to be a contestant on a reality show built around your specific personality flaws, what is the premise?
    • If you had to live with one piece of art you find genuinely confusing hanging above your bed, what does it look like?
    • If you could replace the alphabet with 26 entirely new symbols of your choosing, what is symbol number one?
    • If you had to choose one Wikipedia article to memorize verbatim, which one?
    • If you had to give every weekday a signature smell, what does Wednesday smell like?
    • If you could insert one completely fake fact into every history textbook on earth, what is it?
    • If you had to redesign the human face by adding or removing one feature, what is the change?
    • If you had to choose a single emoji to replace your face in all photos for the rest of your life, which?
    • If you had to host a podcast interviewing only ghosts of regular, non-famous people, what is your first question?
    • If you had to commit a low-stakes crime spree, what are you stealing and where?
    • If you had to design a chain restaurant with an aggressively specific theme, what is the theme and what is on the menu?
    • If you could rename a month, which one and what is it now called?
    • If you had to live the rest of your life with one suspiciously specific superstition you just made up, what is it?
    • If you had to invent a piece of furniture that solves a problem nobody has, what is it?
    • If you could open a store that sells exactly one kind of thing, what is the thing?
    • If you had to publicly endorse one bizarre conspiracy theory for clout, which one are you picking?
    • If you had to design an amusement park ride based on your most mundane daily routine, what does it look like?
    • If you had to live in one room of a famous painting, which painting and which corner of it?
    • If you had to give a press conference apologizing for something you did not do, what would you apologize for and how convincingly?
    • If you had to take one ordinary skill and pretend it was a magical ability, what is the skill and what is the new lore?
    • If you had to choose between always smelling burnt toast or always hearing distant bagpipes, which?
    • If you had to design the menu for a restaurant called "Regrets," what is on it?
    • If you had to give every elevator ride a soundtrack based on the floor you are going to, what plays for floor 7?
    • If you had to live in a world where everyone has to wear their browser history as a name tag, what is on yours?
    • If you had to invent a new compliment that sounds nice but is actually slightly insulting, what is it?
    • If you had to choose one word to scream into the void each morning, which word?
    • If you had to design a haunted house where the scariest thing is mild social awkwardness, what is the final room?
    • If you had to write the autobiography of an animal who has never had an interesting day, what is the title?
    • If you had to commit to one weird greeting that replaces "hello" forever, what is it?
    • If you could give every restaurant in the world one mandatory new menu item, what is it?
    • If you had to design an entire holiday around one of your most annoying habits, what is the holiday and how is it celebrated?
    • If you had to choose between aging only on Tuesdays or aging in dog years on Fridays, which?
    • If you had to invent a new constellation and write its mythological backstory, what is the story?
    • If you had to choose a national anthem for a country populated entirely by chickens, what song?
    • If you had to wear a costume for the rest of your life but it could only be inspired by one minor side character from a movie, who?
    • If you had to give every traffic jam a backstory like a soap opera, what is happening in this one?
    • If you had to invent a sandwich and name it after a feeling, what is the sandwich called and what is in it?
    • If you had to choose a fictional currency for your imaginary country, what is it called and what does it look like?
    • If you had to live by one piece of advice you got from a stranger that made no sense, what is it?
    • If you had to invent a holiday for celebrating something genuinely petty, what petty thing deserves an entire day?
    • If you had to design a bumper sticker for a car driven by an emotionally complicated raccoon, what does it say?
    • If you had to choose a signature exit line for whenever you leave any room, what is it?
    • If you had to choose a single word to be aggressively whispered at you in every elevator, which word?
    • If you had to design a kids' show that secretly teaches one absurd life lesson, what is the lesson?
    • If you had to invent a new gesture that means "thank you, but also I have questions," what does it look like?
    • If you could commission a painting of yourself in any historical style, which style and what are you doing in the painting?
    • If you had to invent a fake instrument that becomes wildly popular, what does it sound like and what is it called?
    • If you had to design a board game whose only rule is "lose with dignity," how do you play?
    • If you had to give every door in your home a tiny brass nameplate describing its personality, what does the bathroom door's say?
    • If you had to choose a single famous painting to live inside as a tiny background figure, which one?
    • If you had to invent a tradition for the awkward silence after someone tells a bad joke, what is the tradition?
    • If you had to choose one absurd thing to be afraid of in public for the rest of your life, what is it?
    • If you had to design a cookbook with recipes for emotions instead of food, what is the first recipe?
    • If you had to invent a new section for the newspaper, what is in it?
    • If you had to choose a small daily ritual for an imaginary cult that you secretly think makes a lot of sense, what is the ritual?
    • If you had to design a coin and put a deeply unimportant moment from history on the back, what moment?
    • If you had to invent a phobia that becomes officially recognized, what is it the fear of?
    • If you had to write a fortune cookie message that is just mildly threatening but technically still a fortune, what does it say?
    • If you had to invent a new room for every house in the country, what is its purpose?
    • If you had to choose one childhood snack to be the official snack of your funeral, which?
    • If you had to give the wind a job title, what is it?
    • If you had to design a passport stamp for entering an imaginary country, what does the stamp say and what does the country smell like?
    • If you had to invent a new sport played entirely in slow motion, what is the objective?
    • If you had to host a talk show interviewing inanimate objects, who is your first guest?
    • If you had to design a mascot for the concept of "Sunday afternoon," what does it look like?
    • If you had to invent a holiday that absolutely cannot involve food, what is it celebrating and how is it celebrated?
    • If you had to choose one piece of furniture to be your sworn nemesis, which?
    • If you had to be the patron saint of one extremely specific small annoyance, what would you be the patron saint of?