Personal & Relational
Questions for getting to know someone, romantic relationships, family, and self-reflection.
Questions to Ask Your Little Sister
Questions for an older sibling who wants more than small talk with a younger sister, moving from her week and her friends to school, worries, and what she wishes you understood. Includes notes on adapting them for a child, a tween, and a teenager.
20 questions
Questions to Ask Your Long Distance Boyfriend
Questions for a relationship conducted mostly by phone, covering the ordinary detail you are missing, how often you each actually want to talk, jealousy and going quiet, visits and the days after them, and when the distance ends. Ordered from easy to the ones worth scheduling.
20 questions
Questions to Ask Your Long Distance Girlfriend
Questions for calls and texts with a girlfriend you cannot see in person: easy daily catch-ups, honest talk about what the distance costs, and the practical question of how it ends.
20 questions
Questions to Ask Your Long-Distance Partner
Questions for a relationship conducted over calls and visits: the daily rhythm, what the arrangement costs each of you, and the conditions that would end it.
20 questions
7 Questions to Ask Your Mom
Seven questions short enough to hold in your head, written for an ordinary phone call rather than a planned sit-down. The first seven are the ones to remember; the thirteen after them are there for the calls that keep going. If what you actually want is her life history written down, with names, dates and the family record, the ten-question set is built for that instead.
20 questions
10 Questions to Ask Your Mom
A set for the conversation you have with a notebook open: the names, places and dates that only your mother still holds, plus the recipes, photographs and objects that lose their story the moment nobody can explain them. If you want a shorter set to keep in your head for an ordinary phone call, the seven-question version is built for that.
20 questions
Questions to Ask Your Mom About Her Life
Questions for a long conversation with your mother about her own life: her childhood, her first jobs, her marriage, and the family history only she can tell you.
20 questions
Questions to Ask Your Mom Before She Dies
Questions for the conversations you want to have with your mother while there is still time: her life and memories, what she wants medically and afterward, and what she wants you to know.
20 questions
Questions to Ask Your Mom's Boyfriend
Questions for getting to know the man your mother is seeing: easy ground for a first meeting, and the more direct ones worth asking once you have met him a few times.
20 questions
Questions to Ask Your Mother About Yourself
Questions to ask your mother about your own early years: what you were like before you can remember, what she kept from you at the time, and how she sees you now.
20 questions
Questions to Ask Your Mother Before She Dies
Questions for a mother's last months: her memories and family history, the practical arrangements, and the things that are much harder to ask about later.
20 questions
Questions to Ask Your New Friends
Questions for someone you have only recently started spending time with: easy ground for a first coffee, and the ones worth saving until it is clear the friendship is going somewhere.
20 questions
Questions to Ask Your OC
Twenty questions to put to your own character in their own voice, for writers and roleplayers whose pages of backstory notes have not yet made the character feel like a person.
20 questions
Questions to Ask Your Older Sister
Questions for a one-to-one conversation with an older sister, moving from shared childhood memory to the things birth order kept from you: what she carried, what she was told, and what she wants from you now.
20 questions
Good Questions to Ask Your Parents
Twenty questions to ask your parents about the house they grew up in, how they met, the first year of parenting, the tightest stretch financially, which traditions they actually care about, what they worry about now, and how they want to be looked after later on.
20 questions
Questions to Ask Your Parents About Their Childhood
Questions about the years before you existed: the house, the street, the money, the people your parents answered to. Written for an adult child who wants the details recorded while they still can be, with advice on how to ask.
20 questions
Questions to Ask Your Parents About Their Life
Questions for a recorded or written conversation with a parent about their childhood, work, marriage, choices and regrets, for adult children who want the story in the parent's own words while they can still tell it.
20 questions
Questions to Ask Your Parents Before They Die
Questions for adult children who want both halves of the conversation with an ageing parent: the memories and family history that only they hold, and the practical wishes, documents and instructions that are hard to ask about later.
20 questions
Questions to Ask Your Parents Before They Die Book
Twenty questions sized for a keepsake book, one to a page, for families making a written record of a parent's life in their own handwriting or dictated word for word.
20 questions
Questions to Ask Your Parents Before They Die Printable
Twenty short questions written to be printed and read aloud, one line each, for families sitting down with an ageing parent to write or record their answers over several visits.
20 questions
1000 Questions to Ask Your Partner
A very long list for couples who have run out of new things to ask, arranged in sections so you can pick one to suit the evening: how you met, childhood and family, friendship, work and money, the household, food and travel, health, sex, conflict and trust, fear, grief and regret, belief, taste and humour, ambition, children, aging and dying, and the two of you.
990 questions
Questions to Ask Your Partner About Parenting
Questions for two people working out how they will actually parent together: discipline, screens, school, religion, grandparents, and what happens when one of you thinks the other handled it badly. Useful before children arrive or in the middle of it.
20 questions
Questions to Ask Your Partner About Their Past
Questions about the years before you, ordered so the light ones come first: early jobs, old friendships, abandoned plans, then past relationships and the things they have not told you yet. Includes advice on how to ask without it becoming an interrogation.
20 questions
Questions to Ask Your Partner Before Marriage
Questions for engaged couples to work through before the wedding, covering money and debt, children, conflict, family boundaries, faith, care of ageing parents, and what each of you would need in order to ask for help.
20 questions
Questions to Ask Your Partner Before Moving In
Questions for couples about to share an address, covering the lease and the deposit, who pays what, cleaning standards, guests, sleep, space, and what happens if living together does not work.
20 questions
Questions to Ask Your Pen Pal
Questions built for letters rather than conversation, for a new or long-standing pen pal, moving from concrete details about their day and their street to the things people write more easily than they say.
20 questions
Questions to Ask Your Poly Partner
Questions for a check-in with a partner in an open or polyamorous relationship, covering time, disclosure, jealousy, sexual health agreements, introductions, and the practical entanglements nobody wrote down. Written for a real conversation between two people, not a negotiation with a template.
20 questions
Questions to Ask Your Role Model
For a coffee, a mentoring call or a chance conversation with someone whose work you admire. Twenty questions that get past the tidy version of their story to the trade offs, the luck, the things they quit and what they would tell you to ignore.
20 questions
Funny Questions to Ask Your Siblings
Almost all sibling humour lives in childhood. These twenty stay in the present, on the people you have both actually turned into: the search history, the useless skills, the elaborate lengths one of you goes to in order to avoid a five-minute job, and the parent phrases you can now hear yourselves saying. Nobody has to remember 1998. For the childhood material, the funny questions to ask siblings set covers the old house.
20 questions
Questions to Ask Your Siblings
For siblings who see each other a few times a year and mostly end up talking about the past. These twenty stay in the present tense: what each of you is working on, who is around you now, what has changed since you last spoke properly, and what the other has been assuming about your life that stopped being true years ago. If you would rather compare childhoods, the questions to ask siblings set starts there.
20 questions
Questions to Ask Your Siblings About Yourself
For anyone who wants an honest read on themselves from the people who saw the early version. Twenty questions to ask a brother or sister about your patterns, your blind spots and the parts of you that have and have not changed.
20 questions
Questions to Ask Your Significant Other Before Marriage
Twenty direct questions to work through before a wedding: money and debt, children and timing, in-laws and holidays, housework, conflict, faith, sex, and what each of you would call a dealbreaker. Written for couples who are already committed and want the specifics said out loud.
20 questions
Fun Questions to Ask Your Sister
Twenty questions for a sister you see every week or once a year. They cover shared childhood, the habits she has clocked and never mentioned, what she thinks of your life now, and the trip the two of you keep putting off.
20 questions
Questions to Ask Your Sister
Twenty questions for a real conversation with a sister, moving from childhood memories to harder ground: whether your parents were fair, what each of you took from watching the family, and what she needs from you that she has never asked for.
20 questions
Questions to Ask Your Sister About Yourself
Twenty questions to ask a sister about you: what you were like as a child, the habits you cannot hear yourself repeat, the role you were handed in the family, and the things she has noticed for years and never said. For anyone who wants the outside view from the person who has watched longest.
20 questions
Questions to Ask Your Sister in Law
Questions for the woman who married your brother, or for your spouse's sister, once the polite phase has gone on long enough. They cover how she found your family, what she would change about family occasions, and the practical things in-laws usually route through a third person rather than ask directly.
20 questions