Personal & Relational
Questions for getting to know someone, romantic relationships, family, and self-reflection.
Questions to Ask an Alienated Child
Twenty questions for a parent or relative trying to reopen contact with a child who has been turned against them. The wording is deliberately low pressure: it gives the child control over the length and depth of the conversation, and avoids asking them to judge between adults.
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Questions to Ask an Aquarius Woman
Twenty questions for getting to know an Aquarius woman, using the traits traditionally attached to the sign as prompts rather than conclusions. They run from easy openers about interests to the practical questions about time, conflict and what she will not compromise on.
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Questions to Ask an Aries Man
Twenty questions for getting to know an Aries man, treating the traits traditionally attached to the sign as prompts rather than facts. They run from easy openers about his week to the harder ground of temper, unfinished plans, rest and commitment.
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Questions to Ask an Athlete
Questions for talking with an athlete you actually know, as a friend, partner or parent: training, rest days, what the sport costs them, and how they want you to behave around results.
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Questions to Ask an Autistic Person
For friends, partners, coworkers and family who would rather ask than assume. Twenty questions about communication, sensory needs, interests and support, plus notes on how to ask so nobody feels examined.
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Questions to Ask an Elderly Person
For a visit with an older parent, grandparent, neighbour or friend: twenty questions that move past the weather and the doctor's appointment to childhood, work, friendships and the stories nobody has written down yet.
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Questions to Ask an Engaged Couple
Questions for anyone sitting down with a couple who has just got engaged: a shower host looking for a game, a friend writing a toast, an officiant preparing a ceremony, or a relative who wants to talk about the marriage rather than the seating plan.
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Questions to Ask an Introvert
Questions for a one-to-one conversation with someone who does not enjoy small talk. They start light, move toward what the person actually thinks about, and avoid the kind of prompt that puts a quiet person on the spot in front of an audience.
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Questions to Ask an Old Person
Questions for an ordinary conversation with an older neighbour, relative, or friend, weighted toward their present life and current views rather than a tour of the past.
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Questions to Ask an Old Person About Their Life
Questions for drawing out an older relative's or friend's life story, arranged from easy openers about childhood and first jobs to harder ones about hardship, regret, and what they want remembered.
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Questions to Ask an Older Woman
Questions for a younger person talking with an older woman she knows or admires, covering work, money, family, friendship, and the decisions she made against the expectations of her time.
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Questions to Ask an Older Woman
Questions for getting to know an older woman as a person rather than a source of advice: what she is doing now, what she had to fight for, what she has stopped putting up with, and what nobody ever asks her about.
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Questions to Ask an Older Woman You Like
Questions for a younger man or woman getting to know an older woman they are interested in, moving from easy conversation to the things that actually decide whether an age gap works: time, life stage, what she wants next, and whether either of you is looking for the same thing.
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Questions to Ask Anyone in Conversation
Twenty general questions for getting past small talk with almost anyone, ordered from easy openers you can use with a stranger to the ones that only work once a conversation has warmed up.
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Questions to Ask at a Baby Shower
Twenty warm, easy questions for a baby shower, written for guests who want to talk to the parents-to-be without straying into medical detail, money or unsolicited advice.
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Questions to Ask Babysitters
For the stage where you have three or four sitters to choose between and need questions that actually separate them, rather than ones any reasonable person passes. They are comparative on purpose: how many families they already juggle, which ages wear them out, how their last arrangement ended, what they would do if something better landed on a night you had booked. Once you have picked someone, a full hiring interview covers the detail of your own house.
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Baseball Questions to Ask a Guy
Twenty baseball questions for a date, a group chat or a long drive: how he ended up with his team, whether he played, the games he still brings up, his superstitions, and where he stands on how the sport has changed.
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Questions to Ask Before a Breakup
Questions to sit with before you end a relationship, working from what you are actually hoping will change, through what has and has not been said out loud, to who else this lands on and what the first month apart would look like.
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Questions to Ask Before Breaking Up With Someone
Twenty questions to work through before you end a relationship, some to answer alone and some to ask your partner out loud. Built to help you tell a hard season apart from a real dead end.
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5 Questions to Ask Before Dying
Questions for taking stock, whether you are living with a terminal illness or simply want to think this through while you are well: who you want to thank, what has never been said plainly, your wishes about care and belongings, forgiveness, and what you want to pass on. The practical ones come first, since they are the ones that can still be acted on.
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Questions to Ask Before Engagement
Twenty-one questions for two people thinking about getting engaged, working from easy ground to the harder subjects: children, money in detail, in-laws, sex, illness and what either of you would consider a dealbreaker.
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101 Questions to Ask Before Getting Engaged
Twenty questions to settle before an engagement rather than after it: whether you both want this now, what the wedding costs and who pays, actual figures for income and debt, children, whose career gives way, both sets of parents, faith at home, and what each of you would call a deal breaker.
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Questions to Ask Before Getting Engaged
Questions for couples who are seriously considering marriage, covering daily life, money, children, family, faith, and the disagreements you would rather find now than in year three.
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Questions to Ask Before Getting Engaged: A Checklist
A checklist of twenty topics to work through before an engagement, covering actual figures for income and debt, children and fertility, whose career gives way, both sets of parents, faith at home, conflict, and what each of you would call a deal breaker. Answer separately, then compare.
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101 Questions to Ask Before Getting Married
One hundred and one questions grouped by the areas that actually decide how a marriage runs: money and debt, work and time, children and fertility, the daily household, both sets of parents, faith, health, sex, how you argue, and the long view. Take one area per sitting.
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100 Questions to Ask Before Having a Baby
Twenty questions for two people deciding whether, and when, to have a baby: money, leave, nights, childcare, careers, faith, both sets of parents, and what either of you would want if it did not go to plan. Better spread across several conversations than forced into one evening.
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Questions to Ask Before Having Kids
Questions for couples deciding whether to try for a child, covering money, childcare, the division of night duty and household labour, careers, values, and what each of you is afraid of.
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300 Questions to Ask Before Marriage
Questions for a couple deciding whether to marry, kept concrete rather than abstract: money and debt, children, housework, whose career gives way, arguing, sex, in-laws, faith, illness, and what either of you would need if life went badly. Best worked through over several conversations rather than one evening.
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Questions to Ask Before Marriage
Twenty questions to work through before marrying: what each of you earns and owes, how the accounts would run, children and what you would do if they did not arrive easily, who cuts back at work when someone needs care, how you each behave in a bad argument, and what either of you thinks would end a marriage.
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Questions to Ask Before Marriage LDS
Twenty questions for a Latter-day Saint couple to work through before a sealing. They cover where each of you actually is with the church, callings and time, tithing when money is tight, children and schooling, the Word of Wisdom in social settings, doubt, in-laws, and how you handle conflict. Intended for several conversations, not one.
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Questions to Ask Before Proposing
Twenty questions to settle before you propose. The first few are practical: whether you have both actually said you want to marry, what kind of proposal and ring your partner wants, and what the timing would be. The rest are about readiness, including several you ask yourself rather than them.
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100 Questions to Ask Before You Get Engaged
One hundred questions for couples talking seriously about getting engaged, grouped by subject: what marriage means to each of you, money, children, families, home and work, conflict, sex, health, and the lines neither of you has named.
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Questions to Ask Before You Get Engaged
Twenty questions about whether the two of you are ready to be engaged, rather than a list of life admin: why now, what an engagement is for, what your recurring argument is, what each of you is giving up, and what would make either of you leave.
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100 Questions to Ask Before You Get Engaged PDF
Twenty questions to work through with your partner before an engagement, covering money, children, conflict, sex, families and health, with what to listen for in each answer.
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101 Questions to Ask Before You Get Married
One hundred and one questions arranged along the arc of a marriage: what you each think marriage is for, the legal and administrative changes nobody mentions, the first year, the first five, the middle years with children and work, money across decades, aging and dying, and how the two of you repair things.
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Book Club Questions to Ask
Twenty questions that work for almost any book club pick, arranged the way an evening tends to run: easy first impressions, then characters and craft, then themes, the ending, and where the group read the same pages differently. Written for whoever is hosting.
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