Personal & Relational
Questions for getting to know someone, romantic relationships, family, and self-reflection.
Questions to Ask Single Moms
Questions for getting to know a single mother as a friend, a new partner, or someone you have just started spending time with, without treating her situation as the only interesting thing about her. A few of these belong to close friends only, and the notes say which.
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Questions to Ask Sister
Questions for a sister you already talk to but mostly about logistics. They start with her actual week, move through comparison and birth order, and end with the practical business of how the two of you want to be in each other's lives.
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Questions to Ask Sister's Boyfriend
Questions for the first few real conversations with your sister's boyfriend: how he talks about his work, his family, and her, with notes on what to listen for and what is not worth worrying about.
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Sisterhood Round Questions to Ask PNMs
Questions for the sisterhood round of recruitment, when conversations run longer and both sides are trying to work out whether this is a fit. Written for members, with notes on what a given answer tends to tell you.
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Questions to Ask Sisters
Questions for a real conversation with a sister, from the childhood the two of you remember differently to current worries, old grievances, and how you will handle your parents getting older.
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Questions to Ask Someone About Their Culture
Questions for asking someone about their background and family without treating them as a spokesperson for a whole country, with notes on wording that goes wrong and how to follow up after the conversation.
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Questions to Ask Someone Before Marriage
Questions for couples who are engaged or close to it, covering money, children, faith, in-laws, housework, sex, and how you each behave in a fight. Each one notes what the answer tends to reveal.
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Questions to Ask Someone Before They Die
Questions for family and friends sitting with someone whose time is short. They cover life story, people, practical wishes, and things left unsaid, and they can be asked a few at a time over many visits.
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Questions to Ask Someone from a Different Culture
Questions for a friend, colleague, partner, or in-law whose cultural background differs from yours. They cover food, family, language, religious practice, and what it is like to hold two cultures at once.
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Questions to Ask Someone from Another Country
Questions for a neighbour, classmate, or new colleague who has moved here from abroad. They cover settling in, what is harder than expected, staying in touch with home, and what they would like from people here.
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Questions to Ask Someone in Recovery
Questions for a friend or family member who wants to be present for someone in recovery without prying, managing them or saying the wrong thing. The aim is to be told how to help rather than to guess, and to follow the other person's lead on language, disclosure and how much detail they want to give.
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Good Questions to Ask Someone in the Military
Questions for talking with someone currently serving, or recently out. They cover the job itself, postings and moves, training, family life, what people get wrong about the military, and plans after service. They stay away from combat, casualties and anything classified unless the person raises it.
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Questions to Ask Someone Who Cheated on You
Questions for the conversations after you find out a partner has been unfaithful. They start with the facts you need, then move to accountability, then to whether repair is possible. Written to be used slowly, over more than one sitting.
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Questions to Ask Someone Who Is High
Questions for looking after someone who is high, particularly if they seem anxious or unwell. They cover what they took, how they are doing, and what would help, in the order you would actually ask them.
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Questions to Ask Someone Who Is Retiring
Questions for a colleague, parent, or friend heading into retirement, whether you are hosting a send-off, recording something for a card, or just sitting down with them before the last day. They cover the career behind them, the practical shape of the months ahead, and the handover nobody usually gets around to asking about.
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Questions to Ask Speed Dating
Twenty questions for a speed dating night, written for the point where you have said the same three things eleven times and want a round worth remembering. Each one is quick to answer and hard to answer blandly, ordered from an easy opener to the end of the round.
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Funny Questions to Ask Spouse
Twenty playful questions to ask your spouse on a date night or a long drive, all drawn from the life you actually share: the habit that would trip a laugh track, the chore you would hand to a badly programmed robot, the argument about food, and the joke nobody outside the house has ever understood.
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Story Questions to Ask
Questions that ask for a story rather than an answer. Built for long drives, slow dinners, and the point in a conversation where small talk has run out but neither of you wants to leave.
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Questions to Ask Swingers
Questions for a couple considering the lifestyle to ask couples who have been in it for years, and for the getting-to-know-you conversation with a couple you might meet. They cover how agreements get made, saying no once you are there, testing and barriers, jealousy, and the nights that went wrong.
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Good Questions to Ask Teenagers
Questions for parents, relatives, teachers and coaches who want an actual conversation with a teenager rather than a status report. They start with what the teen is interested in and how their day went, and move toward stress, worry, and what they want from the adults around them.
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Questions to Ask Teenagers
Questions for parents, relatives, teachers, and mentors talking with a teenager, covering daily life, friendships, stress and sleep, and what they want from the adults around them.
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Good Questions to Ask Teens
Questions that get past small talk with a teenager. They begin with free time, school and what they want to learn, then move toward confidence, what success means to them, beliefs their friends do not share, fears about the future, and what they wish adults understood.
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Questions to Ask the Bride
Questions for a friend, sibling, or parent supporting a bride through wedding planning, covering where things stand, family and budget pressure, and how to offer help she will actually accept.
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Questions to Ask the Bride About the Groom
Questions to ask a bride about her groom at a shower, a rehearsal dinner, or while writing a toast, covering how they met, the proposal, and the ordinary habits she would miss.
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Questions to Ask the Elderly
Questions for talking with an older relative, neighbor, or friend about their early life, work, marriage, and what growing older has been like, with notes on pacing and on the topics that need care.
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Questions to Ask the Opposite Gender
Questions for getting to know a man or a woman you do not know well yet, whether a new friend, a coworker, or someone you are dating, written to stay away from stereotypes and to keep the exchange two sided.
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Questions to Ask to Get to Know Someone
Questions for the middle stretch of a conversation with someone new, ordered from easy openers to the ones worth saving until you have both relaxed. Written for first dates, new colleagues, and long car journeys.
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Questions to Ask to Get to Know Yourself
Twenty questions for private reflection, ordered from the ones you can answer in a sitting to the ones that take a month, ending with something small enough to act on.
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Questions to Ask Toddlers
Twenty everyday questions for a child of roughly one to three, ordered from pointing and naming through to telling someone else what happened. The aim here is talking rather than laughing: these are the questions for the walk home, the bath and the supermarket queue, and each comes with a note on why that wording gets an answer where a near-identical one gets a stare. For the silly kind, the funny questions for toddlers are the better fit.
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Questions to Ask Tour Crush
Questions for someone you have taken a liking to on a group trip, ordered from easy small talk at the back of the coach through to the two that actually decide something.
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Toxic Questions to Ask Your Boyfriend
Twenty questions that leave a partner with no answer that helps, what each one does to the conversation, and a plainer way to ask for the same thing. Written to be recognised and replaced, not used.
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Trap Questions to Ask Your Boyfriend
Playful questions that sound like tests but are safe to ask on a good evening, plus a note on the few that genuinely put a partner on the spot and how to handle those without starting a fight.
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Funny Trap Questions to Ask Your Girlfriend
Twenty playful no-win questions for a girlfriend: impossible choices, small confessions and the things she has decided not to mention. They only work as a joke, so let her dodge whichever ones she wants to dodge.
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Travel Questions to Ask
Travel questions for dinners, long car journeys and people you have just met, written so they work as well for someone who rarely leaves their county as for someone who has been everywhere.
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Travel Questions to Ask a Guy
Travel questions for early dating or a long drive with someone you are getting to know: what he does when plans fall apart, who he travels with, and what he actually enjoys once he is there.
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Trick Questions to Ask a Cheater
Questions for the conversation you have when you think a partner is lying to you, ordered from open retelling to direct, with notes on what a story that keeps moving tends to look like.
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