Personal & Relational
Questions for getting to know someone, romantic relationships, family, and self-reflection.
Questions to Ask My Kids
Twenty questions to ask your own children, starting with the easy daily ones and moving toward friendships, worries, and what they wish you understood. Includes notes on when children answer best, how to adjust for age, and what to do with an answer you did not want to hear.
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Questions to Ask My Sister's Boyfriend
Twenty questions for getting to know the man your sister is seeing, with the easy ones first and the pointed ones later. Includes what not to ask, where these conversations actually work, and what to do if his answers concern you.
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Questions to Ask New Babysitter
Questions for interviewing a babysitter you have not used before, covering experience and first aid training, how they handle a child who refuses or gets hurt, phone and visitor rules, rates and cancellations, and what to check with references.
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Questions to Ask New Moms
Questions for friends and family of someone who has recently had a baby. They cover recovery and sleep, what practical help is actually missing, how the nights are being split at home, and what to ask a month or two later once the visits have stopped.
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Questions to Ask New Mothers
Questions for friends and family visiting or checking in on someone in the first weeks and months after a birth, aimed at the mother rather than the baby, covering sleep, help, recovery, visitors, and the things she may not have said out loud yet.
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Questions to Ask New Parents
Questions for friends and relatives of a couple with a new baby, whether it is their first or their third. They cover the shape of an ordinary day, how the nights are divided, which visitors help and which do not, and what to ask again once the early rush of attention has faded.
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Questions to Ask Old People
Questions for an ordinary visit with an elderly relative, neighbour or resident you do not know well, built to get past the weather and the grandchildren without turning the afternoon into an interview.
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Fun Questions to Ask Older Adults
Twenty questions for a visit with a grandparent, a neighbor or a resident at a care home. They ask about first jobs, childhood games, the food someone made best, and the advice that stuck.
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Questions to Ask Older Adults
Questions that treat an older adult as someone with a present and not only a past: what their weeks are like now, what they still do for themselves, what has got harder, and how they want to be helped when they do need it.
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Questions to Ask Older Adults About Life
Reflective questions for a long conversation with someone in later life: which years they count as the good ones, which decisions turned out to matter, what they no longer believe, and what they have never been asked.
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Questions to Ask Older Generations
Questions about how daily life actually worked in an earlier era: wages and rent, how people met, how news travelled, what was expected of you at sixteen, and what each generation got blamed for.
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Questions to Ask Older People
Questions for sitting down with an older relative to record their story while you still can: names and dates, the house they grew up in, the recipes nobody wrote down, and what they want passed on.
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Questions to Ask Older Women
Questions for getting to know a woman who is older than you, whether you met on an app, through work, or through friends. Covers her ordinary week, the life she has already built, what she wants next, and how she feels about the age gap itself.
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Questions to Ask on 2nd Date
Twenty questions for a second date, when the introductions are done and you are looking for texture: how their week actually runs, what they are like to live with, what they left out last time, what they are looking for, and where they would go next.
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Questions to Ask on 3rd Date
Questions for a third date, the point where most people decide whether to keep going. Covers how they are finding it so far, what their ordinary week looks like, how the last relationship ended, and what each of you actually wants from this.
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Questions to Ask on a 2nd Date
Questions for a second date, when the small talk is already done and you are working out whether you like the person or just liked the evening. Covers their ordinary week, their history, how they handle people, and what they made of the first date.
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Questions to Ask on a 3rd Date
Questions for a third date that go past interests and into how someone actually operates in a relationship: how they were raised, how they argue, what they do with stress, how they handle money, and what they need in order to trust someone.
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Questions to Ask on a First Date Christian
Questions for a first date between two Christians, covering church background, how faith shows up in an ordinary week, views on dating and physical boundaries, doubt, and what each of you is hoping for. Written to be asked warmly rather than as a test.
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3 Questions to Ask on a First Date: Psychology
Three first date questions worth remembering, followed by seventeen more. The note under each one says what the answer tends to tell you about how a person spends their time, how they treat the people close to them, and what they do when asked something they have not rehearsed.
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Good Questions to Ask on a Second Date
Second-date questions that move past small talk without turning dinner into an interview: how they spend unscheduled time, which arguments they handle badly, how they like to be looked after, and what they would not compromise on.
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Questions to Ask on a Second Date
Questions for the date after the first one, when the basic facts are out of the way and you are working out whether there is anything underneath the pleasantness. Deeper than small talk, lighter than the compatibility audit.
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Questions to Ask on a Third Date
Questions for the date where you decide whether to keep going: how they handle stress and conflict, what they want in the next few years, and where they think this is heading. Direct without turning the evening into an interview.
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Questions to Ask on Anniversary
Questions for a couple marking another year together: what stood out, what went unsaid, where the same argument keeps returning, and what each of you wants from the year ahead. Written for a private evening rather than a party.
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Best Questions to Ask on Bumble
Twenty questions for a Bumble chat, ordered the way a thread actually goes: an opener that gives your match something to answer, a few that get past small talk, then the ones about what they want from the app and whether they want to meet.
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Questions to Ask on Preschool Tour
Questions for a preschool tour, both while you are walking around and in the conversation with the director afterward: ratios, staffing, the shape of the day, illness and drop-off policies, and the full cost.
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Questions to Ask on Snapchat
Questions for talking to someone you have recently added on Snapchat, from openers that fit a two-line reply to ones worth saving until you have been messaging for a while.
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Questions to Ask on the Second Date
A second date is where the polite version of each person starts to wear off. These twenty questions move past first-date small talk into how someone actually lives, who they rely on, and what they are looking for, without turning the evening into an interview.
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Questions to Ask on Third Date
By a third date most people have decided they are interested and have not yet decided whether it is serious. These twenty questions suit that stage: relationship history, how someone handles conflict, what they want over the next few years, and where the two of you actually stand.
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Questions to Ask on Your Anniversary
Questions for a couple to ask each other on an anniversary, starting with easy memories and moving into what has changed this year, what each of you needs more of, and what you want the next year to look like.
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Questions to Ask on Your Anniversary
An anniversary is one of the few evenings in the year when a couple sits down with no agenda. These twenty questions cover the year just gone, the parts of it that went unsaid, and what each of you wants from the next one.
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Parenting Questions to Ask Your Partner
Twenty questions for two parents to work through together: how you split the daily load, what discipline looks like in your house, screen time, money, school, how much say the grandparents get, and what you do when the two of you disagree in front of the kids.
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Questions to Ask Parents About Parenting
Questions for asking friends, relatives, or colleagues who already have children what the job is actually like. Useful if you are expecting, thinking about it, or in the first year and looking for people who remember the details.
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Questions to Ask Parents About Their Baby
Questions for visiting new parents that go further than asking whether the baby sleeps: what she is like, the best and worst hours, feeding and sleep for the parents, who is helping and until when, and what would actually be useful this week.
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Questions to Ask Parents About Their Child
Questions for a teacher, coach, childminder, or mentor meeting a child's parents for the first time. They cover routines, health, what settles the child and what sets them off, changes at home, and how the two of you will stay in contact.
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Questions to Ask Parents Before They Die
Questions for an adult child who does not want to be guessing later. The first half covers family history and the years you were not there for. The second half covers health, documents, care, and what a parent wants at the end.
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Questions to Ask Parents on 50th Anniversary
Questions for a golden wedding anniversary, covering how they met, the wedding day, the first year, the arguments, the sacrifices, and the advice. The notes say which ones work in front of guests and which belong in a quiet room.
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