Personal & Relational
Questions for getting to know someone, romantic relationships, family, and self-reflection.
Tricky Questions to Ask Your Boyfriend
Twenty questions that are hard to answer with a shrug, arranged so the ones about daily life come first and the ones about trust, money and the future come once you are both already talking.
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Questions to Ask Twins
Questions to ask a twin about school, mistaken identity, competing with a sibling the same age, and what changed once the two of them started living apart.
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Uncomfortable Questions to Ask Your Daughter
Twenty direct questions for a parent who wants the honest version rather than the polite one, covering how she reads you, what she is not saying, and the situations she may need help getting out of.
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Unhinged Questions to Ask Your Boyfriend
Twenty absurd questions with enough of a premise to actually answer, ordered so the short silly ones come first and the ones that need a full committed bit come once he is warmed up.
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Questions to Ask Ur Dad
Questions for a real conversation with your dad, from his first job and what he was like at your age to what he would do differently as a parent and what he has never got around to saying.
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Questions to Ask Ur Sister
Questions for a proper conversation with your sister, covering what she remembers from childhood that you do not, how your parents treated each of you, what she has never said out loud, and what you both want the relationship to be.
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Valentine's Day Questions to Ask
Twenty Valentine's Day questions for couples at any stage, from easy openers over dinner to the searching ones about what you each want next. Pick a handful instead of working through the whole list.
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Questions to Ask Venue for Wedding
The money conversation, for once a venue is on your shortlist and you need to know what the day will actually cost. It covers the minimum spend and how it is measured, service charge and tax, what is billed per head, corkage and cutting fees, which prices can still rise, and what couples end up paying for that they did not expect. For the terms themselves, the contract questions are a separate conversation.
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Very Funny Flirty Questions to Ask a Girl
Twenty light, funny questions for texting or a first date, ordered from silly openers to the ones that only work once she is already laughing. Each comes with a note on what the answer tells you and where in the conversation it belongs.
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Questions to Ask Wedding Guests
Twenty questions for talking to people at a wedding, whether you are the couple working the room or a guest seated next to strangers: easy openers, questions that produce stories about the couple, and a few slower ones for later in the evening.
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Questions to Ask Wedding Guests on RSVP
Twenty questions worth putting on a wedding reply card or online RSVP form, covering attendance, names, meal choices, allergies, access needs, travel and seating, with notes on how to word each one so guests answer it.
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What Are Good Questions to Ask at a Book Club
Twenty questions for a book club discussion, starting with the ones anybody can answer and moving to the ones that split the room. Each comes with a note on what it tends to surface and how to follow up. Works for fiction and non-fiction, and for groups where not everyone finished the book.
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What Are Good Questions to Ask Your Crush
Twenty low-pressure questions for someone you like but do not know well yet, ordered from easy to more personal. Each has a note on what the answer tends to tell you, including how to read whether the interest runs both ways. Works over text or in person, and the guide covers when to stop asking and say something instead.
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What Are Some Good Questions to Ask Elderly
Twenty questions for visiting an older parent, grandparent, neighbor or resident, starting with their life as it is now and moving into the past. The notes explain what each question tends to open up, and the guide covers hearing loss, memory changes and recording a story before it is lost.
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What If Questions to Ask Your Boyfriend
Twenty what if questions for your boyfriend, starting light and ending with the hypotheticals that are really about money, moving, family and the next ten years. Each has a note on what the answer usually reveals and where a hypothetical is doing the work of a conversation you have been avoiding.
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Questions to Ask When Courting
Questions for two people who are dating with marriage in view: what an ordinary week looks like, money and debt, how each family expects to be involved, children, how each of you argues and recovers, physical boundaries during courtship, and the history worth telling each other early. Ordered so the lighter ones come first.
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Questions to Ask When Dating Someone With a Child
Questions for dating a parent, covering the parts that are easy to leave unsaid: how the custody schedule really works, what the relationship with the other parent is like, when and how you would meet the child, house rules, money, holidays, and what role you would be expected to take. Written for the partner who is not the parent.
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Questions to Ask When High
Questions for a slow evening with friends: sensory ones to open with, funny and curious ones in the middle, a few that go somewhere quieter later. Includes notes on reading the room, keeping things comfortable for anyone feeling anxious, and which questions to leave alone.
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Questions to Ask Yes or No
Twenty questions that can honestly be answered with one word, for car rides, waiting rooms, first dates and anyone who goes quiet when asked something open. Each one comes with what the answer tends to tell you and the follow-up worth asking once it lands.
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Good Yes or No Questions to Ask a Girl
Twenty short yes-or-no and either-or questions for early conversation: coffee or tea, window or aisle, dancing at weddings, hosting or being invited, whether she plans trips or just shows up. Each one comes with a note on the follow-up, so a one-word answer does not end the exchange.
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Questions to Ask Your 3 Year Old
Short questions a three year old can actually answer, for the car, the walk home from daycare, the bath and the ten minutes before sleep. Three year olds do better with who, what and where than with why, and better with two choices than with an open question, so these are built that way.
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Questions to Ask Your 8 Year Old
Questions for an eight year old who answers fine to everything. At this age children track fairness closely, notice who is left out, and start deciding which worries to keep to themselves, so these are aimed at the lunch table, the classroom rules and the things they have stopped mentioning.
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Questions to Ask Your Aunt
Questions for a proper conversation with your aunt, who watched your parent grow up and remembers the household from the inside: what your mother or father was like young, the parts of the family story that got quietly edited, relatives you never met, health history worth writing down, and what she remembers about you as a small child.
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Questions to Ask Your Baby Daddy
Questions for a co-parent you are no longer with: parenting time tied to his actual work schedule, money as an amount and a date, house rules across two homes, who else is in the home, medical and school decisions, and how you both keep a child out of the middle when the two of you disagree.
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Questions to Ask Your Best Friend's Boyfriend
Questions for getting to know the person your closest friend is with, asked over dinner or a long drive rather than across a table like an interview: how he talks about her, who else he leans on, what the two of them argue about, and how he is finding a friendship group he inherited fully formed.
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Questions to Ask Your BF About His Ex
Questions for asking a boyfriend about his ex, starting with the plain facts and moving toward the harder ones. Each note says what different answers tend to reveal, including which details are usually better left unasked.
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Questions to Ask Your Biological Father for the First Time
Questions for a first meeting with a biological father, whether contact came through a DNA test, a registry, an adoption record or a relative. They cover practical ground such as what to call him, family medical history and half-siblings, the history of what happened, and a plain conversation about how much contact each of you wants.
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Questions to Ask Your Boyfriend About His Career
Questions for talking with your boyfriend about work: what his days actually consist of, the people around him, the parts he would drop tomorrow, how he feels about what he earns, whether he would move for a job, and what he needs from you when work is going badly.
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Questions to Ask Your Boyfriend About His Dreams
Questions for a long conversation with your boyfriend about what he actually wants: the ambitions he dropped and why, where he pictures living, whether he wants children, who he envies, what he is afraid to say out loud, and the smallest step he could take toward any of it.
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Questions to Ask Your Boyfriend About His Ex
Twenty questions for the conversation about your boyfriend's ex: how the relationship ended, how much contact is left, and what he took from it. Written for someone who wants the facts and the feel of it rather than reassurance, with notes on what a settled answer tends to sound like.
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Questions to Ask Your Boyfriend About His Family
Twenty questions about your boyfriend's family, from who he actually talks to and how holidays work to what he plans to do differently than his parents did. Useful before you meet them, and useful again once the relationship starts making claims on both families.
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Questions to Ask Your Boyfriend About His Fears
Twenty questions that get at what your boyfriend actually worries about, starting with the low-stakes ones and working toward money, health, ageing and the relationship itself. Includes what to do when he tells you something you cannot fix.
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Questions to Ask Your Boyfriend About His Friends
Twenty questions about the people around your boyfriend: who he would call first, who he only texts, and how much of his week belongs to them. Useful before you meet the group, and useful again when his social life and yours start having to share a calendar.
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Questions to Ask Your Boyfriend About His Future
Twenty questions about the practical shape of your boyfriend's future: where he expects to live, whether he wants children and by when, what his work is heading toward, and which decisions are coming whether he plans for them or not. Written for the point where you need to know whether two futures fit.
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Questions to Ask Your Boyfriend About His Goals
Twenty questions about what your boyfriend is actually working toward and how he goes about it: what he has finished, what he keeps restarting, what he abandoned, and what he would need from you to get somewhere. Less about ambition in the abstract than about follow-through.
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Questions to Ask Your Boyfriend About His Hobbies
Twenty questions about what your boyfriend does with his own time: what he has kept up for years, what it costs in hours and money, what he gave up, and whether he wants company or wants it left alone. Includes what to do the first time he takes you along.
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