Personal & Relational
Questions for getting to know someone, romantic relationships, family, and self-reflection.
Questions to Ask a Guy to Know His Intentions
Questions for the point where you are seeing someone and do not know what it is. Written to get a direct answer about where this is going, with notes on what evasion, over-promising and honest uncertainty each look like.
20 questions
Questions to Ask a Latina
Questions for getting to know one woman properly rather than asking her to explain a whole continent. They start with the ordinary things people rarely bother to ask, and move toward family, language, what she is tired of being asked, and what she would rather you understood.
20 questions
Questions to Ask a Leo Woman
Questions for getting to know a woman whose sign is Leo, whether as a new friend or someone you are dating. The Leo description promises warmth, presence, and a taste for recognition. These questions take that as a starting point and then ask about the parts that usually go unasked: who looks after the person who organizes everyone else, and what it has cost her to be visible.
21 questions
Questions to Ask a Lesbian
Questions for a friend, sister, colleague, or daughter who is a lesbian, written for someone who wants to know her better rather than have her explain a category of people. Most are ordinary questions that tend to get skipped, a few are about how she wants things handled in front of other people, and the guide lists the ones worth leaving alone.
21 questions
Questions to Ask a Lesbian Crush
Questions for a woman you have a crush on, arranged from easy openers through to the point where you find out whether she is single, what she is looking for, and whether she wants to go out with you. Written for the situation queer women describe most often: a friendship that might be something else, and no clear way to tell.
21 questions
Questions to Ask a Long Distance Boyfriend
Questions for a boyfriend you are not in the same place as, arranged from the ordinary detail of his week through to the awkward subjects distance tends to postpone: whether the calls have started feeling like a duty, who is paying for the flights, and what has to happen for the distance to end.
22 questions
Questions to Ask a Loved One Before They Die
Questions for sitting with someone who is near the end of life: family history only they remember, practical wishes about care and belongings, and what they want said and to whom.
20 questions
Questions to Ask a Man Before Marriage
Twenty questions to work through with the man you plan to marry, covering children, money, housework, in-laws, faith and fidelity, with notes on what a vague answer usually means.
20 questions
Questions to Ask a Marine
Twenty questions for a Marine or Marine veteran you are getting to know, covering boot camp, their job and postings, life on base, what civilians get wrong, and which subjects to leave alone.
20 questions
Questions to Ask a Married Man You Are Dating
Questions for someone seeing a man who is still married, whether he calls it separated, complicated, or nothing at all. They are written to get plain answers about what is actually happening, what he expects of you, and what the next two years look like if nothing changes.
20 questions
Questions to Ask a Mature Woman
Twenty questions for getting to know a woman in her fifties or older, whether you are dating, working alongside her, or family, covering her work, her decisions, her friendships and what she wants next.
20 questions
Questions to Ask a Mother
Questions to ask your own mother about her childhood, the years before you existed, what she worried about, and the practical things worth settling early. Written for adult children who want a real conversation rather than a list of favorites.
20 questions
Questions to Ask a Mother About Motherhood
Questions for a real conversation with a mother about the early months, what she gave up, where she and her partner disagree, and the parts she has never said out loud. Written for friends, interviewers, and anyone deciding whether to have children.
20 questions
Questions to Ask a Muslim
Questions for a real conversation with a Muslim friend or colleague: prayer around a working day, Ramadan, halal food, where culture ends and religion begins, and what they are tired of explaining. Written for people who would rather ask than assume.
20 questions
Questions to Ask a Muslim Girl
Questions for getting to know a Muslim woman you are dating, courting, or becoming friends with: how she practices, where her family sits, what dating means to her, and the questions she is tired of fielding. Written to be asked out loud rather than researched behind her back.
20 questions
Questions to Ask a Narcissist Boyfriend
Questions for when a partner's behavior keeps leaving you confused, doubting your own memory, or apologizing for things you did not do. These are for gathering information rather than winning an argument or getting a confession. No list of questions can diagnose anyone, and this is not a substitute for talking to a professional yourself.
20 questions
Questions to Ask a New Coach
Questions for a consultation call with a coach you are thinking of hiring, covering training and supervision, what they actually do in a session, fees and contract terms, how they handle clients who stall, and where coaching stops and therapy begins. Written for anyone paying for coaching themselves.
20 questions
Fun Questions to Ask a New Mom
Twenty questions for a visit, a text thread or a shower after the baby arrives. They ask about the funny parts, what surprised her, the hacks she has worked out, and who is helping. Nothing that needs a hard answer on a rough day.
20 questions
Questions to Ask a New Mom
Questions for visiting or calling a friend, sister or colleague in the first months after a birth, moving from easy openers to how she is actually doing. Written for people who want to be useful rather than entertained, and includes what to avoid asking.
20 questions
Questions to Ask a New Student
Questions for teachers, peer mentors, and classmates welcoming a student who has just arrived, including mid-year transfers. They cover what the student needs today, who they have actually spoken to, where the curriculum gap sits, and what would make tomorrow easier than today. If you are a classmate rather than staff, skip the ones only a teacher can act on.
20 questions
Questions to Ask a Nigerian Man
Questions for getting to know a Nigerian man, whether you have just started dating, are about to meet his family, or simply have a friend you would rather ask than make assumptions about. Covers home region, names, language, food, family expectations, faith, money, and what he is tired of explaining.
20 questions
Questions to Ask a Parent Before They Die
Questions for the time you have left with a dying parent, covering family history, the things that have gone unsaid, and the practical wishes worth writing down. Ordered so the easier questions come first and the hardest come late.
20 questions
Questions to Ask a Penpal
Questions for letters to a penpal, whether they live an hour away or on another continent. They start with concrete, easy things to describe and move toward the questions that make a correspondence worth keeping up for years.
20 questions
Questions to Ask a Pisces Man
Questions for a longer conversation with a Pisces man, testing the traits the sign is known for against the person in front of you: creative work, intuition, moods, boundaries, and what he needs from a partner.
20 questions
Questions to Ask a Poly Couple
These twenty-one questions are for the point where you are getting to know a couple who are polyamorous: you are seeing one of them, considering seeing both, or you are a friend who would rather ask than guess. They cover the agreements you would be living inside, whether either partner can end your relationship without being in it, where you would fit in an ordinary week, and what went wrong the last time. Direct rather than intrusive, and phrased so nobody has to defend polyamory to you before they answer.
21 questions
Questions to Ask a Postpartum Mom
For friends, siblings, partners, and parents visiting someone in the first months after birth. These are questions about her rather than the baby, ordered so the easy ones come first and the harder ones only if she wants them.
20 questions
Questions to Ask a Potential College Roommate
The short list of questions people avoid in July and wish they had asked by October. They are about partners staying over, money owed between you, drinking and smoking in the room, what a previous roommate would say about them, and the things each of you genuinely cannot live with. If you want the whole conversation rather than the difficult end of it, the full pre move-in set is longer and gentler.
20 questions
Questions to Ask a Potential Husband
Twenty questions for the stretch between dating seriously and getting engaged: money and debt, children and daily care, whose work moves first, conflict, faith, and what he has already decided he will not bend on. Meant to be spread over weeks, not asked in one sitting.
20 questions
Questions to Ask a Potential Roommate (College)
The practical conversation, for the weeks between being matched and arriving. It covers who is bringing the fridge, the microwave and the rug, what is worth splitting the cost of, arrival times on move-in day, storage, and how the room will be laid out. Nothing here is about habits or house rules, which are worth a separate and longer conversation before term starts.
20 questions
Questions to Ask a Potential Spouse
Twenty questions for two people deciding whether to marry each other: where you live, how money is held, children and whose work gives way, care of ageing parents, names, wills and illness, and what each of you would find hard to forgive. Written to be worked through over months.
20 questions
Questions to Ask a Potential Sugar Daddy
Questions for the stage before you agree to anything: what he actually wants, what he expects in return, how money would move, and the specific requests that mark a scam rather than an arrangement. Written for the messaging stage, before a first meeting, and from the point of view of the person with less power in it.
20 questions
Questions to Ask a Potential Wife
Twenty questions for the months before a proposal: what she does not want to give up, her work and how children would change it, what she would need during a pregnancy, money kept separate and money shared, in-laws, and what she has been reluctant to ask you for.
20 questions
Questions to Ask a Reader
Questions for talking with someone who reads, at a book club, on a first date, or with a friend whose shelves you keep eyeing. They start with what is on the nightstand now and move to rereads, abandoned books, and the ones that changed their mind.
20 questions
Questions to Ask a Senior
Questions for a long conversation with an older relative, neighbour or friend, arranged from easy recollection towards the things people rarely get asked. Includes guidance on recording, pacing and what to do when memory is uneven.
20 questions
Questions to Ask a Single Mom
Questions for a friend, relative or new partner who wants to know a single mother better and be genuinely useful, covering how her week actually runs, what help lands and what does not, and the assumptions she is tired of correcting.
20 questions
Questions to Ask a Sister
Questions for a sister you already know well but may not know currently: what she remembers differently from you, what she carries from your family, and what she wants from the relationship now that you are both adults.
20 questions