When two people both want to spend some time talking thoughtfully, a structured question list can help them get started. Its value is giving both people a chance to express themselves, rather than providing a script for making someone like you.
The full questions and introduction
The full article by Daniel Jones is included below, from the New York Times Chinese edition, translated here with machine assistance. See also the English questions and practice instructions. Take turns reading and answering on this page; allow about 45 minutes for the classic exercise. Our practical guidance follows the article.
The 36 questions that can quickly bring strangers closer
Daniel Jones
Illustration: Stuart Bradford
In her Modern Love essay “To Fall in Love With Anyone, Do This,” Mandy Len Catron discusses research by psychologist Arthur Aron and colleagues: intimacy between two strangers may grow quickly when they ask each other particular personal questions. The 36 questions are divided into three sets, each probing more deeply than the last.
The idea is that shared vulnerability can encourage closeness. The researchers describe a key pattern in developing a close relationship as sustained, gradually escalating, reciprocal and personal self-disclosure. Letting yourself be vulnerable with someone else can be very difficult; the exercise below pushes you to do just that.
The last thing Catron and her friend tried in her essay was to look into each other’s eyes for four minutes. That part was not documented in detail; it can last anywhere from two to four minutes. Catron nevertheless recommends it without hesitation. “Two minutes is already remarkable,” she told me. “Four minutes really works.”
Set one
- If you could choose anyone in the world, whom would you invite to dinner?
- Would you like to be famous? In what way?
- Before making a phone call, do you rehearse what you will say? Why?
- What would a “perfect” day look like for you?
- When did you last sing to yourself? And to someone else?
- If you could live to 90 while keeping either the mind or the body you had at 30, which would you choose?
- Have you ever had a secret feeling about how you will die?
- Name three things that you and your partner seem to have in common.
- What are you most grateful for in your life?
- If you could change one thing about the way you were brought up, what would it be?
- Take four minutes to tell your partner your life story in as much detail as possible.
- If you woke up tomorrow with a new talent or ability, what would you want it to be?
Set two
- If a crystal ball could tell you the truth about yourself, your life, the future or anything else, would you want to know?
- Is there something you have always dreamed of doing but have not done? Why haven’t you done it?
- What is the greatest achievement of your life?
- What do you value most in a friendship?
- What is your most precious memory?
- What is your worst memory?
- If you knew you would die suddenly within a year, would you change the way you live now? Why?
- What does friendship mean to you?
- What roles do love and affection play in your life?
- Take turns naming a good quality you see in your partner. Name five qualities each.
- Are the relationships in your family close and warm? Do you feel your childhood was happier than other people’s?
- What is your relationship with your mother like?
Set three
- Each make three true statements beginning with “we,” such as “We are both in this room feeling…”
- Complete this sentence: “I wish I had someone with whom I could share…”
- If you want to become close friends with the other person, tell them what important things they need to know about you.
- Tell the other person what you like about them. Be very honest, and say things you would not say to a casual acquaintance.
- Share embarrassing moments from your life with the other person.
- When did you last cry in front of someone else? And on your own?
- Tell the other person which qualities in them you have already come to like.
- What, if anything, is too serious to joke about?
- If you were going to die tonight with no chance to contact anyone, what would you regret not having said to someone? Why haven’t you told them yet?
- Everything you own is in your house, and the house catches fire. After rescuing your family and pets, you have time to go back safely one last time to retrieve one thing. What would you take, and why?
- Whose death in your family would upset you most? Why?
- Share a personal problem and ask the other person how they would deal with it. Also ask them to tell you honestly how they think you feel about this problem.
What the research shows
Aron and colleagues’ original 1997 study compared progressively deeper conversation tasks with small-talk tasks. The former led to greater immediate feelings of closeness. This finding does not establish that two people will fall in love or predict how long a relationship will last.
It is enough to treat the exercise as a chance to get to know each other. If you feel closer afterward, you can keep seeing each other. If you feel you are not a good fit, you have still learned something useful. Finishing the question list does not mean the other person should like you, keep dating you, or answer more questions.
Before you start, explain the invitation in one sentence
You could say: “Would you like to find somewhere quiet and take turns talking through a few questions? We can skip anything we don’t want to answer and stop whenever we like.”
Choose a time when you are unlikely to be interrupted. Use your phone only to look up the questions, rather than checking messages while answering. For a first try, there is no need to book an expensive restaurant or plan an entire day together. Choose somewhere you both feel comfortable.
Agree beforehand not to record the conversation or share screenshots of each other’s answers. When discussing someone else, leave out names and identifying details where possible. If the other person does not want to elaborate on a topic, leave it there.
Take turns answering, rather than conducting an interview
Read one question, have both people answer, then move to the next. Avoid having one person do all the talking while the other only asks questions. After hearing an answer, you can ask: “Would you like me just to listen, or would you like to hear what I think too?”
When you cannot think of an elegant answer, describing a small, specific moment can be easier than searching for the right response. For example, try starting with these questions written by this site:
- What small, everyday moment recently made you feel that someone was really listening to you?
- If we planned a weekend together without spending money, what would you want us to make time for?
- When we disagree, what would you like me to ask first, instead of rushing to explain myself?
These examples are not excerpts from the classic question list, and there is no need to score the answers. Different answers are normal. You can ask “Why does that matter to you?” without rushing to decide whose view is better.
If it feels too intense, take a step back
Later questions may touch on painful experiences, family, or relationships. You can say “Let’s skip this one” or “That’s as much as I want to say,” or return to a lighter topic. Skipping a question does not mean you are being insincere or that something is wrong with the relationship.
If either person is clearly uncomfortable, stop the exercise and ask what they need right now. Do not use a timer, a completion percentage, or “We’ve come this far” to pressure them to continue. A comfortable conversation matters more than finishing every question.
Afterward, take your time before drawing conclusions
Each of you can share one new thing you learned that day, then ask: “Would you like to find another time to keep talking?” You could arrange an ordinary walk, or leave it there. Feeling engaged that day is different from the respect, reliability, and compatibility that matter over time.
If you instead fill in answers on a website and then read each other’s responses, treat that as preparation for your next conversation. Writing can lack tone and context. When an answer is unclear, ask about it rather than labeling someone based on a single sentence. Findings from face-to-face research cannot be directly applied to asynchronous written answers.
Return to the related advice in the book
Read entry 10-05: take turns answering questions that gradually deepen. To explore the costs and choices involved in relationships further, you can also read Is marriage worth it?.
