By Danielle Andrews
What kind of questions do you usually ask someone you’ve just met? Getting to know someone new can feel like a delicate dance. You start with the basics—work, hobbies, where they grew up—but soon, the conversation can stall. How do you move beyond surface-level chatter and build a genuine connection? The answer often lies in asking the right questions.
Thoughtful questions open doors to deeper understanding and intimacy. They invite vulnerability and show a sincere interest in who a person truly is, beyond their daily routine. This isn’t just about finding common ground; it’s about exploring the unique experiences, values, and dreams that shape an individual. As author and speaker Brené Brown says, “Connection is the energy that exists between people when they feel seen, heard, and valued; when they can give and receive without judgment; and when they derive sustenance and strength from the relationship.”
In 1997, psychologist Arthur Aron published a groundbreaking study called “The Experimental Generation of Interpersonal Closeness.” Participants were paired with a stranger, and for 45 minutes, they asked each other a series of 36 specific questions. These questions were designed to escalate in personal intensity, fostering a sense of closeness and intimacy.
The study gained widespread attention in 2015 when writer Mandy Len Catron wrote about her experience with the questions in a Modern Love essay, “To Fall in Love With Anyone, Do This.” Catron explored whether it was possible to accelerate intimacy and even fall in love with someone by working through Aron’s list. “Most of us think about love as something that happens to us. We fall. We get crushed,” she wrote. “But what I like about this study is how it assumes that love is an action.”
Aron’s study is a powerful reminder that building intimacy is an active process. While the questions became famous for their romantic potential, their true value lies in their ability to foster connection with anyone important in your life—a new friend, a family member, or a long-term partner.
How to Use These Questions
The key to making these questions work is creating a safe and open environment. This isn’t an interrogation; it’s a shared exploration. Not necessarily intended to be done all in one setting, but a good list to chomp on … or nibble on.
- Be genuinely curious: Ask because you truly want to know the answer, not just to fill the silence.
- Listen actively: Pay attention to what the other person is saying without planning your response. Ask follow-up questions to show you’re engaged.
- Share your own answers: Vulnerability is a two-way street. Be willing to open up and answer the questions yourself. This builds trust and mutual respect.
- Don’t rush: Take your time with each question. Let the conversation breathe and follow natural tangents. The goal is connection, not completing a checklist. And by no means does this need to happen in one sitting.
The 36 Questions for Deeper Connection
Dr. Aron’s questions are divided into three sets, each more probing than the last. This gradual progression helps build a foundation of trust before moving into more personal territory.
Set I: The Warm-Up
This first set of questions starts a bit lighter, breaking the ice and getting the conversation flowing. They are designed to be easy to answer while still revealing interesting aspects of a person’s personality and preferences.
- Given the choice of anyone in the world, whom would you want as a dinner guest?
- Would you like to be famous? In what way?
- Before making a telephone call, do you ever rehearse what you are going to say? Why?
- What would constitute a “perfect” day for you?
- When did you last sing to yourself? To someone else?
- If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?
- Do you have a secret hunch about how you will die?
- Name three things you and your partner appear to have in common.
- For what in your life do you feel most grateful?
- If you could change anything about the way you were raised, what would it be?
- Take four minutes and tell your partner your life story in as much detail as possible.
- If you could wake up tomorrow having gained any one quality or ability, what would it be?
Set II: Digging a Little Deeper
The second set of questions encourages more reflection and touches on more significant life experiences and values. This is where you begin to learn about what truly matters to someone.
- If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?
- Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
- What is the greatest accomplishment of your life?
- What do you value most in a friendship?
- What is your most treasured memory?
- What is your most terrible memory?
- If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
- What does friendship mean to you?
- What roles do love and affection play in your life?
- Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items.
- How close and warm is your family? Do you feel your childhood was happier than most other people’s?
- How do you feel about your relationship with your mother?
Set III: Getting to the Core
The final set of questions is the most personal. It asks for vulnerability and honesty, inviting participants to share their feelings, fears, and inner worlds. By this point, a level of trust should be established, making these deeper questions feel more natural.
- Make three true “we” statements each. For instance, “We are both in this room feeling …”
- Complete this sentence: “I wish I had someone with whom I could share …”
- If you were going to become a close friend with your partner, please share what would be important for him or her to know.
- Tell your partner what you like about them; be very honest this time, saying things that you might not say to someone you’ve just met.
- Share with your partner an embarrassing moment in your life.
- When did you last cry in front of another person? By yourself?
- Tell your partner something that you like about them already.
- What, if anything, is too serious to be joked about?
- If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?
- Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?
- Of all the people in your family, whose death would you find most disturbing? Why?
- Share a personal problem and ask your partner’s advice on how he or she might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.
Cultivate Meaningful Connections
Meaningful relationships don’t just happen; they are built through intentional effort and a willingness to be open. These 36 questions provide a powerful framework for that process. They remind us that everyone has a rich inner world waiting to be discovered.
Whether you use this list with a new date, a friend you want to know better, or even a family member, the act of asking and listening can transform your relationships. It’s an invitation to move past the superficial and connect on a level that truly matters. Take the time to ask, to listen, and to share. You might be surprised by the depth of connection you can build.
If you’re still looking for that special person to share your life with, give us a call and allow our talented matchmakers to get to work on your behalf!
