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APPENDIX 3: 36 QUESTIONS THAT ACCELERATE INTIMACY

This list is a variation on Arthur Aron’s 36 “Questions to Fall in Love”. The purpose of the 36 questions is to create closeness between two people by guiding them through a gradual exchange of personal stories, values, and vulnerabilities. Starting with light, easy topics and moving toward more intimate and revealing ones, the structure is designed to build trust, empathy and mutual understanding.

By sharing openly and listening attentively, both people experience a sense of being truly seen and heard, which accelerates emotional connection – sometimes even leading to feelings of love. I wouldn’t suggest this for a first date but as you progress farther along the intimacy path, this could help to accelerate your feelings of closeness.

The three sets are intentional: they mimic the natural deepening of intimacy in a relationship.

Set I – Light & Playful Curiosity – starts light and playful, so both people feel safe and comfortable.

Set II – Personal & Revealing –shifts to more personal reflections, inviting trust and honesty.

Set III – Intimate & Vulnerable – moves into vulnerability and emotional risk, where true closeness forms.

This gradual structure prevents the interaction from feeling forced or overwhelming, while still nudging both people toward deeper self-disclosure. It’s the progression through the three sets – not any single question – that makes the method powerful.

You want to set yourselves up so that you are comfortable and facing each other. One person asks the question of the other and then listens to the answer. Then the other person asks the same question and listens to the answer. You slowly work your way through all 36 questions.

Here’s how the three sets of questions mirror the natural stages of dating:

Set I → Curiosity

• Early dating feels like testing the waters: “Who are you? Do we click?”

• Light, fun questions build comfort and spark interest without pressure.

• Equivalent to a coffee date or walk date—low-stakes, easy flow.

Set II → Comfort

• Once initial curiosity is met, the next stage is building trust and connection.

• Questions dive into personal values, memories, and life perspectives.

• Equivalent to a brunch or dinner date—longer time, deeper conversation.

Set III → Commitment

• The final stage is about vulnerability and emotional intimacy.

• Questions reveal hopes, fears, and how each person relates to closeness.

• Equivalent to meeting family, sharing personal space, or first kiss—signals potential long-term intent.

AND NOW FOR THE QUESTIONS

Set I – Light & Playful Curiosity

1. If you could share a meal with anyone on earth, who would you pick?
2. Do you think being well-known is appealing? If so, for what reason?
3. When you’re about to make a call, do you plan out what you’ll say first?
4. How would you describe an ideal, perfect day in your life?
5. When was the last time you sang—either to yourself or in front of someone else?
6. Imagine you’ll live until 90: would you rather keep your 30-year-old body or your 30-year-old mind?
7. Do you have a gut feeling about how your life might end?
8. What’s something we seem to have in common already?
9. What in your life do you feel the most thankful for?
10. If you could change one thing about the way you were raised, what would it be?
11. Take four minutes and tell me your life story, in as much detail as you can.
12. If you could wake up tomorrow with one new skill or ability, what would it be?

Set II – Personal & Revealing

1. If a crystal ball could tell you the truth about yourself, your future, or anything else—what would you want to know?
2. Is there something you’ve wanted to do for a long time but haven’t? Why not?
3. What’s your proudest achievement so far?
4. What do you value most in a friendship?
5. What’s your most treasured memory?
6. What’s your most painful memory?
7. If you knew you’d die suddenly in a year, would you change the way you live today? How?
8. What does friendship mean to you?
9. What role do love and affection play in your life?
10. Share something you like about me already.
11. How close and warm is your family? Do you feel your childhood was happy?
12. How do you feel about your relationship with your mother?

Set III – Intimate & Vulnerable

1. Each of you make three “we” statements. For example: “We are both feeling…” or “We are sitting here…”
2. Complete this sentence: “I wish I had someone I could share ___ with.”
3. If we were to become close friends, what would be important for me to know about you?
4. Tell me what you like about me—be honest, things you might not say to a casual acquaintance.
5. Share an embarrassing moment from your past.
6. When was the last time you cried in front of someone? Alone?
7. Tell me something you already like about me.
8. What, if anything, is too serious to joke about?
9. If you were to die tonight with no chance to talk to anyone, what would you most regret not having said and why haven’t you said it yet?
10. Your house, with everything you own, catches fire. After saving loved ones and pets, you can safely make one last dash inside to save one thing. What would you grab?
11. Out of everyone in your family, whose death would you find most upsetting? Why?
12. Share a personal problem and ask for my advice on how I might handle it. Then, reflect back to me what you heard, to show you understood.