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Question 1

What helps you feel safe again after a rupture?

Question 2

When you say you’re fine, what does it actually mean?

Question 3

When you get hurt, how do you protect yourself?

Question 4

What is the most traumatic experience you’ve had in your life and how does the residue of that experience show up in your present?

Question 5

What are the words you’ve always wanted to hear somebody say?

Question 6

What would have to be true for you to tell me it’s been the best three years of my life?

Question 7

Do we carry every experience we have had in our bodies?

Question 8

What can you teach me?

Question 9

Parts of yourself you are afraid to look at?

Question 10

A time in your life when all of the stars aligned and you felt like you were exactly where you were meant to be…

Question 11

What don’t you do? Sharing struggles. What is sacrificed so that you can unload your burden of responsibility?

Question 12

What did it take you too long to learn about yourself?

Question 13

If you were the main character on a movie of your life, what would the audience be screaming at you to do right now?

Question 14

What is the last thing you changed your mind about?

Question 15

What’s one book you think everyone should read?

Question 16

How do you keep busy during the day?

Question 17

If you could have done a job aside from the current one, which one would it be?

Question 18

Which is the best family trip you remember from childhood?

Question 19

What is your hidden talent?

Question 20

What are your top three bucket list items?

Question 21

What experience has changed your perspective on life?

Question 22

What’s the biggest risk or adventure you’ve taken lately?

Question 23

Favourite way to spend a weekend?

Question 24

What’s something you’ve always wanted to try but haven’t had the chance to yet?

Question 25

Most valuable lesson you’ve learned from past relationships?

Question 26

Who are important women/men in your life?

Question 27

What aspects of your personality and you scared that other people will see?

Question 28

Tell me something about your day.

Question 29

What’s been the highlight of your day?

Question 30

Do you have anything exciting coming up?

Question 31

What’s a passion project you’re working on right now?

Question 32

What’s the pain on me you’d like to heal and why?

Question 33

If you were in a room with everyone you’d ever met, who would be the one you’d look for?

Question 34

If someone gave you a box of everything you had ever lost, what is the first thing you would look for?

Question 35

If you had the chance to relive one day of your life, what day would it be and why?

Question 36

Imagine you had a chance to revisit a moment from your past, which moment would you choose? And what would you do differently? If anything.

Question 37

The person who taught you the most about love?

Question 38

The parts of your parents you are most afraid of becoming?

Question 39

What do you feel inspired to explore more deeply at this point in your life?

Question 40

If you could relive any moment in your life, what would it be?

Question 41

Where in your life do you need to stop asking ‘what if it goes wrong?’ and start asking ‘how good could it get?’

Question 42

What type of music do you like, and what’s the last concert you went to?

Question 43

When you travel, do you like to have a packed itinerary for max efficiency or do you prefer a chill vibe with flexible plans?

Question 44

What’s one thing you’re looking forward to doing this year?

Question 45

What are your top three favorite TV shows of all time?

Question 46

What does a typical weekend look like for you?

Question 47

What qualities do you value in a romantic relationship?

Question 48

How important is _____ to you?

Question 49

What’s your preference on paying at the end of a date?

Question 50

If you had the power to address any cause or social issue, which one would you choose?

Question 51

What role do your family and friends play in your life? Do you have a close relationship with them?

Question 52

Who would you consider your support system?

Question 53

What’s your approach to finding work-life balance? Is that important to you?

Question 54

Have you ever been in a serious relationship?

Question 55

What’s the longest relationship you’ve been in?

Question 56

Why did your last relationship end?

Question 57

What’s your perspective on exes remaining friends after a breakup? Are you friends with any of your exes?

Question 58

What’s something you’ve learned about yourself during your single years or from your last relationship?

Question 59

What are you looking for based on the relationships that you’ve been in or your time being single?

Question 60

What’s something that often triggered you in your previous relationships?

Question 61

What do all your exes have in common? What do you think attracts you to them?

Question 62

How do I find you today?

Question 63

What is the fullest version of this friendship?

Question 64

If we met a treat from now what would we be celebrating?

Question 65

If the last five years was a chapter in your life, what would the chapter be about?

Question 66

What would you do if you weren’t afraid?

Question 67

What talent do you have that you’re not using?

Question 68

You only get one song to listen to for the rest of your life. What is it?

Question 69

How will we fix it when things go wrong?