Deep Discussion Questions

Question 1

What emotion do you think you experience more intensely than other people do?

Some sample emotions to get you thinking: anxious, angry, frustrated, joyful, sad, awestruck, scared, worried, annoyed, laughing, bravery, contentment, confident, startled, craving, love, gratitude, finding things cute, jealousy, embarrassment, etc.

Answer 1

(Either answer the question yourself, and/or go around the circle and give others the option to reply. It’s ok to pass.)

Question 2

What’s the most intense emotional pain you’ve ever experienced?

Answer 2

(Either answer the question yourself, and/or go around the circle and give others the option to reply. It’s ok to pass.)

Question 3

Is there anything about this [event/night] that made you nervous beforehand?

Answer 3

(Either answer the question yourself, and/or go around the circle and give others the option to reply. It’s ok to pass.)

Question 4

What is an offensive comment made about you before that you simply cannot forget or let go?

Answer 4

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Question 5

Have your parents done a good job?

Answer 5

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Question 6

How have you disappointed your parents?

Answer 6

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Question 7

Which of your achievements are you most proud of?

Answer 7

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Question 8

Do you have any life regrets? What would you change?

Alternate or Addendum: If you went back to that age to give yourself that advice, do you think you would have accepted it?

Answer 8

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Question 9

What’s the most intense physical pain you’ve ever experienced?

Answer 9

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Question 10

How can you tell if someone REALLY knows and understands you?

Answer 10

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Question 11

What are your coping mechanisms for stress?

Answer 11

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Question 12

Which of your personality traits are you most proud of?

Answer 12

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Question 13

What have you done that you are most ashamed of?

Answer 13

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Question 14

If you could ask the universe one question and get the truth, what would you want to know?

Answer 14

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Question 15

Would you prefer to date someone 20 IQ points higher or 5 points lower than you?

Answer 15

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Question 16

If you had to pick two people from this group to be your parents, who would you pick and why? (doesn’t need to be a couple or even the same sex)

Answer 16

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Question 17

What about your appearance would you like to change?

Answer 17

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Question 18

What is the most significant thing you’ve ever changed your mind about?

Answer 18

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Question 19

What about your personality would you like to change?

Answer 19

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Question 20

What was the last thing you cried about? When was it?

Answer 20

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Question 21

What was your biggest financial mistake?

Answer 21

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Question 22

What are you waiting to hear from someone close to you?

Answer 22

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Question 23

What emotion/feeling are you currently suppressing or ignoring?

Answer 23

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Question 24

In what ways do you tend to fail at communication?

Answer 24

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Question 25

What do you still owe someone an apology for?

Why haven’t you done it yet?

Answer 25

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Question 26

What is currently your greatest insecurity?

Answer 26

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Question 27

What do you think enlightenment is?

Answer 27

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Question 28

Apologize to someone in the group for something you’ve done to them

Answer 28

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Question 29

Would you rather double the amount of emotional pain and pleasure you feel on a daily basis, or cut both in half?

Answer 29

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Question 30

Have you ever had (what you consider to be) a spiritual experience? If so, what was it like and what effects did it have on you?

Answer 30

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Question 31

Would you rather be blind or deaf? (You must choose one)

Answer 31

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Question 32

What about yourself have you been trying to fix for a long time?

Answer 32

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Question 33

In what ways don’t you trust yourself?

Answer 33

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Question 34

What relatively common experience have you never had?

Answer 34

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Question 35

What difficult or painful experience would you actually recommend to everyone?

Answer 35

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Question 36

What is the best advice you’ve received, and why did you need it?

Answer 36

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Question 37

What’s the most sick (mental or physical) you’ve ever been?

Answer 37

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Question 38

What is something that would make you a better person, but you just don’t want to do it?

Answer 38

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Question 39

Which of your habits conflicts with your values?

Answer 39

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Question 40

What was the most difficult thing you’ve ever had to do?

(Either difficult skill-wise, or difficult to emotionally bring yourself to do)

Answer 40

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Question 41

Whom among the people we know do you want to get to know better?

(It could be someone here, or someone else we all know)

Answer 41

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Question 42

With whom among the people we know do you wish you could take back a certain interaction you’ve had?

Answer 42

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Question 43

Have you ever had an epiphany? What did you realize?

Answer 43

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Question 44

Have you ever been fired from a job or kicked off a team? For what?

Answer 44

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Question 45

What’s something you believe that almost nobody you know believes?

Answer 45

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Question 46

What’s the bravest thing you’ve ever done?

Answer 46

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Question 47

What do you think people dislike the most about you?

Answer 47

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Question 48

What gives you the most anxiety?

Answer 48

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Question 49

Have you ever been to therapy? Was/is it helpful?

Answer 49

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Question 50

What’s the most difficult conversation you’ve ever had?

Answer 50

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Question 51

When you’re not around, what do you want people to say about you?

Answer 51

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