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MBTI

Enneagram Conversations

Head, heart, or gut - and what that means for how you love.

30 questions10 light · 10 medium · 10 deep

Cuper angle: The Enneagram maps core motivations, not just behavior. Knowing whether someone leads with fear, image, or desire tells you more about conflict patterns than almost any other framework.

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Do you know your Enneagram type, and does it actually sound like you?

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All 30 Questions

1

Do you know your Enneagram type, and does it actually sound like you?

2

In general, do you lead with your head, your heart, or your gut?

3

Do you find it easier to trust your instincts or to think things through carefully?

4

When something goes wrong, is your first response to fix it, feel it, or figure out why?

5

Are you more motivated by fear of failure or by hope for something better?

6

Do you tend to push people away when you're overwhelmed, or pull them closer?

7

What's something you're quietly proud of that you don't usually talk about?

8

Are you better at starting things or finishing them?

9

Do you find it easier to act, feel, or think your way through a hard situation?

10

What's something you've actively worked on about yourself that used to hold you back?

11

Out of nine motivations - reformer, helper, achiever, individualist, investigator, loyalist, enthusiast, challenger, peacemaker - which resonates with you most?

12

What's something you do when you're stressed that you know isn't actually helping?

13

What's a core fear that shows up quietly in your relationships?

14

When things get hard, do you tend to seek control, attention, or safety?

15

What's the thing you work hardest to protect about yourself?

16

Do you tend to adapt to people, confront them, or withdraw from them when something feels off?

17

What does your inner critic say most often, and where do you think it learned that?

18

What's something you do out of habit in relationships that doesn't actually serve you?

19

Are you more afraid of being abandoned, of failing, or of being controlled?

20

What does growth look like for you personally - and is it usually comfortable or uncomfortable?

21

What's your core motivation in relationships - to be needed, to be admired, to be understood, or to feel safe?

22

Is there a pattern in your life that looks like a strength on the outside but is actually a way you protect yourself?

23

What's something you've never been honest about wanting from a relationship because it felt like too much to ask?

24

What are you most afraid people would see if they really looked at you without the edit?

25

What do you think you've given up to be lovable or acceptable, and was it worth it?

26

Is there a version of yourself you'd be if you stopped managing what other people think of you?

27

What does it feel like when your core need goes unmet in a relationship, and what do you do with that?

28

What's something about how you love people that you wish they understood without you having to explain it?

29

Do you think you're aware of your own patterns, or do you mostly notice them in hindsight?

30

What would it mean to you to be fully accepted as you are, without needing to manage or adjust anything?

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How to use these

1

You don't need to know your Enneagram type for these to work - just answer honestly.

2

Pay attention to what they say their core fear is; it shows up in relationships.

3

The triad questions (head, heart, gut) are a shortcut to compatibility data.

4

These questions get better the more self-aware each person is - that's data too.

Turn questions into connection

Cuper uses MBTI, attachment style, and Enneagram to surface the right questions for your personality pairing, in the app, with your match.

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