Intimacy-building questions for each type

How can you get someone to open up to you? To feel safe, unjudged, and appreciated? We’ve compiled some questions you can ask each Enneagram type, which are likely to get their minds churning and perhaps even feel closer to you after sharing.

 

Ones

1s tend to love sharing their opinions on moral dilemmas, philosophy, or wisdom. They may not want to get too personal too quickly, but they do enjoy real talk and reflection.

• What is the most significant thing you’ve ever changed your mind about?
• How do society’s morals differ from your own?
• What book dramatically changed your life?
• What behaviors or traits in another person really drain your energy, and why?
• When was the last time you took a risk that paid off?

Twos

2s are used to asking others all about themselves — surprise them by showing genuine interest in their unique selves, too. Try to avoid topics that could make them feel shame, and do really listen.

• What is something you feel that people expect from you that you’d prefer never to do again?
• What is the best gift anyone has ever given you?
• Which celebrity would you most like to meet? Why?
• What are your simple pleasures?
• Which one of your beliefs would be the most difficult to change, even in the face of overwhelming evidence?

Threes

3s are competent conversationalists, but they may lean heavily into small talk and topics that are “safe.” Try to get them to open up a bit and accept them fully for whatever they choose to share.

• What respected public figure do you think is overrated, and why?
• What is the best advice you’ve ever received, and why did you need it?
• What’s something you’d want to wear if no one would judge you negatively for it?
• In what ways do you hold back or water down who you are or how you act?
• What is your most treasured memory?

 

Fours 

4s are notoriously sensitive and thoughtful. If you ask them a deep question and give them space to answer it, you’ll likely be pleasantly surprised how quickly they’re willing to connect at that level.

• What have you lost that you would like to find?
• What difficult or painful experience would you recommend to everyone?
• What is the most stable part of your identity today, and what is the part that’s most in flux?
• Do you have any superstitions?
• What is something that’s meaningful and noticeable to you in the world that you wish more people would recognize?

Fives

5s can be quirky and/or shy. Don’t let that fool you; they’re oftentimes a well of deep thoughts and ideas. They’ll usually happily engage on interest areas and hypotheticals.

• What’s something that you think people assume about you that isn’t true?
• If you could have instant brilliance in one specific subject, what would you choose?
• If you see one measurement or statistic over everyone’s heads, what would you want it to indicate?
• What’s the hardest thing you’ve ever done?
• What’s the most interesting research rabbit hole you went down?

Sixes

6s blend fascination with people, principles, and analyses. As Thinking types, it’s just a matter of finding the right question and being safely receptive to them…and they’ll be off to the races!

• What was the most difficult thing you’ve ever had to do?
• What are you proudest of yourself for getting through over the past year?
• Describe what your inner monologue sounds or looks like.
• Which group is larger: people who trust you, or people you trust?
• What is the strongest obligation, if any, that you believe you have?
  
  

Sevens

7s tend to not have a problem with shyness. Get their mind hooked with a fun “what if” or intellectual idea, and within 60 seconds you’ll have them in flow.

• What relatively common experience have you never had?
• If you had to get a tattoo, what would you get and where would you put it?
• What are you currently working through that people don’t see?
• Would you prefer to date someone 20 IQ points higher or 5 points lower than you
• How will our culture change most in the next 100 years?

Eights

8s prefer real talk, real quick; no need to beat around the bush with them. Don’t expect them to share vulnerabilities with you, but do be sure that they’ll tell you what they really think.

• What is the “elephant in the room” that no one is talking about, but should?
• If you could fix one weakness in the population, what would it be?
• What groups or communities are you most judged for being a member of?
• When was the last time you felt misunderstood by someone?
• What do you wish they knew?
• What vulnerable or emotional thing would you like to express but have trouble sharing?

Nines

9s may seem simple and agreeable if you don’t know them well; they are far deeper than you think. Don’t pressure them too much if they don’t want to talk, but float a few questions by them, give your undivided attention, and see what happens.

• Do you have more thoughts or feelings?
• How would you raise a child differently from how your parents raised you?
• What viewpoint is the most difficult for you to empathize with?
• If you could ask the universe one question and get the truth, what would you want to know?
• What’s an opinion that matters to you more than you let people see?

Enjoy!!