Good Questions to Create Friends

I didn't write the following-- looks like AI, but I think it does a good job of getting us thinking about two things in the end: 

clarity around your circle of interests

and within that circle, what your smaller circle of influence is within that larger circle of interests. How do they do that? By opening yourself up to others, your mind loosens its grip on all the reasons you can't do that next big thing, the change in relationship, leave work, start a business...start working out. Run through these questions with someone you just met or a friend, and watch how your own mind feels after a conversation.

And these questions are a  great way to nurture conversations with friends: 

Here are 10 questions that work like social superglue. Each comes with a quick breakdown of why it works, and how to use it.

• “What’s something most people misunderstand about you?”

  • Why it works: People LOVE feeling seen and understood. This question gives power. It invites someone to gently correct the story others assume about them.

  • Science behind it: Harvard psychologist Dan Gilbert’s research on self-concept shows people enjoy explaining their inner self when they feel safe.

  • Pro tip: A great follow-up is, “Has that always been the case, or did something shift over time?”

• “What’s a weird childhood obsession you had?”

  • Why it works: Nostalgia + playfulness + vulnerability. The trifecta.

  • Referenced in: Dr. Laurie Santos’ Yale course on the science of well-being. Childhood memories trigger high dopamine recall and bonding.

  • How to use it: Great for transitioning from surface talk to deeper vibes. Light and funny but still human.

• “When you’re feeling overwhelmed, what’s your go-to move?”

  • Why it works: This reveals emotional regulation style. Are they avoidant? Problem-solvers? Escapists?

  • Backed by: The Gottman Institute’s emotional intelligence research. Understanding someone’s stress response is a shortcut to knowing their values and personality.

  • Watch for: How much self-awareness they show. Says more than the answer itself.

• “What’s a belief you’ve changed your mind about recently?”

  • Why it works: This shows growth, open-mindedness, and gives a peek into how their worldview evolves.

  • Referenced in: Adam Grant’s Think Again which emphasizes the power of cognitive flexibility.

  • Bonus power: It signals YOU are also open-minded. Non-judgmental. Safe space.

• “What’s something you’re proud of that you don’t talk about enough?”

  • Why it works: It invites quiet confidence. Not the performative résumé stuff.

  • Research: Brene Brown’s work on shame and vulnerability shows people often hide pride because they fear judgment. This gives permission.

  • Timing: Use this after 20–30 minutes of conversation for deeper connection.

• “If your 15-year-old self could see you now, what would they think?”

  • Why it works: Combines self-reflection, time travel, and identity. How people answer shows regrets, pride, expectations, and goals.

  • Used by: Therapists and coaches to track personal narrative.

  • Optional angle: “What would they be surprised by?” is a softer version.

• “What’s one thing you secretly wish more people asked you about?”

  • Why it works: It flips the script. Lets them drive the convo.

  • Study link: A 2022 Journal of Personality and Social Psychology article noted people feel most connected when they feel invited to express, not forced.

  • Use it when: You sense someone has depth but isn’t sure how to share it.

• “What’s something you’ve learned the hard way?”

  • Why it works: Honest. Direct. A little raw. But not intrusive.

  • Backed by: Stanford’s neuroscience research on storytelling and meaning-making. Sharing adversity leads to oxytocin release, aka the trust chemical.

  • Tone tip: Keep your energy calm and respectful. Don’t rush it.

• “Who in your life makes you feel the most like you?”

  • Why it works: This reveals closeness, psychological safety, and how someone defines authentic self.

  • From: Esther Perel’s podcast “Where Should We Begin?” She uses versions of this to help couples reconnect.

  • Great follow-up: “What do they do that makes you feel that way?”

• “What kind of person do you want to be remembered as?”

  • Why it works: Legacy + identity + aspiration. A future-self question loaded with meaning.

  • Referenced in: The “End-of-life reflection” exercises in Designing Your Life by Bill Burnett and Dave Evans (Stanford design lab).

  • Use with care: Best used after you’ve already made some emotional ground.

If you want to build fast trust, go deep without going weird. People are dying to talk about stuff that matters, but most convos never go there. These questions open the door.