The Conversation Starter Pack (With Depth)

These aren’t your average icebreakers

If you want to actually know someone—beyond the “what do you do?” script—these questions are your golden key. Honest answers lead to real connection. You don’t need to ask them all at once, just pick one and see where it goes.

• Who do you admire, and why?

  What people praise says a lot. What people admire says more.

• What’s the hardest thing you’ve ever done?

  You’ll learn what “hard” means to them—and how they handled it.

• What are you great at? How do you know?

  Confidence meets self-awareness. This one’s revealing in all the right ways.

• What’s the most impactful thing you’ve been responsible for?

  This pulls out pride, leadership, and sometimes… big surprises.

• What are you proud of?

  Success, goodness, growth—it all lives here.

• Do you believe in a god? Why or why not?

  This isn’t about religion—it’s about how they think.

• What would your friends or coworkers say about you?

  Humble? Honest? This one reveals how they see themselves—through others.

• What would smart people disagree with you about?

  Now we’re talking spicy takes. Let them cook.

• What do you do for fun?

  Joy, rest, and weird hobbies—it’s all fair game.

• What’s something you’ve changed your mind about this past year?

  Reflection is a green flag. Growth lives in this question.

• What’s your best-case scenario?

  Dreams. Desires. Where they’re headed.

• What was your lowest point? What happened?

  Handle with care—this one holds weight. But it’s where the good stuff often begins.

• What book or essay hit hardest this past year?

  Readers reveal themselves here—and so do their influences.

• What were you wrong about recently?

  Humility is magnetic. This one tells you how open they really are.

Inspired by the Quarter-Mile blog.