

Conversation Starters for Meaningful Connection
Getting to know someone takes time and effort. We know it isn’t easy to truly understand someone, whether we’re trying to connect with a romantic interest, a close friend, or even a family member.
We built this list of conversation starters specifically to aid people trying to have meaningful interactions with their loved ones. These probably aren’t the first questions you would think to ask someone, and that’s the point! Our hope is that this list will help you connect by fostering vulnerable and important conversations that will help you walk away feeling closer than ever.
And as always, we extend a friendly Chatterbox invitation to upvote your favorites!
- What seemingly insignificant thing contributes greatly to your happiness?
- What moment do you wish you could relive and even change?
- Where do you need to be thinking bigger?
- How are you creating a life well lived?
- What do you have absolute faith in?
- What part of your life have you still not figured out?
- If you could only hold onto five physical items, what would you keep and why?
- What would you refuse to give up even if you were offered $10 million?
- Where in your life are you making unhelpful assumptions?
- What are your core values?
- Which friend would you call to help you bury a body and why?
- Where in your life are you lazy and what’s your excuse?
- What would you hope would be said in your eulogy?
- What was missing from your childhood?
- What widely accepted belief needs to be dead and buried?
- What groups do you have a negative bias towards?
- Describe a time in your life when the phrase “when it rains, it pours” applied.
- Would you rather win $1 million or earn $1 million?
- Where are you playing it too safe?
- What do you do better than anyone you know?
- If people came with a warning label, what would yours be?
- Where in your life are you living in a bubble?
- Describe a time when you were your own worst enemy.
- Describe your relationship with your father in one sentence.
- Where in your life do you feel misunderstood?
- If you could time travel back to an earlier time in your life, where would you visit and what would you do?
- How do you best receive criticism?
- What act of self-care should become a non-negotiable in your life?
- If someone wanted to annoy you easily, what would they have you do?
- Which teacher had the biggest impact on you and why?
- What would you like to re-experience because you did not appreciate it fully the first time?
- What do you think you’ll regret not doing when you’re on your deathbed?
- Where are you settling when you could be thriving?
- Fast-forward twenty years…what does your life look like?
- If you met your hero, what question would you ask?
- If you had to switch places with another person, who would you choose and why?
- What have you done in the last six months that you are proud of?
- How do you imagine that you’ll spend your retirement?
- What kind of mentor do you need to help up level your life?
- What historical event do you wish you’d experienced first hand?
- What part do you want to play in solving a global program?
- What skill do you need to acquire to achieve your next goal?
- Where are you falling short of your potential?
- In what ways are you bad with money?
- What’s a dealbreaker for you in a relationship?
- How has inaction impacted your life negatively?
- What’s your social media weakness?
- What is the saddest memory from your childhood?
- What affirmation do you need to wire into your programming?
- What beliefs keep you from getting into trouble?
- What do you think society owes its citizens?
- What’s your North Star?
- What is your definition of success?
- What is the last thing you changed your mind about and why?
- What do you think is the most damaging modern industry and why?
- What beliefs have you adopted from other people that don’t serve you now?
- What decision are you grateful you didn’t make?
- What’s the best mistake you ever made and why?
- As a child, what rules were made to be broken?
- What choice has had the greatest impact on your life?
- If you could only leave your children one life lesson, what would it be?
- What are the daily rituals you swear by and think everyone else should explore too?
- Describe a time you achieved what you were striving for only to feel disappointed by the success.
- What have you learned about love?
- What is the best advice you received from your mother?
- What controversial opinions do you enjoy sharing with others?
- What compliments do you struggle to believe?
- What would it take to remove the biggest obstacle between you and your goals?
- What do you want to know about someone that you’ve been scared to ask?
- Describe a time or situation in which you felt screwed over. How did you respond?
- Who is the strongest person you know and how do you wish you were more like them?