The one thing you’ve been wishing for.

Knowing how to have a deep conversation isn’t easy. That said, talking about deep topics – rather than small talk – is crucial to maintaining an intimate connection. In an experiment, social psychologist Arthur Aron found pairs who discussed ‘deep questions’ were much more likely to maintain their level of connection than those who kept to small talk.

The one thing you’ve been wishing for.

Knowing how to have a deep conversation isn’t easy. That said, talking about deep topics – rather than small talk – is crucial to maintaining an intimate connection. In an experiment, social psychologist Arthur Aron found pairs who discussed ‘deep questions’ were much more likely to maintain their level of connection than those who kept to small talk.

  • What do you miss about being a kid?
  • If someone gave you enough money to start a business – no strings attached – what kind of business would you want to start and why?
  • If you could go back in time, what’s one piece of advice you’d give to your younger self?
  • Tell me three things that happened in the last week that you’re thankful for.
  • What’s your favorite memory we’ve shared together? Gimme as many details as possible.
  • What makes you happy?
  • Who or what has changed your life?
  • How do you best connect with others?
  • Are you a giver, a taker, or a matcher? Are there areas in your life where you act like one type, and other areas where you act like another?
  • What matters most to you?
  • What’s some of the best advice you’ve ever gotten?
  • If you could take a year-long paid sabbatical, what would you do?
  • Who do you trust?
  • What are five things you’re thankful for right now?
  • If a genie granted you three wishes right now, what would you wish for?
  • What’s the craziest thing you’ve ever done and would you do it again?
  • What’s your favorite family tradition?
  • If you could enter a time machine, what time period would you go to?
  • What’s your favorite quote?
  • What do you value most in a friendship?
  • Tell me your life story in four minutes, with as many details as possible.
  • What’s something I’ve done for you that you’re grateful for?
  • What do you want your legacy to be?
  • What are your biggest goals for this year? How will you work to achieve them?
  • Where was your favorite place to go as a child and why did you love it there?
  • What was the first thing you bought with your own money?
  • What are you curious about?
  • Name four things we have in common.
  • What are your favorite three topics to talk about?
  • What’s your earliest memory?
  • In what situations do you feel most comfortable sharing your perspective?
  • Who’s someone you really admire?
  • What would you do on your “perfect” day?
  • If you had €100,000 to give away to any cause, which cause would you choose and why?
  • Where are the top three places you want to travel to some day, and why?
  • Tell me about a day you had that you’ll never forget.
  • If there were 26 hours in a day, what would you do more of?
  • Is there something you’ve dreamed of doing for a long time? Why haven’t you done it yet?
  • What moments or events during your childhood shaped who you are now?
  • What do you think about most?