27 thoughtful questions for deeper conversations

A couple walks hand-in-hand while each holding coffee cub. The cobblestone street is covered with autumnal leaves.
The Seattle Times suggests replacing common conversational questions with more thoughtful ones to foster deeper connections. Instead of "How are you?" ask about joy; explore favorite spaces at home instead of origin; inquire about childhood pastimes, preferred research topics, and personal aspirations to describe upcoming months. Emphasize self-reflection and understanding in relationships, touching on topics like new passions, confronting unexpressed truths, and the impact of societal issues. Encourage sharing personal learnings, unchanged attributes, and self-consistency to nurture closeness and self-discovery.

From the 2024 Feb 02 Seattle Times.

Unique alternatives to go-to questions that can sometimes feel tired

  • Instead of asking “How are you?” ask “What’s bringing you joy lately?”
  • Instead of “Where are you from?” ask “What’s your favorite room or space in your home and why?”
  • Instead of “Tell me about yourself” ask “What did you love doing as a kid that you don’t do anymore?”
  • Instead of “What do you do for work?” ask “What topics could you research for hours?”
  • Instead of “Anything exciting coming up?” ask “What are three words you want to describe the next three months of your life?”
  • Instead of “What do you like to do for fun?” ask “Tell me the details of your ideal day?”

Closeness-generating questions

  • Is there a new joy or passion in your life that you rarely talk about?
  • What’s one thing you’ve always wanted to do but haven’t done? What stops you?
  • When was the last time you did something for the first time? What was it? 
  • When was the last time you cried? What was it about?
  • How would you act if you lived a life more true to yourself, not what others expected of you?
  • Is there a truth that you are holding back from expressing? Would you be willing to tell me?
  • What are your experiences of having or not having power in relation to race, class, gender, sexual orientation, other (specify)?
  • What unresolved situation or relationship takes up space in your mind, and how might you seek resolution?
  • How is our divided, troubled world impacting you, and how do you try to stay compassionate and engaged?
  • What do you appreciate about the person you’ve been sharing with?

Skip the Small Talk questions

  • What’s something you’ve learned from a past friendship or romantic relationship that’s stuck with you?
  • What are some open questions in your life right now? How are you going about answering them (or coping with having them unanswered)?
  • What is at least one thing about yourself that you wish more people knew about you?
  • What are a few things that you love about your life as it is right now? Or if that feels too difficult, what sorts of things are helping you cope with the unpleasant things in your life right now?
  • Describe the kind of person you would like to be. What things are you already doing that are consistent with that version of yourself?
  • What are some things about yourself that you hope never change?
  • In what ways are you different from the way you were five years ago? How about 10 years ago? In what ways are you the same?
  • When do you feel most like yourself?
  • Tell me an anecdote of you as a child that’s somewhat representative of who you are today.
  • What personality strengths have your childhood caregivers helped you develop, be it intentionally or unintentionally? What strengths have you cultivated on your own?
  • What are some of your biggest hopes for your (personal) future?
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