75 Deep Conversation Starters That’ll Help You Bond for Real

Not everyone is an open book, willing to share everything about themselves right off the bat. In fact, we’d wager that *most* people aren’t going to spill their deepest feelings the first time you meet. Getting to know someone is a process, and when you’re building a meaningful relationship—whether platonic or romantic—it’s not one you really want to rush. Taking it slow and asking the right questions is key to building trust and making someone feel comfortable enough to open up and bond, which is why we put together this helpful list of deep conversation starters. When you both feel ready (so like, maybe not the first conversation you ever have, ya know?), pull these out and get talking.

We’ve also included tons of deep questions to ask people who have already been in your life for awhile, including partners and friends. No matter how well you think you know someone, people always change with time. Your significant other might not be the same person now as they were five years ago. And when was the last time you had a meaningful check-in with your best friend? It’s so important to keep talking, so that you can make sure all of your relationships stay healthy and happy. And when you’re struggling to break through or resolve an argument? We’ve got some helpful conversation starters for that too.

A few basics before you get started: Make sure you read the room. You never want to make anyone feel uncomfortable or like they’re being questioned. If someone doesn’t want to open up (these are deep conversation starters, after all), don’t pry, and give them some space. Everyone moves at a different pace! It’s also important to remember that everyone’s life and experiences are different. There might be some topics you’re eager to chat about but that the other person doesn’t want to touch, and that’s okay! Try not to take it personally, because chances are, it’s not about you, and they’ll open up when they’re ready.

Now, without further ado, here are 75 deep conversation starters that’ll help you really get to know someone, or dig deep and bond with a friend, family member, or partner.

Deep Conversation Starters for Someone New

  1. If you could live anywhere in the world, where would you live?

  2. If money were no object, what would you do for a living?

  3. Is your current job what you always dreamed of doing?

  4. What’s your relationship like with your parents?

  5. Do you have any siblings? What’s your relationship like with them?

  6. Who is your hero?

  7. Who do you think knows you better than anyone else?

  8. If you could invite any three people over for dinner, living or dead, who would you invite?

  9. Who is your best friend? How did you meet them?

  10. What’s your happiest memory?

  11. What’s the most beautiful place you’ve ever been to?

  12. Tell me about your most embarrassing moment.

  13. What are your hobbies, and why do they matter to you?

  14. What’s your most prized possession and why?

  15. Have you ever seen a movie or TV show, or read a book that you really identified with? Why?

Deep Conversation Starters for a Date

  1. What kind of relationship are you looking for?

  2. What about me made you want to swipe right? (Or ask me out—depending on how you met.)

  3. Tell me about your last relationship.

  4. Why did your last relationship end?

  5. What qualities do you think make a good partner?

  6. Tell me about the best date you’ve ever been on. What about the worst?

  7. Where do you see yourself in five years?

  8. What are your thoughts on marriage?

  9. What about children?

  10. What’s your love language?

  11. What do you think makes us compatible?

  12. Tell me about your first kiss.

  13. Who was your first crush?

  14. Have you ever cheated or been cheated on?

  15. Are there any questions you’re too nervous to ask me?

Deep Conversation Starters for a Partner

  1. What do you love best about me?

  2. When did you first realize you were in love with me?

  3. What do you love most about our life together?

  4. What is your favorite date we’ve ever been on?

  5. Is there anything about our relationship that you wish were different?

  6. How do you feel when we fight?

  7. How do you feel about our communication habits?

  8. What can I do to be a better partner to you?

  9. Are we still aligned on our vision for the future?

  10. Is there anything you wish I knew or understood better about you?

  11. What’s the hardest thing we’ve gone through together?

  12. How do you see our relationship changing in the next five years?

  13. Is there anything you learned from your parents or relatives about love and family?

  14. Are you happy with our sex life?

  15. Is there anything we haven’t tried in the bedroom that you’d want to?

Deep Conversation Starters for a Friend

  1. What do you love most about our friendship?

  2. When did you know we’d be great friends?

  3. Is there anything about our friendship that you would change?

  4. Have I ever done anything to upset you that you didn’t address with me at the time?

  5. How can I be a better friend to you?

  6. What’s the happiest memory you have of our friendship?

  7. Do you feel like I really listen to you?

  8. What do you think makes us so compatible as friends?

  9. What moment between us has made you laugh the most?

  10. Have there been any moments between us that have ever made you sad?

  11. How do you describe our friendship to others?

  12. Is there anything you’ve learned from me?

  13. How do you see our friendship changing in the next five years?

  14. Do you think we’d be able to maintain our friendship if we didn’t live in the same town?

  15. Do you think we’d be as close as we are now if we had met at a different time in our lives?

Deep Conversation Starters to Resolve an Argument

  1. What about this situation makes you angry?

  2. What prompted this argument?

  3. What are you really trying to say?

  4. What do you need from me to make you feel supported and heard?

  5. This issue is important to me too. How can we reach a compromise?

  6. Do you feel like we’ve been in this situation before?

  7. What can we do to resolve this once and for all?

  8. Is there something we can do long-term to solve this issue?

  9. Is there anything I can do to communicate better when we argue?

  10. Is there something we can do on a regular basis to improve our communication habits?

  11. Do you think our conflicts make us stronger?

  12. What argument are you glad we had?

  13. Is there anything that you regret saying to me?

  14. Is there anything we haven’t addressed or gotten out right now?

  15. What’s the most loving, compassionate way we can put this behind us?

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