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40 Questions: Conversation Starters For More Intimate Chats

40 Questions: Conversation Starters For More Intimate Chats

What if we could have more meaningful and engaging conversations more often? We've brought back a suite of questions to help amplify appreciation, intensify intimacy, and help you strengthen your connection with yourself, lover/s, friends and others. Feel free to screenshot them, print them out, or take them with you to dinner. And make sure to have fun taking turns in picking and answering the questions.


Spoiler: Not all questions are about coupling up, some of them celebrate friendship, self-love, singledom, and radical acts of connection.

Conversation Starters To Ask Yourself

  • If you could have one superpower what would it be?
  • What's your single most recurring dream/nightmare?
  • What's the best concert/exhibition/event you've ever been to?
  • What's the best piece of advice you've ever received?
  • What one thing has made you a stronger or better person?

  • Do you remember when you first masturbated? What did it feel like?
  • Which actor(s) would you choose to play each stage of your life thus far
  • What is your most beautiful memory?
  • What do you love most about yourself?
  • How do you love yourself on a daily basis?

  • Where will you take yourself this Valentine’s day?
  • What area of self-love do you want to explore next?
  • Are there any parts of your sexuality not yet fully explored?
  • What are three things on your bucket list?
  • What areas are you still learning about yourself?

  • Are there any areas that you feel like you need more support in?
  • What things help make sex great for you?
  • What do you need in order to feel heard and understood?
  • What things can you do to make others feel heard and understood?
  • What is your favourite daily routine?

  • What are your favourite types of gifts to receive?
  • What things do you love for people to do for you?
  • What are your favourite ways to be touched?

Conversation Starters To Share

  • If you could, what one person would you bring back from the dead?
  • Who do you think has had the biggest influence on the person you are today?
  • What is your favourite person’s most endearing quality that they might not see in themselves?
  • Pick a time when your favourite person really rose to the occasion.
  • What do you most admire about your favourite person?

  • When was the last time you were proud of your favourite person and why?
  • If you could take your favourite person anywhere in the world, where would you go and what would you do?
  • What attracted you to your partner when you first met, and what attracts you now?
  • In what ways has your favourite person grown over the time you've been together?
  • What are three qualities your favourite person has that makes your relationship stronger?

  • Name three of your favourite person’s favourite things.
  • What experience made you feel the most connected to your favourite person?
  • What do you feel like you and your favourite person do well together
  • What things can you and your favourite person learn together?
  • What things do you think you might need to work harder on together?

  • What’s your biggest fantasy with your favourite person?
  • What songs remind you of your favourite person?

Bonus Round Conversation Starters

  • Do you know your love languages? If so, what are they?
  • Which love languages do you wish you were better at?
  • What are your favourite types of stimulation? E.g. vibration, stroking, etc.
  • Do you have a favourite fantasy, and what first awakened it?
  • What kinds of conversations do you wish more people had more often?
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