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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 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.


Many of us spend our lives meeting, loving, and living with people we barely know. We're here to help change that with more engaging conversations.


Not all of the following conversation starters are about coupling up, some of them centre conversations around friendship, self-love, singledom, and promote 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 in a conversation?
  • What one thing has made you a stronger or better person?

  • Do you remember when you first masturbated, and what it felt 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 would you take yourself on a solo date for Valentine’s Day?
  • What area of self-love do you want to explore next?
  • What parts of your sexuality are 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?

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?
  • Can you name a time when your favourite person really rose to the occasion, and why?
  • 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?

  • Can you name three of your favourite person’s favourite things?
  • What experiences/conversations 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?
  • 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?

Bonus Round Conversation Starters

  • Speaking of conversation, do you know your love languages? If so, what are they?
  • Which love languages do you wish you were more fluent 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?

Had your share of meaningful conversations?
Please feel free to share your most helpful conversation starters and questions in the comments below.

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