70 Thought-Provoking Questions (Conversation Starters)
here’s where it all started
It was nighttime, the tasks of the day were done - shoes were kicked off, and my guy and I were sitting down watching a documentary - The Skin Deep. There was a question asked that was so unexpected, that it almost took my breath away.
The question was somewhere along the lines of - “what’s the pain in me you wish you could heal?”
Now, me and my guy - we’ve been through some things; so that question opened up a night of vulnerability + deep insight. The answers to that question (from both sides) were unexpected and really beautiful.
And not only that, I believe the conversations that started from that question were “in essence” - what we are all looking for.
That rawness + honesty + deep connection.
We crave it, and sometimes we forget our ability to create it. We forget that we can:
Create the atmosphere for the truth + connection.
Tune into what’s being asked of the moment.
Reach out and share our thoughts with someone we trust.
Ask thought-provoking questions.
We’re desiring intimacy and the answer to that is to go deeper.
I know how scary that can feel at times, but real depth, truth, and love is safe. There’s no threat in it. It’s just meeting the moment as is - and being willing to open, to hear, to give, and then receive.
With that said, the 70 thought-provoking questions below were inspired from me envisioning nights of connection, truth, and rawness. What’s revealed when you’re really open can be transformative and healing. So be sure to tap into this list with someone you love & trust.
📍 Here are 70 thought-provoking questions (conversation starters)
What’s the best question you’ve ever been asked?
Who’s the most influential person in your life?
Where would you be if you hadn’t followed your dream?
What’s the best decision you’ve ever made in your life?
What’s your deepest regret and how can you forgive yourself or make amends?
What interests you about the person sitting across from (or next to you)?
If you could change one thing about the world, what would it be?
If you could bestow a superpower on your child (or a loved one), what would it be?
What’s your biggest pet peeve?
What’s a red flag about you?
What’s a green flag about you?
What color are you (in mood or feeling) and why?
What helps you breathe easy?
What do you have faith in right now?
What’s changing in your life (for the better)?
Who’s the most joyful person you’ve ever met?
What’s been the best moment of your life so far?
Do you believe in second chances?
What’s something the person across from you doesn’t know about you?
If you could teleport to any location, where would it be?
Are you honest?
Are you going through anything the person across from you doesn’t know about?
Who do you trust most in life?
What’s the most important characteristic you look for in a partner?
What’s most important to you right now?
What question can’t you seem to find the answer to?
What’s the biggest “what if” in your mind? (from ourmindfullife.com)
Who’s the one who got away?
What’s the first thing that comes to mind when you think of success?
Past or present is there someone you wish you made amends with? If so, who and why?
What’s the question you want to ask most? To whom and why?
Who is someone you wish was still around?
How have you shown up for yourself lately?
What’s your worst tendency?
What’s your best quality?
What’s your superpower?
What’s the superpower of the person across from you?
If you could receive closure from one person, who would it be?
Are you resisting change? If so, why?
In your own words, what does love mean?
In your own words, what does self-worth mean?
Have you made space in your life for what you want?
What’s a moment you will cherish forever?
Do you have feelings for anyone that others don’t know about?
If you could tell your childhood crush one thing, what would it be?
How do you handle anger?
What’s special about this moment?
What’s been the miracle in the mundane for you lately?
Where have you felt most rejected?
Where have you felt most accepted?
What have you learned about yourself in the past year?
What about yourself do you have trouble acknowledging?
What has been your most valuable life lesson?
How do you reconnect with yourself after loss?
What do you need most right now?
What are you looking forward to?
Who always has your best interest in mind?
If you could give someone a star on the Walk Of Fame in your life, who would it be?
What scares you the most?
What’s the most sacred thing about you?
What life lesson have you learned the hard way?
What makes you stand out in the crowd?
What’s something that shocked you about the person sitting next to you?
What’s been your biggest challenge in life and how did you overcome it?
What shocks you about yourself?
Is there a dream you’re hiding from others?
If you could adopt another perspective about life, what would it be?
If you could ask God, Life, The Angels, or Powers That Be any question (and receive a direct answer), what would it be?
What’s one thought-provoking question you would ask? Ask it.
What wish came true when you met the person next to you?
save for later
📍 some tips for getting the most out of these thought-provoking questions
The questions are already deep, but here are some tips to help keep the conversations going and to enjoy the experience.
Remain Open
If you approach this list with an open heart, there’s no doubt in my mind that you’re going to give and receive some eye-opening answers.
trust your insight
You’ve walked through this life experience, and all of it is stored somewhere in you as a memory, as an imprint or impression, as a feeling or a story. So when asked the questions - take a moment or two, feel into it, and answer honestly. You may also be inspired to ask another deep question - trust that.
share the experience with someone you Love & trust
Before diving into this, make sure you’re inspired to go here. Make sure the person that you’re with seems excited to answer the questions too. The best results will most likely come from two people (or a group of people) who really want to hear and understand each other.
try not to judge the answers
If you approach this experiment through the lens of curiosity and wonder, you’ll really be able to tap into the true purpose of these questions. If things get intense just remind yourself that you’re there to understand, support, and be seen as well.
well, there you have it - some questions to inspire those deep conversations
Come back to this list anytime you’re called to it.
The Skin Deep documentary inspired the conversation that night. It is a beautiful example of what can happen when you remain open + connect deeply with someone you love.
Here is one of my favorite conversations from that documentary.
You never know what truth will reveal itself when it’s given the environment to come forth. So many other conversations can also bloom from these seeds, so if it feels right to you - go there. With your loved ones (of course), and enjoy where it takes you.
Live Well & Keep Creating!
P.S. Share Your Insight: Let Me Know In The Comments Below Which Conversation Starter Resonates The Most? + Who Are You Inviting To Explore This List With You And Why?
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