48 Deep Conversation Starters To Know Someone Better


conversation starters

Human personality operates on a very wide spectrum. We all have a lot of layers to our personality. We have to use great conversation starters to dive deep and uncover the layers of their personality to reach to their core, to know him/her.

But in today’s fast paced digital life, we mostly end up having surface level communication that doesn’t go beyond surface level conversations like what’s up. As we don’t engage in deep conversation, most of our friendships and acquaintances are operating on a very superficial level.

Just when we think we know a person, we are surprised with more revealing facts as we explore deeper.


We are perpetually faced with a paradox. We have a staggering number of friends and followers online but very few deep, authentic, intimate and fulfilling relationships in real life.

If we want to do away with this paradox, we will have to make the time and effort to get to know someone on a deeper level that go beyond the surface.

Read 10 Questions To Ask To Go Deep In Your Relationship

This definitely cannot be attained by using surface level conversations about the weather or latest fashion trends.

So here’s, a list of interesting conversation starters are compiled which can help you forge deeper and intimate connections with someone.

1. TOPIC – Metaphysics

Some of the most interesting questions that can take you beyond the surface level conversation and open up your horizon to the whole wide mysterious universe out there fall under the category of Metaphysics.

The term Metaphysics is a combination of two words “Meta”+ “Physics”. Here, Meta means over and beyond. So, the term implies over and beyond physics.

Metaphysics is the branch of philosophy that is concerned with understanding the essence and fundamental nature of things and principles that organize the universe.

It is concerned with questions like “What is the nature of reality?”

It comprises of all things abstract and intriguing like questions about life and death, parallel universes, alternate reality, time and space etc.

Here are few sample Metaphysics questions that you can try on to get started:

  • Are you the same person you were yesterday?
  • What is your notion of time? Are we affected by it, or does our consciousness create it?
  • Do you believe in other dimensions or parallel universes?
  • Where do we come from and what happens to us after physical death?
  • Are there an infinite number of realities beyond our own where each possible decision taken is a different fork in the road traveled down?
  • Do you believe in Déjà vu or synchronicity? Have you ever experienced it?
  • Do you think that our mind just observes reality or can mind also alter reality?
  • Do you think we create our own destiny or are we governed by fate?
  • Do you believe in Out of Body or Near Death experience? Have you ever experienced anything like this?

The second categories of questions that can help you understand someone on a deeper level fall under the bracket of Love and romantic relationships.

2. Topic – Love

Love is the most sought after and yet most elusive human emotion.

We are mostly carrying unhealthy definitions of love from childhood fairy tales and Hollywood flicks.

The most common misconception propositioned by Hollywood flicks and childhood fairy tales about love is the notion that dependency is love.

In the romantic love ideal propositioned in these fairy tales, the delicate balance between intimacy and interdependence is lost and love borders on the psychological condition of codependency.

If we really want to forge a deep, authentic and intimate connection with someone, we have to be willing to have deeper conversations. This will help us find out if we are on the same page with the other person as far as our definition of love is concerned.

Here is a list of conversation starters that can help you to understand someone’s definition of love better:

  • Does being in love mean being independent, codependent or interdependent for you?
  • Is love only a bio chemical response to specific set of stimuli?
  • Is love a choice or a feeling?
  • Do opposites attract or are like minded people more compatible in relationships?
  • If you have to rank in order of preference: physical attraction, emotional compatibility, intellectual compatibility and lifestyle compatibility? What would be your order of preference?
  • Should you change yourself for someone you love?
  • Can you love more than one person at the same time?
  •  Is it important to be best friends with your romantic partner?
  • What is the most thoughtful gift that you have ever received or given?
  • What’s your take on the forever and happily ever after?
  • What’s the craziest thing you would do for someone you love?
  • What is your love language? How do you express love and how do you want your romantic partner to express love to you?
  • When you are feeling low, do you prefer to be left alone or would you like someone to cheer you up?
  • Why do you think your past relationship ended? What did your past relationship teach you?
  • Do you usually remain friends with your exes?
  • Do you believe in a thing as soulmate, twin flames or kindred spirit?

3. Topic – Psychology

Psychology is the study of the human mind and behaviour.

It includes the study of the conscious, unconscious mind and thoughts, feelings that lead to specific behaviors and traits that distinguish one person from the other.

Here is a list of interesting conversation starters that can help you to understand how someone’s brain is wired and why they do what they do:

  • Nature or nurture-Which one do you think plays a bigger role in shaping one’s personality?
  • Does happiness lie in the journey or the destination?
  • What is your most vivid memory from your childhood?
  • What are your three biggest fears?
  • What are you three biggest achievements?
  • Who is your personal hero and what do you admire most about them?
  • Do you like to spend time alone or in groups?
  • Do you like to explore new things or do you like to follow routine?
  • What do you think about when you’re by yourself?
  • What’s the most spontaneous thing that you have done in life?
  • What’s the biggest risk that you have taken in life?
  • What is the darkest thought you’ve had and what is the darkest thing you’ve never shared with anybody?
  • What makes you feel anxious or overwhelmed?
  • What place or activity makes you feel calm and serene?
  • Which is your favorite book, quote or poem and why do you relate to it? Which is the book or movie track or scene that brought out the most emotions in you?
  • Is home for you a place or a feeling? Describe that place or feeling?
  • Out of the entire range of negative emotions of anger, jealousy and insecurity and greed, which one affects you, the most?
  • Out of the entire range of positive emotions like love and compassion, calmness, enthusiasm, which one is your biggest asset?
  • What trait do you admire the most in others and what trait you cannot totally stand?
  • If you had to describe yourself without mentioning your looks, profession or past, how would you describe yourself?
  • Do you usually go with your gut instincts or your brain?
  • What’s your biggest goal in life right now and what are your goals for next five years?

So, here you go, go ahead and try these questions and see the sparks fly.

If you want to go a little deeper and forge deep intimacy, you can also try the 36 questions for social experiment with your partner.

These questions are designed by Social Psychology researcher Arthur Aron of the Interpersonal Relationships Lab at Stony Brook University in New York. Link HERE

You can try these conversation starters with your date, friends or even long term partners to deepen the intimacy.

Deep Conversation Starters To Know Someone Better
48 Deep Conversation Starters To Know Someone Better
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