20 Deep Questions Will Strengthen Your Most Cherished Relationships

What do you actually mean when you say you know someone really well? 

Jess works at the Supermarket, drives a Toyota, loves Chinese food and has three brothers. 

Think you’re close?

Have you considered going beyond the small talk? 

Has Jess ever experienced heartbreak? How would Jess react if she lost her job? How much support will she or won’t she need? Will it affect her in the long-term? 

Don’t be afraid of deep conversation.

Regardless of the basis of your relationship, deep questions will make or break your bond, and we believe it’s worth taking the risk and having these conversations. Why? Trust realised can be very powerful and establish lasting compatibility and comfort within one another. 

Having a deep connection with someone allows you to bring as much as you possibly can to the relationship, so all parties are willing to jump into the other and know when to do it. These bonds aren’t specific to couples. They are just as important to form among friends, peers and families – within groups and one on one.

Fact. Every human being’s life is different. 

When you think about all the experiences you’ve had, combined with your strengths, weaknesses and values, there’s a whole lot to be discovered and explored through conversation. Everybody grew up in a different home, different location and different school. They had different friends, different parents, split families, varying wealth and so the list goes on. 

Your own experiences have been irrespective of other people you now know, so imagine the unique perceptions you’ll have when it comes to life and values. You want to know about it, right? Tip. If you don’t, you may want to reconsider the relationship. 

Fact. Deep questions reveal possibilities. 

The simplest questions can have very revealing responses as each one unveils a series of possibilities for both you and the other person. You might find a potential partner more attractive, be inclined to practice more compassion towards a peer or inspired to pursue a childhood dream after a conversation with your father. Exploring all these possibilities allows us to uncover potential not just within our relationships, but within ourselves and the world around us.

Fact. Adults long for secure attachments. 

Deep conversations will lead to secure attachments with one another. This translates to peace of mind for adults as they know someone will be consistently available, especially in times of changing physical or emotional needs. Such connections will strengthen your self-confidence while assuring you remain trusting and hopeful. 

Deep Questions To Get You Started

Getting to know someone deeply requires deep questions, not just sticking with the small talk. It also means that you need to be willing to share your answer to personal questions as well. We’ve gathered 20 of the best deep questions with further details surrounding why they will unlock emotional channels. These are open-ended probes which will facilitate long, in-depth discussions.

“The boldness of asking deep questions may require unforeseen flexibility if we are to accept the answers.”

– Brian Greene

Be prepared to go on a journey through the heart, soul, and mind. We’re going to help you to open doors and build relationships. Don’t rush into these. Many are powerful and demand respect.

1. What has been your biggest regret?

This question hits a sore spot, as thoughts of “What could have been,” resurface. Listen, don’t judge. This is a good time to remind one another of your achievements to date which may not have been, if things had panned out differently.

2. Are you happy?

This is a quick way to measure optimism. You’ll also learn what areas of life are yet to be fulfilled, and what milestones in life are valued most above all else.

3. Have you ever been in love?

Love can seem like a moving target. Whether you have hit it or not, it’s likely there has been some form of heartbreak in the past. Everyone has different experiences and different ideas which will always stay them. 

4. What was the saddest day of your life?

Nobody wants to talk about this one! If you’re working towards a lasting relationship, it will benefit to know this about each other as parts of the event could resurface anytime. When it does, you’ll react in a nurturing manner, providing comfort and being there when needed the most. Tip: Have tissues on hand for this one.

5. What do you think happens when we die?

Be prepared to debate with this one. If you do disagree, remember to consider one another’s feelings and the sensitivity of the topic before you react. 

6. What’s been the best moment in your life?

You might go back to childhood memories here if either one of you are sensitive. Other common moments are work achievements which highlights pride, or epic birthday celebrations which shows you practice gratitude. Unforgettable travel experiences are also raised here. Tip: Challenge yourselves to top it with each other!

7. What are you most proud of?

Cue work achievements. There are other things to consider here however. As life experiences vary, there are milestones such as parenthood and surviving health scares which can override career accomplishments. Before jumping in with a quick response, this is an opportunity to reflect on your choices and struggles, with persistence to stand tall with your head held high. 

8. What actions do you find unforgivable?

We’re all thinking it. Cheating. However, this conversation may surprise you as other behaviours are brought to the table. Childhood experiences as well as moral standing, results in unique values for every one of us. There’s no right or wrong response with this question. It’s all about learning what matters to one another.

9. What are you most passionate about?

There are so many topics to consider here! Family, traveling, health, career, love, wealth…..the list is endless. Once you know, you’ll both understand your reactions to various events. Moving forwards, you can be prepared to practice patience and console one another if anything relating to an identified passion were to become threatened.

10. What’s the most valuable thing you’ve ever learnt?

Life is a continuous learning experience, and it’s likely you’ve risen and fallen constantly learning from mistakes along on the way. Your most valuable lesson may come from experience, or could have been realised watching others, read in a book or seen in a film etc. Be prepared to inspire one another in this one!

11. What qualities do you look for in a partner?

Always an awkward one if the conversation is with a potential spouse! Nevertheless, one to be discussed. And if it’s another kind of relationship, you’ll always know what matters to each other, for your own practice as well as others you may introduce one another too. 

12. What makes you cry?

Emotional tears are triggered by rage, joy or sorrow. So which of these impacts you the most? Or perhaps you’re one of those people who just can’t cry.Tip: You might have to push through the proudness with this one if you’re a man or you’re speaking with one. Try discussing what makes you cry first…

13. When have you felt like a failure?

You’ll have to practice reassurance with this one as there are few emotions worse than feeling like a failure. And remember, we all have different values, passions and ambitions. What might seem like a trivial or insignificant hiccup to one person can actually feel like a major disaster to another. 

14. What is your most cherished childhood memory?

Childhood memories shape your life in the subtlest of ways. We specifically say ‘cherished’, to ensure this conversation will go back to a time when you were young and carefree. Warm and fuzzy feelings should emerge with this one. 

15. Where do you find meaning in your life?

Pride tends to dominate this question as others are inclined to raise the things they have achieved rather than those that mean the most. Take your time with this question. What events make you feel really really good?  Tip: The response should align with your passions. 

16. What’s your favourite place in the world?

Seems like a fun one right? London, Italy, Jamaica….Here’s the catch. Why is it your favourite place in the world? Holiday destinations say a lot about a person and highlight areas which need fulfillment. You could be after natural serenity, big city life, historical inspiration or ocean bliss. 

17. What is your biggest fear in life?

Fear will either show you your limitations or teach you about something you need to overcome. While only you can determine how you perceive your fear, one way to move past it is knowing that you’re not alone. Revealing it will remove a burden from your chest and probably diminish it over time as you become comfortable discussing it with the right people.

18. What three things would top your bucket list?

You can only pick three! This is an exciting question, as it comes with an increased possibility of achievement once revealed. You may share the same experiences and work together to knock every item off the list. Jumping out of a plane with someone else is always better than doing it alone!

19. What has been your biggest dream in life?

Dreams can come true. It’s never too late to chase something you’ve wanted your whole life. Discussing this with a friend could uncover the real reasons you’ve yet to accomplish your dreams. You may even discover it’s no longer what you want, or you’ve actually already achieved it. 

And last but not least…

20. If you died tomorrow, what would you wish you had done? 

Of course, any response is followed by ‘What are you waiting for?’ But really, what are you waiting for?

Time to get deep.

We’ve given you a long list of 20 of the deepest questions out there. Now, it’s up to you to make them blossom into fascinating, engaging conversations – ones you will never forget.

Remember, when someone opens up to you, it’s a privilege and a learning opportunity. 

“Learn from yesterday, live for today, hope for tomorrow. The important thing is not to stop questioning.”

– Albert Einstein

Be open-minded, empathetic, and understanding and expect the same in return. Be prepared to consider other perspectives, and don’t be afraid to shift your beliefs and views, even if they’re deep-rooted. 

Above all, listen. If you’re going to ask a deep question, it’s crucial that you give the other person plenty of breathing room to provide a well-thought-out answer.