Getting to know someone on a deeper level seems simple, but it’s all about asking the right questions.
We often stick to small talk and surface-level chat and end up missing out on the chance to truly understand what makes a person tick. By asking thought-provoking questions, you can dig a bit deeper and pinpoint what exactly makes someone who they are.
1. What’s the most important lesson you’ve learnt from a past mistake?
Source: Unsplash Our experiences shape the people we become, and there’s nothing more character-forming than our mistakes. Their response to this can give you some serious insight into who they are as a person.
2. If you could change one decision you’ve made, what would it be?
This taps into regrets and “what ifs” that linger in a person’s mind. It can shed some serious light on their values and priorities that might not be as evident on the surface. It also tells you whether they’re the type of person who finds it easy to move on or who clings to the past.
3. What’s a belief you hold that most people disagree with?
This question explores a person’s willingness to stand out from the crowd and their comfort with holding unpopular opinions. It can reveal independent thinking, creativity, or even contrarian tendencies.
4. How do you define success in life?
Everyone has their own measure of success, and this question gets to the heart of personal values and aspirations. Some might prioritise career achievements, while others focus on relationships or personal growth. Either way, their answer here will tell you what motivates them.
5. What’s the hardest thing you’ve ever had to forgive?
Forgiveness is complicated and really hard, and this question delves into a person’s capacity for empathy and healing. It can reveal how they handle betrayal, disappointment, and conflict resolution. It also lets you know if they’re someone who gives up at the first hurdle or whether they fight for relationships they truly care about.
6. What’s a fear you’ve overcome, and how did you do it?
This reveals how someone approaches challenges and their strategies for self-improvement. The response can tell you about their problem-solving skills, determination, and ability to push beyond comfort zones. It might also hint at past experiences that have shaped their current outlook.
7. What’s the biggest sacrifice you’ve made for someone else?
If you want to delve into a person’s capacity for selflessness and their priorities in relationships, this is a great question to ask. It can reveal the depth of their connections and what they value most in life. The answer can tell you a lot about their levels of empathy, loyalty, and the lengths they’re willing to go for those they care about.
8. How has your definition of love changed over time?
Our understanding of love often evolves with age and experience. This question explores personal growth and relationship history. It can reveal past heartbreaks, lessons learnt, and current expectations in romantic partnerships. It also reveals how emotionally mature and intelligent they are, which are good things to know!
9. What’s a personal belief you’ve completely changed your mind about?
The answer to this question reveals the person’s openness to new ideas and willingness to admit when they’re wrong. It can reveal intellectual curiosity and flexibility in thinking, too. Are they willing to grow, adapt, and reconsider their beliefs?
10. What’s the most valuable piece of advice you’ve ever received?
We all have at least one piece of wisdom that has had a lasting impact on our lives. Their answer here opens up about the influencers and mentors who have shaped the way they view the world.
11. How do you hope to be remembered after you’re gone?
This taps into a person’s legacy and what they consider most important in life. It can reveal their values, aspirations, and the impact they hope to have on the world. You’ll also get some insight into their sense of purpose, their relationships, and what they believe truly matters in the grand scheme of things.
12. What’s a personal flaw you’re working on improving?
Exploring self-awareness and the drive for personal growth is what you’ll be able to do with this question. It shows whether they’re capable of humility, introspection, and the ability to acknowledge where they might be falling short in life.
13. How has a failure or setback ultimately led to a positive outcome in your life?
This question delves into resilience and the ability to find silver linings in difficult situations. It can reveal optimism, adaptability, and problem-solving skills. You’ll also get to know whether they have good coping mechanisms and if they’re able to learn from their mistakes, which are very important things!
14. What’s a childhood dream you still haven’t given up on?
This question explores the connection between past aspirations and current goals. It can reveal perseverance, nostalgia, and the ability to stay hopeful even in the toughest times. The response will reveal a bit more about their passions, what they consider truly important, and how they balance pragmatism with idealism in pursuing their dreams.
15. How do you define happiness, and what makes you truly happy?
This gets to the core of personal fulfilment and contentment. It can reveal values, priorities, and what brings genuine joy to someone’s life. You can learn more about their emotional needs, life philosophy, and the relationships and experiences that matter most to them as well.
16. What’s a personal boundary you’ve had to set, and why was it necessary?
This one is all about self-respect and the ability to put themselves first when necessary. It can reveal past struggles, assertiveness, and emotional maturity. You don’t want to know that they’re a pushover or that they never consider anyone else’s needs. There has to be a balance.
17. How has your perspective on family changed as you’ve grown older?
This question delves into personal growth and evolving relationships. It can reveal shifts in priorities, understanding of generational differences, and appreciation for their bonds with their family members.
18. What’s a personal accomplishment you’re most proud of, and why?
If you want to know more about their self-esteem and what they consider truly valuable in their life, ask this. The answer will tell you a lot about their personal values, work ethic, and sources of motivation.
19. How do you cope with uncertainty and major life changes?
This question examines resilience and adaptability in the face of the unknown. It can reveal coping mechanisms, emotional regulation skills, and attitude towards change.
20. What’s a personal truth you’ve discovered that’s shaped your world-view?
Sometimes you want to go deep, and this question digs into the core beliefs that guide someone’s life. It can reveal profound realisations, philosophical leanings, and personal growth. The response might offer insights into their values, how they make sense of the world around them, and the experiences that have most significantly influenced their perspective on life.
