Meeting new people can be exciting and enriching, offering the chance to explore new perspectives and build meaningful connections. However, transitioning from surface-level small talk to deeper conversations can often be challenging. Forming a genuine connection involves more than just sharing favourite hobbies or foods; it’s about uncovering what truly makes someone tick, what brings them joy, and how they navigate life’s challenges. 

One effective way to move past the initial formality and dive into a deeper friendship is by asking thoughtful questions and genuinely listening to the responses. These questions are designed to reach a person’s core, revealing their passions, values, and experiences. By engaging in these deeper conversations, you can make your interactions smoother and more meaningful, paving the way for lasting relationships.

20 Questions

1. What’s your favourite way to spend a day off?

This question opens up a window into their interests and passions. It reveals how they like to relax and what activities they enjoy most. 

2. What’s one of the most memorable experiences you’ve had?

By asking this, you can uncover significant events that have shaped their life and what they hold dear in their memories. 

3. If you could learn a new skill instantly, what would it be?

This question can reveal aspirations and interests they might not have the time or opportunity to pursue. 

4. What challenges have you faced recently, and how did you overcome them?

Understanding someone’s recent challenges and their approach to overcoming them provides insight into their resilience and problem-solving skills. 

5. Who has had the most significant impact on your life?

This can help you understand their influences and the values they hold due to these relationships. 

6. What’s your favourite book or movie, and why?

Learning about their favourite book or movies can provide insight into their tastes, values, and what stories resonate with them. 

7. where would you go and why if you could travel anywhere?

Travel dreams can reveal a lot about their sense of adventure, curiosity, and what cultures or experiences they value. 

8. What’s something you’re passionate about that might surprise people?

This question can uncover hidden talents or interests that aren’t immediately obvious. 

9. How do you handle stress and pressure?

Understanding how someone manages stress can give you a glimpse into their coping mechanisms and mental health practices. 

10. What’s one goal you’re working towards right now?

This can reveal their ambitions and what they strive to achieve in their personal or professional lives. 

11. What’s the best piece of advice you’ve ever received?

Hearing the advice that has resonated most with them can offer insight into their values and guiding principles. 

12. What do you value most in a friendship?

This can help you understand what they prioritise in their relationships and what kind of friend they aspire to be. 

13. What’s one thing you’ve always wanted to try but haven’t yet?

This question can bring out their adventurous side and any latent dreams or goals they have. 

14. How do you define success?

Understanding their definition of success can reveal their values and what they strive for in life. 

15. What’s your favourite memory from childhood?

Childhood memories often hold a special place in our hearts, and sharing them can bring out fond reflections and deep connections. 

16. What’s a topic you could talk about for hours?

This can help you discover their passions and interests that deeply engage them. 

17. How do you like to spend your time when you’re alone?

Knowing how they enjoy solitude can give you insight into their self-care practices and interests. 

18. What’s a belief or opinion you hold that’s changed over time?

This can provide a window into their personal growth and how their perspectives have evolved. 

19. What’s the most spontaneous thing you’ve ever done?

Spontaneity can reveal their adventurous side and how they approach life’s unexpected moments. 

20. What are you most grateful for in your life right now?

Gratitude is a powerful emotion; understanding what someone is grateful for can show you what they truly value and cherish.

You can move beyond the surface and build a meaningful connection with someone new by asking these questions and actively listening to the answers. Each response opens a path to deeper understanding and shared experiences, making your interactions richer and more rewarding. So, next time you meet someone new, try out a few of these questions and see where the conversation takes you.