How to ask more meaningful questions and embrace deeper connections

Bored of the same old small talk? Spark meaningful conversations and build deeper relationships with these expert tips and question prompts. 

In our bustling, digitally-driven world, where social media platforms clamour for our attention and our lives seem to move at the speed of light, it's easy to feel disconnected. Amidst the constant scroll and swipe, are we truly fostering meaningful relationships, or are we merely skimming the surface of human connection? 


Though our devices undoubtedly bring huge conveniences – we can order groceries, book appointments and message friends on the opposite side of the world, all with a few quick taps. There are the inevitable downsides, too. Attention spans are getting shorter, studies have found that loneliness is on the rise, and it raises questions about the depth and quality of our relationships with those around us. 


“As humans we are social creatures, therefore social connection is important for our wellbeing and mental health,” says Jade Thomas, psychologist and founder of Luxe Psychology Practice. “Creating and maintaining good connections with others can also help to combat loneliness and improve mental health issues, such as stress and anxiety.” 


The route to creating those good connections and, more importantly, maintaining them could lie in our ability to navigate deep and meaningful conversations. Pushing beyond surface-level small talk and creating openness and intimacy in our interactions with each other. 


“Thoughtful questions are the scaffolding of any meaningful conversation,” says Thomas. “We can improve our conversations by asking open-ended questions, posing one question at a time, becoming comfortable with silence and thinking of conversations like a game of tennis – each individual having equal opportunity to participate in the conversation.” 


Ready to go deeper? Try these expert tips and question prompts to spark deeper and more meaningful connections. 



Before you dive into asking deeper questions of others, it’s important to do some self-reflection, says Lorena Bernal, life coach and founder of Live Love Better. After all, what’s a meaningful conversation if you can’t participate as your full and authentic self? 


“We are more connected than ever, yet we feel more alone than ever because what we share with others veils our truths, leaving our authentic selves unseen and unheard,” says Bernal. “The journey towards cultivating deeper connections begins with introspection. By engaging in self-reflection and asking ourselves profound questions, we embark on a process of self-discovery that’s both revealing and transformative.” 


Bernal suggests asking yourself these three questions to help lay the foundation for authentic interactions. They’re also great prompts for mindful journaling 


  1. What brings me joy? 
  2. What are my deepest fears? 
  3. How do I want to be remembered?


Read: Try these 10 easy ways to feel more joy 




Whether it’s those we work with or our friends and partners, slipping into mundane everyday conversations can be all too easy. Even well-meaning questions such as ‘how was your day?’ can feel routine and prompt auto-pilot answers. This is where having a few considered prompts can come in handy to spark conversations that feel refreshing and authentic. 


“Each interaction presents a unique opportunity to forge a deeper connection through thoughtful, empathetic dialogue,” says Bernal. “Conversation starters and question prompts play a crucial role in this endeavour, serving as gateways to richer, more engaging exchanges.”  


When the moment feels right, try some of Bernal’s go-to question prompts. 


Ask your colleagues… 

  • Why do you do what you do? 
  • Is this job fulfilling your dreams? 


Ask your partner… 

  • Who are you at your core, beyond societal labels? 
  • Do you feel loved? 


Ask your kids… 

  • What activities make you lose track of time? 
  • What is your favourite thing I do for you? 


Ask your parents… 

  • Who were you before having children? 
  • What were your dreams? 


Ask your siblings… 

  • What is your perspective of our childhood story? 
  • Do you see mum and dad and how they raised us the same way I see it? 


Ask a stranger… 

  • What's your story? 
  • What experiences have shaped you? 



Diving into new deep and meaningful conversations can feel intimidating, especially if you’re attempting to change a dynamic with others who may be comfortable with their status quo. There’s also potential for things to get somewhat awkward if your profound conversation starter is a bit of a non-starter.  


But fear not, Bernal has you covered with these tips for embracing deeper exchanges and making space for others to feel comfortable in following your lead. Hopefully, it’ll help you push past any awkward moments too. 


1. Be prepared to be vulnerable

“When asked a superficial question, responding with a thoughtful, profound answer can shift the dynamic of the interaction, demonstrating the value and richness of a more meaningful exchange,” says Bernal. “This approach not only enriches our personal connections but also serves as a subtle invitation for others to engage more deeply, creating a ripple effect that can transform the nature of conversations within our communities.” 


2. Reframe discomfort as a path to connection

“Initial discomfort often stems from unfamiliarity rather than an inherent awkwardness in seeking depth,” notes Bernal. “Like any skill, the art of deep conversation becomes more comfortable and natural with time and repetition.” 


3. Honour your need for deeper connections

For Bernal, recognising and honouring your need for deeper connections is crucial: “If you feel a genuine desire to forge more meaningful relationships, it's important to pursue this instinct. The individuals who are meant to connect with you on a deeper level will welcome your efforts and reciprocate.” 


4. Use awkwardness as a filter

“The varied reactions you receive when attempting to engage in deeper conversations can act as a filter, helping you discern who you want in your life,” suggests Bernal. “Though it's important to remember that we all have different preferences for interaction, and not everyone will resonate with the desire for deeper engagement. And that's perfectly okay.” 


5. Inspire others through your courage

“By taking the initiative to ask profound questions and seek deeper connections, you also serve as an inspiration to others,” says Bernal. “Many people yearn for more meaningful interactions but hold back due to fear of awkwardness or rejection. Your courage to break through these barriers not only enriches your own social experiences, but also encourages others to explore beyond the surface in their relationships.” 


6. Take the leap without judgement

“To truly overcome the awkwardness associated with deep conversations, it's essential to take the leap without overthinking or fearing judgement,” Bernal advises. “Remember, the worst-case scenario is that someone might not resonate with your approach, but even this outcome has a silver lining – it helps reveal those who genuinely align with your authentic self.” 


For more tips on how to live a more authentic life, discover our authenticity masterclass