Some conversations just skim the surface—easy, casual, polite—and that’s fine when you’re making small talk.
However, if you’re craving something real, if you want to actually feel connected to the person sitting across from you, then you need to ask questions that invite more. The right question can open up laughter, memory, grief, self-reflection, or even joy. Whether you’re with a partner, a friend, or someone new, here are some things to ask that tend to unlock more than just words. They build bridges, and they make space for meaning—and isn’t that what it’s really all about?
1. “What’s something you’ve changed your mind about in the past year?”
People evolve, but we don’t always get a chance to talk about how, or why. This question encourages thoughtfulness without asking anyone to be overly vulnerable right away. It’s a window into their inner growth, the moments that made them pause, and the thoughts that shifted along the way.
It also keeps the conversation grounded in the present. You’re not asking about a dramatic life overhaul. You’re just asking: where has your thinking softened, stretched, or surprised you recently?
2. “What kind of connection are you craving most these days?”
This isn’t your typical “how are you?” It taps into the quieter parts of someone’s emotional life—what they’re missing, hoping for, or slowly realising they need more of. Connection looks different for everyone, and this question respects that without assuming anything.
It’s a great way to understand someone’s current emotional landscape. Their answer might be romantic, platonic, creative, or even spiritual, but either way, it’s a clue about what’s really going on beneath the surface.
3. “What’s something you wish more people understood about you?”
This question makes space for someone to name the part of themselves that often feels overlooked or misunderstood. And it does so without turning the moment into a therapy session—it simply asks, “What do you wish other people could see more clearly?” It invites a kind of honesty that can be surprising in how quickly it deepens the conversation. You might learn what frustrates them, what they’ve outgrown, or even what they’re quietly proud of.
4. “What part of your life feels the most meaningful right now?”
This is the kind of question that cuts through small talk and goes straight to the heart. You’re not asking what they’re doing—you’re asking what’s resonating. What’s grounding them. What’s giving them a sense of purpose lately, even if it’s small or understated. It also encourages people to reflect on where they’re investing their energy, and whether that part of life is feeling rich, heavy, exciting, or all three. The answer often reveals what they value most, right now.
5. “Is there a belief you grew up with that you’ve outgrown?”
This question isn’t about rebellion; it’s about growth. We all inherit beliefs from family, school, culture, or faith communities. However, sometimes, the most powerful turning points in life come when we realise something no longer fits who we’re becoming. This opens the door to big changes and quiet awakenings. It allows someone to trace their evolution, and it often leads to surprising stories about where they’ve been and how they got here.
6. “What’s something you’re proud of that no one really sees?”
We live in a world where only the loudest wins get celebrated. This question flips that completely. It invites someone to share a quiet victory, a piece of personal growth, or even a small habit that means the world to them, whether or not anyone claps for it. It’s a beautiful way to see someone more clearly. When people talk about what matters to them, not just what looks impressive on the outside, you learn a lot about their values and inner life.
7. “When do you feel most like yourself?”
This one cuts right to the core. It bypasses roles, achievements, and expectations, and goes straight to authenticity. Everyone has moments where they feel most at ease, most alive, most real—this question helps them name that. Plus, it often reveals more than you’d expect. Sometimes it’s in movement. Sometimes it’s in silence. Sometimes it’s around certain people. Whatever the answer, it tells you where their soul feels safe.
8. “What are you currently unlearning?”
Unlearning isn’t talked about as much as learning, but it’s often where the deepest change happens. This question gives someone space to name the things they’re letting go of—habits, ideas, fears, or identities that no longer fit. It’s a generous, open-ended question that invites honesty, even if someone’s still figuring it out. You don’t have to have it all worked out to reflect on what’s shifting underneath.
9. “What’s bringing you joy in a small, quiet way right now?”
Source: Unsplash We’re wired to notice big moments, but joy often sneaks in through the smallest cracks. This question flips the focus to what’s nourishing, even if it’s simple—like warm light in the morning, a new playlist, or five uninterrupted minutes with a cup of tea. It creates space for gratitude, play, and presence. Sometimes, hearing someone name those joys reminds you to notice your own.
10. “Who’s someone who’s had a lasting impact on you, and do they know it?”
This one is all about appreciation, and often, emotion. We all have people who shaped us—sometimes gently, sometimes profoundly, but we don’t always get the chance to talk about them, or acknowledge them out loud. Asking this often leads to stories about mentors, friends, grandparents, or even brief encounters that changed everything. It usually makes the person want to reach out and say something that’s been sitting unsaid for too long.
11. “What are you currently learning to accept?”
Source: Unsplash Acceptance can be one of the hardest emotional skills to build. This question offers room for someone to be honest about what they’re learning to live with—whether it’s a personality trait, a life circumstance, a disappointment, or even a loss. It’s not about forcing positivity; it’s about recognising the stretch between resistance and peace. This one often leads to grounded, vulnerable, quietly powerful conversation.
12. “What do you want more of in your life, and what’s getting in the way?”
Source: Unsplash This is a clarity question. It asks someone to name what they’re hungry for, and to consider what’s blocking the way, without turning it into a productivity checklist or a guilt spiral. Sometimes the answers are practical. Sometimes they’re emotional. But either way, it gives someone permission to name their longing and reflect on their stuck points with honesty and self-compassion.
13. “What story do you rarely tell but probably should?”
Source: Unsplash Everyone carries stories they rarely share. Maybe they feel too personal, too strange, or too overlooked. This question gently invites someone to open up something that’s been sitting in their chest, waiting for a safe place to land. You don’t have to push. Just listen. When people share these stories, they often feel lighter, and more deeply seen.
14. “If your younger self could see you now, what would they be proud of?”
Source: Unsplash We spend a lot of time thinking about where we’re falling short. This question flips that. It invites warmth, perspective, and reflection on how far someone’s already come, even if they don’t give themselves credit very often. It also invites a kind of kindness toward the present version of yourself. Because chances are, you’re doing better than you realise.
15. “What question do you wish people asked you more often?”
Source: Unsplash This is the one that opens the door wide. You’re offering someone full control of the conversation, and showing them that you genuinely want to connect on their terms, not just your own. People often pause when they hear this one. However, their answer can take the conversation in a direction you never expected, and sometimes, that’s where the most meaningful moments live.
