If you want to truly connect with someone, you’ve got to dive deep.
However, asking the standard questions about their childhood or their goals in life will only get you so far. You’ll need to have some more questions up your sleeve to really get to know who they are and bond with them. Here are some unique questions you can ask that should shine a whole new light on the person they are deep down.
1. “What’s something you’ve always wanted to do but never had the chance to?”
This question opens the door to dreams, ambitions, and maybe even a little nostalgia. It gives you insight into what excites them and what might still be on their bucket list. Plus, it can lead to a fun discussion about ways they might still make it happen.
2. “What’s a memory that still makes you laugh out loud?”
Laughter is a fantastic way to connect, and this question taps into their happiest, funniest moments. Sharing a story that makes them laugh again helps lighten the mood and creates a positive vibe between you. You might even find a shared sense of humour along the way.
3. “If you could live anywhere in the world, where would it be and why?”
Dreaming about places to live reveals a lot about someone’s personality and values—do they prefer city excitement, beach relaxation, or countryside charm? This question can also spark conversations about travel, lifestyle preferences, and personal goals.
4. “What’s a skill or hobby you’ve always admired in other people?”
This lets you explore their interests and even their secret aspirations. Maybe they’ve always wanted to play an instrument, paint, or learn a language. Talking about it might even inspire them to pursue it—and you might discover a shared interest to explore together.
5. “Who’s had the biggest impact on your life?”
This question dives into their personal history and the people who shaped them. Whether it’s a parent, mentor, or friend, hearing about these relationships gives you a deeper understanding of their values and what’s important to them.
6. “What’s the best piece of advice you’ve ever received?”
Sharing meaningful advice helps you understand their perspective and invites you to learn from their experiences. It’s a window into their outlook on life and the wisdom they’ve picked up along the way.
7. “What’s your go-to comfort food and why?”
Food has a way of bringing people together, and this question taps into their personal tastes and memories. Maybe it’s something their gran used to make or a guilty pleasure they can’t resist. It’s a simple question, but it often leads to warm, nostalgic conversations.
8. “What’s a challenge you overcame that you’re really proud of?”
Talking about their triumphs gives them a chance to reflect on their resilience and share a piece of their journey. It also gives you insight into their strengths and what drives them. These stories often reveal more about a person than any other question.
9. “If you could relive one day of your life, what would it be?”
This question lets them revisit a moment that holds special meaning. Whether it’s a day filled with joy, achievement, or love, it gives you a glimpse into what truly matters to them. It also creates space for a heartfelt and reflective conversation.
10. “What’s something small that brings you a lot of joy?”
Sometimes, it’s the little things that mean the most. Whether it’s their morning coffee, a favourite song, or a sunny day, this question focuses on life’s simple pleasures. It’s a great way to share smiles and find common ground.
11. “What’s a lesson you wish you’d learned sooner?”
Source: Unsplash Everyone has moments of hindsight, and this question opens the door to sharing personal growth. It’s a way to talk about what they’ve learned from life without dwelling on regrets, keeping the conversation thoughtful but uplifting.
12. “What’s something you do that always surprises people?”
Source: Unsplash This playful question invites them to share something unexpected about themselves, from hidden talents to quirky habits. It’s a fun way to dig deeper and uncover layers of their personality that don’t always show up in everyday conversations.
13. “What’s your ideal way to spend a lazy weekend?”
Source: Unsplash How someone spends their downtime says a lot about who they are. Whether they prefer binging a series, hiking, or trying new recipes, this question helps you understand what relaxes and recharges them. It’s also a great way to suggest shared activities.
14. “What’s something you wish people understood about you?”
Source: Unsplash This question creates a safe space for them to share their thoughts, feelings, or struggles that might not come up otherwise. It can lead to deeper empathy and a stronger bond, showing them that you’re genuinely interested in their perspective.
15. “What’s your favourite thing about yourself?”
Source: Unsplash Encouraging someone to reflect on their own strengths and self-love is both empowering and heartwarming. It’s a positive way to end a meaningful conversation and helps them see themselves through a more confident lens.
