10 thoughtful questions for getting to know someone
When the goal is to get to know the person sitting across from you on a deeper level, the trick is to skip the flim-flam — the job, the postcode, the weekend — and ask the questions that lead to real answers. Below are ten of them. Each one is short. Each one is openable. And each one tells you something useful if you actually listen to the answer.
These work best when you’ve got more than five minutes — a virtual speed dating round with longer slots, the end-of-night chat at the bar, or a second date. If you’re looking for a wider, lighter list to use round-by-round on the night itself, see 40 great speed dating questions to ask. And if it’s your first event, What to expect at a speed dating event covers the basics first.
A note before you start#
The goal of these questions is not to interrogate but to foster genuine, meaningful conversations. Pick two or three. Ask, listen, share something of your own, then ask “really? why?” The follow-up question is where the connection lives.
1. What are your hobbies and passions?#
This invites your date to share what they’re genuinely enthusiastic about. Their hobbies often reflect their interests and what brings them joy, providing insights into their personality.
Listen for: whether they light up when they talk about it. The thing they’re passionate about matters less than how they sound describing it. Follow up with: “How did you get into that?” or “What’s the bit other people don’t realize about it?“
2. Can you describe your perfect day?#
Asking about their ideal day allows your date to paint a picture of their preferences and values. It can reveal whether they’re introverted or extroverted, adventurous or laid-back.
Listen for: who else is in the day. A perfect day spent alone, with a partner, with a crowd, or with family tells you a lot about how they like to live. Follow up with: “When did you last actually have a day like that?“
3. What’s your most cherished childhood memory?#
Childhood memories are windows into a person’s formative years. Learning about their favorite experiences can provide a glimpse into their upbringing and early influences.
Listen for: whether it’s a place, a person, or an event. People remember different things for different reasons. Follow up with: “Does any of that still show up in how you spend your time now?“
4. What makes you laugh?#
Laughter is a universal language, and understanding what tickles your date’s funny bone can give you a sense of their sense of humor and what brings them joy.
Listen for: the difference between a comfortable answer (“dry humor, sitcoms”) and a specific one (“the way my dad mispronounces names”). The specific one is the real one. Follow up with: “When did you last properly laugh — like couldn’t-stop laugh?“
5. If you could travel anywhere in the world right now, where would you go?#
Travel destinations often reflect our aspirations, interests, and dreams. This question can uncover your date’s sense of adventure and their cultural interests.
Listen for: whether they pick a city, a landscape, or a culture. Each maps to a very different kind of curiosity. Follow up with: “What’s stopping you?” — which is sometimes the most interesting bit of the whole answer.
6. How do you handle stress or challenges?#
Their approach to stress and challenges can reveal aspects of their personality, such as resilience, problem-solving skills, and whether they tend to remain calm or become anxious.
Listen for: self-awareness. A confident “I go for a walk and ring my sister” is more reassuring than a polished “I stay completely calm under pressure”. Follow up with: “What’s a recent example?“
7. What kind of books, films or art do you enjoy, and why?#
Asking about their artistic and cultural preferences can offer insights into their tastes, values, and the emotions they connect with.
Listen for: whether they answer with titles or with feelings. Both are good — but a person who says “anything that makes me cry on a train” is telling you a different thing to one who lists three directors. Follow up with: “What’s the last one that genuinely moved you?“
8. Tell me about a significant life lesson you’ve learned.#
This question delves into your date’s experiences and personal growth. It can highlight their wisdom, maturity, and capacity for self-reflection.
Listen for: whether they own the lesson. “I learned not to trust people” is a flag; “I learned I’m too quick to say yes” is self-reflection. Follow up with: “What did you do differently after that?“
9. What are your core values and beliefs?#
Understanding your date’s values and beliefs is essential for compatibility. This question can reveal their moral compass and principles that guide their decisions.
Listen for: one or two specific values, not a generic list. “Loyalty and curiosity” beats “honesty, kindness, hard work” every time. Follow up with: “When have you had to actually live by that?“
10. What are your long-term goals and dreams?#
Knowing your date’s aspirations can give you a sense of their ambition and what they envision for their future. It also allows you to see if your goals align.
Listen for: the timescale. Some people think in years, some in decades, some in next-week. Follow up with: “And what’s the smallest thing you’re doing about that right now?”
One last thing#
The best way to get to know someone’s personality is through open and honest communication. Listen attentively, share your own experiences and thoughts as well, and let the conversation drift where it wants to go. Relax, be yourself, and enjoy the journey of discovering the fascinating layers of the person you’re with.
When the event is over, head back to Fanciful and log your picks against your scorecard — see What to expect at a speed dating event.