50 questions to get to know someone: build a deep connection

Why asking the right questions matters

Amidst such a busy pace of life, it’s far too easy to stay stuck in the superficial. Certainly, there’s a time and place for keeping things light and breezy. However, if we want to strengthen our relationships — whether it's at work or in our personal lives — it’s important to delve deeper.

When it comes to turning friendly acquaintances into lifelong friends or simply reinforcing our closest relationships, curiosity is key. Yes, to build rapport, it's important to open up to others and share information about ourselves.

But, what's even more crucial is to make them feel seen, heard, and understood by asking powerful questions.

In a research study on listening skills, the highest-quality listeners were those who mastered the art of asking relevant follow-up questions. Doing so opens up new pathways in conversation, which can be referenced in later exchanges to keep building the foundation of a stronger connection.

But how do you go about asking thoughtful questions that are appropriate to the situation? After all, the goal is to bring you closer together, not send them running for the hills!

Here are 50 powerful questions tailored to your level of familiarity.

Conversation starters for an authentic connection

So, you're in a scenario where you're meeting new people or becoming reacquainted with someone you haven't seen in a long time. Perhaps you're at a networking event or a wedding where you don't know anyone, or are catching up with old schoolmates at your high school reunion. Or, maybe you've just started at a new workplace, and are looking to build rapport with your colleagues quickly.

Research from Harvard shows that people love talking about themselves, because it fires up the motivation and reward circuitry in the brain.¹ So, by asking strangers and acquaintances plenty of questions about themselves, they'll likely leave the interaction feeling positive, and looking forward to your next chat.

In this situation, the goal is to go beyond small talk while still keeping things lighthearted and upbeat. Because, while nobody has learned anything about someone else by talking about the weather, it's best to ensure you're not prying into personal matters.

These fun questions will break the ice without feeling awkward.

2. What's the best trip you've ever been on, and why?
3. If you had to give a 5-minute presentation on any topic what would it be?
4. What's something that many people don't know about your background?
5. Which book had the most impact on you?
6. If you could live anywhere in the world, where would it be?
7. How would you spend your perfect day?
8. What did you want to be when you grew up?
9. What’s a personal project or goal you’re working towards right now?
10. What's something about you that would surprise others?
11. What's something you've changed your mind about recently?
12. If you had a time machine, what period in history would you travel back to?
13. What film can you easily watch over and over again?
14. What's something you're looking forward to right now?
15. What was your first job?
16. What's your favorite season?

Deeper questions to connect emotionally

Have you ever found yourself in a situation where you've met someone you 'vibe' with but aren't sure how to take the connection to the next level?

It might be a colleague you could see yourself being friends with outside work or a member of your partner's family. Often, building a more meaningful, lasting bond requires some vulnerability on each side. This means talking about topics that are a little more personal.

When asking deep questions, consent is key. The last thing you want is for the person to feel ambushed by personal questions. For example, you wouldn't ask someone immediately whether they plan on having children.

But, if you're already in a conversation about someone you know who recently gave birth and you want to segue into this topic, you might say: "Is it okay if I ask you a personal question?" and if they say yes, you might ask "Do you see children in your future?"

This can also work the other way by asking permission to lead the conversation.

When it comes to emotionally charged topics, Marlee's Founder and CEO, Michelle Duval suggests framing by saying something like: "Is it okay if I share some of my feelings about this topic with you?"

This technique is effective for inviting the person further into the conversation and helping them feel comfortable sharing.

Some thought-provoking questions you might ask to foster connection include:

16. What's the most challenging thing you've overcome in your life so far?
17. What's the best piece of advice you've ever received?
18. Have you ever had your heart broken?
19. What’s an ‘unpopular opinion’ you hold that not many would agree with?
20. What’s a trait you admire in others?
21. What’s the most adventurous thing you’ve ever done?
22. Who in your life has had the most impact on you?
23. What’s a cause you feel passionate about? What gets you fired up?
24. How do you want to be remembered?
25. Who did you admire when you were growing up?
26. What's your favorite childhood memory?
27. What's the scariest thing that's ever happened to you?
28. What's a risk you've taken that has paid off?
29. What's your earliest memory?
30. What's the most romantic thing you've ever done for someone?

Building intimacy: Questions for deeper romantic connections

When we're in a romantic relationship, it's easy to fall into the trap of thinking we already know everything about our partner. Sure, we may know their favorite genre of music, their pet peeves and how they plan to survive a zombie apocalypse.

But, humans are incredibly complex and multifaceted creatures. Even if you've been with your significant other for years, there are likely things that would surprise you about them (and vice versa).

To continue growing and evolving in your partnership, it's important to make an effort to keep peeling back the layers. Having these deep conversations regularly also keeps you on the same page, and may bring any unresolved issues to the surface.

Some insightful questions you might ask your romantic partner include:

32. What's a small thing I do for you that makes you feel loved?
33. Is there anything that I do that oversteps your personal boundaries?
34. What is your biggest dream for the future?
35. How do you want to be remembered?
36. What is your favorite memory in life so far?
37. What stands out as our most memorable moment together?
38. What's your biggest goal for us as a couple?
39. What's a family tradition you'd like us to continue together?
40. What would you like us to do more of together?

Past and future-focused questions for uncovering goals and values

There may also be times when you need to get to know someone quickly in a professional context. Maybe you're screening a candidate in a job interview, or need to figure out how to motivate an underperforming team member.

Or, perhaps you're a professional coach who needs to get to the root of a client's situation, so you can help them move forward.

Questions about the past are helpful for uncovering someone's core values and the habitual behaviors that influence their personality. Meanwhile, questions about the future illuminate their goals and what drives them at work.

Combining these questions will help you unearth what makes them tick. Some examples include:

41. What's your personal definition of success?
42. What's one piece of advice you would give to your past self?
43. What accomplishment are you most proud of?
44. What's one thing you thought you would never overcome but have?
45. What's been your most memorable day at work?
46. Who has inspired you the most throughout your career?
47. What would make this year a win for you?
48. What do you hope to do more of in the next five years?
49. What's a habit you want to start or stop doing?
50. What would you want your professional obituary to say?

The art of asking: Tips for meaningful conversations

Now you have a comprehensive list of questions you can pull from, no matter the occasion. But, the content of your questions is only one part of the occasion. What's equally important is how you ask.

When done effectively, asking questions is about co-creating with the person you're speaking to. You're inviting them into a collaboration, and it's important to be an active participant throughout the entire exchange.

Some practical ways you can do this include:

Tailor your approach

Everyone responds differently to questions, particularly when they're personal. Some people relish the opportunity to talk about themselves, while others don't and may be taken aback at first.

To ensure your question is well received, taking their communication style, personality, and motivations into consideration is key.

The good news is you don't have to rely on guesswork here. Our AI coach, Marlee, puts this information at your fingertips, telling you exactly how to connect with others.

Not only will you gain valuable insights about their communication preferences (for example, this person values non-verbal cues and the emotional tone of an interaction), but you can also pinpoint areas of similarity over which you can bond.

❤️ To get started, answer questions on what motivates you and invite your connections to do the same. Then, you can ask Marlee how to connect with each of them.

Ask Marlee, our AI coach, how to connect with someone

Balance open-ended and specific questions

To keep the conversation flowing and uncover new insights about the person you're talking to, it's helpful to use a mix of different question styles.

Specific questions with clear-cut answers can be great for warming up, and for gathering information you can reference later.

For example, "What was your favorite subject in school?"

Note that this isn't a question with a yes or no answer (which tends to lead to dead-ends in conversation), but it's nonetheless straightforward.

Meanwhile, open-ended questions are great for opening doors to new pathways in the conversation. They tend to elicit longer and more in-depth answers.

For example, the question "What is the biggest career setback you've experienced so far?" is likely to prompt your conversation partner to share a story in response.

Acknowledge their emotions

One of the biggest mistakes people make in conversations is jumping in with their own anecdote once the person has finished speaking. However well-intentioned this might be, it can come across as dismissive or invalidating.

If someone has just shared something personal, this can feel like a big deal to them. It's a good idea to take a beat to acknowledge and validate their emotions.

For example, you might say something like, "Thank you for sharing that with me, that must have been really difficult."

Research shows that creating this safe space for vulnerability releases oxytocin in the brain for both parties, which helps to create a trusting bond.²

Practice active listening

When it comes to having effective conversations, the in-between moments (where you're not speaking) matter. Research shows that 90% of interpersonal communication is non-verbal.³

It's important to pay attention to body language, including eye contact, posture, and hand gestures, as well as the tone and speed of their voice. This will help gauge their comfort in the conversation so you know when to ask probing questions and when to back off.

Equally, maintaining strong eye contact while they're speaking shows that they have your undivided attention. If it feels natural, you can also try to mirror their body language, which builds rapport between conversation partners.

Another way to show attentiveness is to use verbal minimal encouragers like "Mmm", "Sure", "Yes" or gestures like nodding and facial expressions to encourage them to continue. However, don't go overboard, as it can feel like you're interrupting.

Another great way to be an effective listener is to use relevant follow-up questions. For example, if they've told you about the biggest obstacles in their career, you might ask them what advice they would give someone else in that situation.

Summarization is another valuable strategy, as it allows you to confirm your understanding and helps the person feel heard.

Together, these skills are known as active listening. Research shows that this skill is considered the most valuable leadership competency by 64% of HR professionals⁴ and is crucial in all areas of life.

Get to know yourself and others through meaningful questions

When it comes to finding common ground with the people around us, questions are perhaps our most valuable tool.

They help us nurture more rewarding relationships, as well as unearth surprising new insights about ourselves.

By acting as a guide, sounding board and coach, AI Coach Marlee facilitates these connections. You can ask Marlee any question about yourself or others and receive insightful responses backed by powerful people analytics.

Plus, receive tailored coaching in areas like emotional intelligence to help you become a more authentic and masterful communicator.

Get started with Marlee today.