Explore personal questions to help you get to know someone and deepen your connection. Plus, learn how questions can be a tool to beat social anxiety.

Meeting new people can be exciting and opens up a world of deep conversation and shared experiences. But when it comes to forming a new connection, it can be tricky to move beyond the small talk to actually get to know someone.

One way to move past formality and dive deeper into friendship is by asking the right questions and taking time to listen to the response. It isn’t just about finding common hobbies or favorite foods — it’s about reaching the core of a person and discovering what makes them tick, what brings them joy, or how they’ve overcome challenges.

We’ll guide you through the kinds of questions that can help you get to know someone on a deeper level and make your interactions smoother and more meaningful.

How questions help ease social anxiety (as well as deepen connection) — and how to use them

Engaging with new people can sometimes stir up social anxiety. Having a set of questions handy when you walk into an event or first interaction with someone can feel empowering and ultimately help ease your discomfort.

Here are 11 tips for using questions to create a comfortable space for dialogue in anxiety inducing situations.

1. Prepare your questions

Have a list of questions in mind before heading into social settings. You don’t need many. Even a few questions can lead to long, enjoyable conversations.

2. Practice active listening

When you ask a question, listen to the answer with genuine interest. Active listening shows you care and want to understand the other person.

3. Show curiosity

If something sparks your interest during the conversation, ask more about it. Showing curiosity will not only help you learn more but also make the other person feel valued.

4. Stay open-minded

People may have different experiences and viewpoints. Keep an open mind when listening to their responses, and you may discover something new and intriguing.

5. Practice regularly

The more you practice asking questions and engaging in conversations, the more comfortable you’ll become. Over time, this practice can help reduce social anxiety.

6. Encourage reciprocity

Invite the other person to ask you questions, too. Engaging in a mutual exchange of ideas and experiences can be very enriching.

7. Try to focus on the positive

Maintain a positive attitude, and remember: every conversation is an opportunity to learn and grow.

8. Engage in self-reflection

Reflect on the conversations you have. What did you learn? How did it feel? Self-reflection can be a great way to work through social anxiety and improve your communication skills.

💙 Ease your anxiety Before a Social Engagement with this meditation from the Confidence series on Calm.

30 essential questions to ask to get to know someone more deeply

To help you deepen your new relationship, try asking questions that are designed to help you understand the other person's background, interests, and values.

10 essential questions to ask to get to know someone

Start with questions to help you discover the essence of the person. As you talk, you can gradually deepen the conversation, paving the way to more personal and profound topics.

1. What childhood memory makes you smile?

2. What drives you to get up every morning?

3. How do you spend your free time?

4. What are your hobbies and how did you get into them?

5. What goal are you working toward right now?

6. What subjects, current events, or causes are you passionate about?

7. What’s your favorite way to unwind after a hectic day?

8. If you could visit any place in the world, where would it be and why?

9. What book or movie left a lasting impression on you?

10. Who do you look up to, and why?

💙 Practice the art of mindful Listening in our Relationship with Others series to help you fully receive the answers someone is giving you.

10 personal questions to ask to better understand someone

After warming up with the essential questions above, you may feel ready to explore the more personal questions below, which can bring a new layer of understanding and empathy into your conversations. These questions aim to encourage others to share intimate experiences and emotions that can help to create a foundation for meaningful and lasting relationships.

1. What’s an experience that significantly shaped who you are today?

2. Who’s been the most influential person in your life?

3. How do you navigate through difficult situations or conflicts?

4. What fear have you overcome, or are you working to overcome?

5. What insecurities, if any, are you willing to share?

6. Tell me a cherished achievement, and what did it mean to you?

7. How do you handle criticism, and do you use it for personal growth?

8. What values are fundamental to you and why?

9. What’s your definition of a fulfilling life?

10. Is there a particular philosophy or mantra that guides your life decisions?

💙 Explore using mindful listening and thoughtful questions to facilitate Deeper Communication in the Daily Jay.

10 questions to ask to know someone on the deepest level

As your conversations progress, there may be an opportunity to venture into more profound topics. The questions below are designed to evoke thoughtful responses and encourage introspective dialogue.

They can be enlightening, helping both you and the person you're engaging with to explore life's broader themes together. They’re not just questions to ask to get to know someone — they’re prompts to explore the human experience.

1. What does happiness mean to you, and how do you pursue it?

2. How do you define success in life?

3. What core values guide your actions and decisions?

4. Do you have a personal philosophy that shapes your outlook on life?

5. What do you think the purpose of life is?

6. How important is family to you?

7. What steps do you take for personal growth and self-improvement?

8. How do you handle life’s uncertainties and challenges?

9. What important lessons has life taught you?

10. How do you look after yourself when you face adversities?

💙 Explore the importance of Real Connection in our relationships during the Daily Calm.

Questions to ask to get to know someone FAQs

Q: What are 20 questions to ask to get to know someone?

Getting to know someone can be an exciting journey. Try these 20 questions to spark meaningful conversations to help you get to know someone in a fun and friendly way.

1. What’s your favorite way to spend a weekend?

2. Do you enjoy what you do for a living?

3. What’s a book that you’d recommend?

4. Are you a morning person or a night owl?

5. What’s your dream job?

6. Do you have any pets?

7. What’s your favorite type of cuisine?

8. Do you have any siblings?

9. What kind of music do you enjoy?

10. Where have you always wanted to travel to?

11. How do you stay active and healthy?

12. What’s a skill you’re proud of?

13. Do you enjoy spending time outdoors?

14. What’s your idea of a perfect vacation?

15. Do you have any favorite TV shows or movies?

16. What do you wish you had more time to do?

17. What’s a cause you feel strongly about?

18. How do you like to stay updated on current events?

19. Is there a hobby you’ve always wanted to try?

20. What’s something you love learning about?

Q: What's a deep question to ask someone?

A deep question is one that invites people to share their core values and what truly matters to them. An example of a deep question could be: “What do you think is the most important thing in life, and why?”

Q: What are 5 powerful questions?

Five powerful questions that can evoke reflection and meaningful discussions are:

1. What drives you to do what you do?

2. When you’re faced with challenges, how do you overcome them?

3. Is there a moment in life that transformed you?

4. What do you believe in that others might not?

5. What does fulfillment mean to you?

These questions challenge people to delve into their motivations, experiences, and beliefs to foster a more meaningful conversation.

Q: What to ask someone you like?

When you like someone, you might want to know more about their life and interests. Here are a few questions to ask someone your interested in:

• What activities do you enjoy during your free time?

• Are there any books, movies, or music you've been into lately?

• Do you enjoy traveling? If so, what’s been your favorite place so far?

• What’s your idea of a great weekend?

• How do you feel about adventures or trying new things?

These questions are light, fun, and open-ended, which can help make the conversation enjoyable and natural.

Calm your mind. Change your life.

Mental health is hard. Getting support doesn't have to be. The Calm app puts the tools to feel better in your back pocket, with personalized content to manage stress and anxiety, get better sleep, and feel more present in your life.