60 Questions to Ask to Get to Know Someone Better (2024)

Building and maintaining healthy connections with others is one of the most fulfilling parts of life.

No matter your personality type or extroversion level, cultivating meaningful relationships is essential for feeling a sense of belonging and purpose. And because much of our time is spent in the workplace, this extends to fostering positive relationships with colleagues.

Sometimes, building new relationships can feel intimidating — breaking the ice isn’t always easy. To make this task less daunting, equip yourself with a collection of thoughtful questions to ask to get to know someone.

Instead of wading in the waters of small talk, build deeper connections and leave a striking first impression. Here are 60 questions for getting to know the people around you.

Why you should ask getting-to-know-you questions

Posing thoughtful questions shows that you’re personable and approachable. It also communicates to others that you value their individuality and want to get to know them better. A great query reflects your curiosity and ability to listen and learn, setting you apart as an engaging and exciting connection.

Although asking questions is a great way to build your communication skills and confidence, it doesn’t come naturally to everyone.

During a conversation, it’s easy to become nervous and defect to talking about yourself. It comes naturally: studies have shown that humans devote 30–40% of everyday speech to informing others about their own experiences.

But taking the time to get to know other people is a worthwhile endeavor for your personal development. And asking questions can even make others like you more.

Benefits of having deeper conversations in the workplace

Unlike friends, you don’t choose who you work with. Often, this is a great thing: you have the opportunity to connect with people you may not have met otherwise. However, that can make finding common ground for non-work-related chit-chat a bit difficult. With conversation starters to fall back on, you can avoid awkward lulls and stretches of silence.

Increased empathy

Deep conversations allow individuals to share their personal experiences and feelings. This sharing can help colleagues better understand each other's emotional states and backgrounds. This fosters empathy, making team members more accommodating and supportive of each other's needs.

Enhanced team cohesion

Team members can develop stronger bonds by discussing topics beyond day-to-day tasks. This enhanced sense of unity and belonging can lead to more effective collaboration and a more cohesive team environment.

Better understanding of diverse perspectives

Diverse conversations broaden understanding and appreciation for different cultures within a team. This can lead to more innovative problem-solving and decision-making as different perspectives are considered and voices are heard.

Improved conflict resolution

Teams accustomed to deep conversations are often better equipped to handle conflicts. Open communication helps prevent misunderstandings and allows for resolving disagreements constructively before they escalate.

Increased job satisfaction and morale

When employees feel heard and understood, their job satisfaction typically increases. Deep conversations can contribute to a more positive workplace atmosphere, reducing turnover and boosting morale.

Why is it difficult to ask get-to-know-you questions?

It’s easy to overthink your interactions when meeting new people. Perhaps you’re worried about how others will perceive you or that you may leave a negative impression. Social anxiety may even encourage you to believe making no impression at all is the safest approach.

Although the benefits of social connections are widely accepted, perceived risks build barriers for many people to pursue them.

According to a study from the Journal of Experimental Social Psychology, people tend to be pessimistic about how strangers will perceive them. They may worry that these people will reject them or be uninterested in what they have to say.

While these feelings are normal, they can hinder your ability to connect with others because they can stop you from starting conversations in the first place.

But the same study revealed that, although talking to strangers can be intimidating, it’s possible to learn to adopt an optimistic attitude. After completing tasks that involved interacting with strangers, the participants felt more comfortable and confident, and their expectations grew to become more positive — and accurate.

While it’s not always easy to face your fears and ask questions, the more conversations you initiate, the more comfortable it will become. And remember that even not-so-great discussions often get a second chance at redemption because the person appreciates you reaching out in the first place.

Icebreaker questions to ask when meeting new people

Whether you’re an introvert or extrovert, you sometimes have to be the person who initiates the conversation. And if you’re trying to break into a new group environment, such as a recreational sports team or a work committee, others will most likely expect this of you.

If you’re a natural conversationalist, you may possess the communication skills to transition small talk into deeper conversations seamlessly. But if you’re among the many who feel nervous while talking to new people, your mind may go blank under pressure — especially if your nerves border on an irrational fear.

Starting a conversation is easier than it sounds. Sometimes, even a funny comment or social media meme can lead to a more introspective and engaging dialogue. But just in case nothing comes to you in the moment, keep a few solid options in your back pocket.

Here are 10 conversation starters you can use to stimulate a conversation with someone new:

1. How do you spend your free time?
2. What’s your favorite food?
3. Do you listen to any podcasts?
4. Have you heard of [movie or TV show you enjoy]?
5. What’s your favorite thing to do on the weekend?
6. Do you have any pets?
7. Do you have a favorite book?
8. What’s your favorite place to eat around [neighborhood]?
9. What would you choose if you had to choose one meal to eat for the rest of your life?
10. What’s your go-to karaoke song?

You don’t necessarily have to start a conversation with an icebreaker question. You can also share a piece of advice you’ve recently learned from a book you’re reading, mention a funny restaurant experience, or comment about something in your surroundings.

Remember: opening up the conversation is often the most challenging part. If you take the step to initiate, you’ll likely make the other person feel more comfortable contributing. Should you still feel nervous, use personal anecdotes to ease into the conversation and create jumping-off points for the other person to share their point of view.

Getting to know you questions to ask anyone

It can be difficult to judge whether some questions are appropriate for your setting. For instance, asking a manager who their celebrity crush is or about their exes is likely inappropriate in the workplace.

If you’re speaking with a best friend, on the other hand, asking personal questions about the craziest thing they’ve ever done and what their love languages are is often fine.

Here are some versatile questions to use whether you’re striking up a conversation with a stranger or initiating a chat with a new colleague:

1. What’s your latest guilty pleasure?
2. What was your favorite subject in school?
3. If you could choose a superpower, what would you pick?
4. What’s your favorite holiday?
5. When was the last time you went to a concert?
6. What was your least favorite food as a kid?
7. Do you have a favorite sport?
8. What’s the funniest joke you’ve ever heard?
9. What’s your biggest fear?
10. What was your first job?

Personal questions to ask people when establishing deeper connections

Once you become comfortable with your conversation partner, you may want to dive into more personal questions to strengthen the bond.

If you’re in a laid-back, casual setting, this could be as simple as posing funny would you rather questions. If you’re in a more intimate, you may want to ask interesting questions to get to know the other person on a deeper level.

Here are some of the best questions to get to know others personally:

1. Is there anything you dislike in your work life?
2. Do you have any pet peeves?
3. What was your dream job as a child?
4. If you could have dinner with anyone, who’s one person you’d go with?
5. Do you have a favorite childhood memory?
6. What’s the last thing that made you cry?
7. What’s your favorite season, and what does it remind you of?
8. What does a perfect day look like?
9. Do you have any hobbies?
10. If you could only listen to one song for the rest of your life, what would it be?

Fun questions to ask people you've gotten to know

Whether you’re at a work party, community event, or meeting in-laws for the first time, asking light-hearted questions is a great way to get to know the unique personalities around you. Fun questions can make others laugh, loosen up tension, and make connecting easier.

Here are several go-to questions to ease nerves and make a positive first impression:

1. What’s your favorite midnight snack?
2. Who would you choose if you could be friends with a fictional character?
3. What’s the best costume you’ve ever worn to a party?
4. What’s the best surprise you’ve ever received?
5. What’s the most embarrassing moment you’ve ever experienced?
6. If you could have any talent, what would you choose?
7. If you were stuck on a deserted island and had to choose a family member to be stuck with, who would you choose?
8. Who would you be if you had to be a character from a book?
9. What’s your funniest relationship dealbreaker?
10. If you had to live in a fiction movie, which would you choose?

Deep questions to get to know someone better

It’s normal to feel hesitant about diving into deep discussions. However, it can be a fast way to build connections through shared experiences and understanding. You may even find comfort in learning that a previous subject you felt alone in is relatable to someone around you.

It can feel vulnerable to share personal information, so when you do so, it shows the other person that you trust them. Remember: if you’re having a serious discussion with someone, always remember to listen actively and make their feelings feel valid.

Here are some examples of deep questions you can ask to build close connections and trust:

1. Do you ever feel lonely?
2. Is there anything you’re afraid you won’t accomplish?
3. What’s your biggest fear?
4. Is how you define success different today than it was when you were younger?
5. What’s the most meaningful relationship you’ve ever had?
6. Do you have any toxic traits you’re not proud of?
7. What are some difficult lessons you’ve learned from past relationships?
8. What’s number one on your bucket list?
9. What’s your favorite memory?
10. What would you like people to remember you for?

Questions to ask people at work

It’s essential to read the room when asking questions, as each person will have a different perspective on what’s appropriate. The questions you’d ask on a first date aren’t necessarily the same ones you’d ask your boss. If you’re unsure of what’s acceptable, you can always stick to work-related topics to avoid any unwanted awkwardness.

Here are some work-friendly questions you can ask your colleagues or higher-ups:

1. What’s your favorite part of your job?
2. What was your first job?
3. Do you have any side hustles or projects?
4. When you work remotely, do you work in a cafe or from home?
5. What’s something valuable you’ve learned during your career?
6. Are there any upcoming projects you’re excited about?
7. Did you ever think about trying a different career before this one?
8. What made you want to work for [company]?
9. Did you go to school to become a [job role]?
10. Do you have any tips for time management?

9 tips to manage social anxiety when asking people questions

Managing anxiety when asking people questions in both social and professional settings is a common challenge. Here are some practical strategies that might help:

1. Preparation: It's always a good idea to familiarize yourself with the topic you plan to ask about. Being prepared can boost your confidence and reduce anxiety about potential responses.
2. Practice: Rehearsing your questions beforehand, either alone or with a friend, can make the actual interaction feel more familiar and less intimidating.
3. Breathing techniques: Before and during the interaction, use deep breathing exercises to calm your nervous system. Slow, deep breaths can help manage the physical symptoms of anxiety.
4. Positive visualization: Imagine the conversation going well. Visualizing a positive outcome can help create a more optimistic mindset and increase your confidence.
5. Mindfulness: Stay present in the moment rather than worrying about future outcomes. This can help you focus on the interaction itself rather than on your anxiety.
6. Start small: If you're particularly anxious, start by asking simple questions in low-pressure situations and gradually work up to more significant questions. This way, you can build your confidence and skills over time.
7. Reflect on past successes: Think about times when you successfully asked questions in the past. This can remind you that you can handle the situation and boost your confidence.
8. Practice self-compassion: Be kind to yourself if you feel anxious. Recognize that many people experience anxiety in social situations, and it's okay to feel this way.
9. Seek professional support: If your anxiety feels overwhelming or interferes with your daily life, consider speaking to a mental health professional or certified coach. They can help you manage your anxiety and improve your social interactions.

How to get good at asking people questions

Asking good questions is a learned skill, and even the most social extroverts can benefit from brushing up on their talents. Here are some valuable tips to keep in mind for your next conversation:

Be curious

Staying curious opens you up to a world of knowledge and valuable insight. You’ll learn more about yourself and the people around you through the stories, ideas, and perspectives they share. And if you never ask questions, you’ll never know what life experiences they hold.

A hint of curiosity will help you navigate through the conversation naturally and ask follow-up questions. And in doing so, your conversation partner will also perceive you as engaged, receptive, and thoughtful.

Here are a few examples of intriguing follow-up questions:

1. What exactly do you mean when you say [idea]?
2. Why do you think [situation] upset you?
3. How did you learn about [concept]?
4. Can you give me an example?
5. Can you tell me more about that experience?
6. How did you arrive at that conclusion?

Avoid rapid-fire questions

No conversation should feel like an interrogation. A good talk flows naturally and has equal give and take. Remember: your questions are the conversation starter, not the entire show.

Ask a couple of questions to build familiarity, find common ground, and let the chatter carve its own path. Don’t be afraid of silence — sometimes, pausing provides an excellent opportunity to reflect on what’s been said.

Practice active listening

Active listening involves paying close attention to what the other person is saying and listening to understand rather than to respond. Use eye contact to show interest, and remember to give your full attention to your conversation partner.

Keep in mind that a lot of human communication goes unspoken, so you may want to practice using body language to show others you’re listening and engaged.

Work on your confidence

Here are some valuable tips for boosting your confidence:

1. Stop comparing yourself to others: Avoid focusing on those around you. Maybe your friend is naturally charismatic, or a colleague always asks the right questions to make people laugh. Everyone has different skills — including you.
2. Prepare questions: If you’re anxious about an upcoming meeting or date, brainstorm questions beforehand. You can write them down on your phone, think of possible answers and follow-up questions, or even practice with a trusted friend.
3. Practice positive self-talk: It’s easy to be unnecessarily hard on yourself or strive for perfection. Remember to look back on your progress with pride and celebrate your wins, no matter how big or small. Remind yourself of your value, and don’t forget that there’s only one you, and that’s an asset.

What to avoid when asking questions

Knowing what not to say can save a conversation from running dry. Here are a few things to avoid to foster a good discussion:

1. Avoid “Yes” or “No” questions: Closed-ended questions are a fast way to shut down a conversation. When you ask too many queries that require one-word responses, your conversation partner can’t offer a detailed answer. Instead, ask open-ended questions to allow others to reflect and provide more meaningful responses.
2. Be careful when discussing personal beliefs: Not everyone has the same beliefs, and that’s okay. Sometimes, discussing political or religious values can quickly become heated, even with people you consider friends. If you’re unsure about a topic, you should ask if they’re comfortable discussing it before posing any questions.
3. Don’t only ask questions: Don’t be afraid to share your thoughts and ideas when others ask about you. A conversation is also a way for new people to learn more about you. When you don’t share information, the other person may feel you don’t reciprocate their want for connection.

Getting the conversation started with questions

You can learn hundreds of questions to ask to get to know someone, but you still need to have the courage to ask them. Fortunately, practice makes perfect. The more questions you ask, the better your conversation skills will be.

A deep conversation builds trust and shows others that you care about their perspective and ideas. Remember to read the room, listen attentively, and ask follow-up questions to keep the ball rolling.

Published May 9, 2024