Questions to Ask to Get To Know Someone: 60 Great Inquiries

Humans evolved to be social. 

No matter your personality type or extroversion level, building relationships with others and communicating well to strengthen these connections is priceless to your social health.

As most people spend a fair amount of time at work, this import extends to workplace relationships. You’ll feel more engaged and productive if you connect well with your managers and coworkers, empathizing with them and feeling like you belong.

The best way to build these meaningful relationships is by honing your communication skills. The more you learn from others, the closer you’ll feel to them — that’s why knowing what questions to ask to get to know someone is so important.

If you can’t probe someone further or follow up on a previous conversation, you’ll never enjoy relationships that go deeper than small talk.

Asking questions means you’re interested in others, curious, and love to learn. It also shows people you’re actively listening to what they’re saying, which makes them feel cared about and understood. 

Asking questions doesn’t always come naturally. Most people talk about themselves a lot — about 30–40% of the time, according to a study by the University of California. Why? Because it feels good. This study found that your brain releases dopamine when you talk about yourself. 

But this also happens when you ask others questions — they get the same rush of feel-good hormones. It also makes people like you more because you’ve shown interest in them.

For some people, asking questions feels uncomfortable — especially when you’re talking to someone new. This discomfort might stem from social anxiety, but it could also be that you think you don’t have good questions to ask. 

A recent study found that people tend to be pessimistic about how strangers perceive them — they fear new people don’t want to talk to them or that they won’t ask good questions. This negative impression might stop you from starting conversations or cause you to end them prematurely. 

But the study revealed some good news: switching to an optimistic attitude is learnable. And after a week of starting conversations with strangers, participants felt less awkward, more confident, and expected rejection less frequently.

The more they initiated conversations, the longer the positive effects lasted. 

If starting a discussion makes you uncomfortable, jump into the deep end. You might surprise yourself with how well you wade the waters. 

1. What’s your favorite way to spend free time? 

2. What’s your favorite place to travel to?

3. Have you heard of [new popular tv show]?

4. Do you have a celebrity crush? 

5. Do you have a favorite movie?

6. Do you have a favorite book? 

7. What’s your favorite place to eat around here?

8. If you had to choose one cuisine to eat for the rest of your life, what would you choose? 

9. What’s your go-to karaoke song? 

10. Do you have a LinkedIn profile?

Remember: you don’t have to start a conversation with a question — they might beat you to it. Share facts about yourself to make them feel more comfortable contributing information, and use personal anecdotes as jumping-off points to turn the conversation around and learn more about them. 

If you’ve made a good first impression and you’re hitting it off with your conversation partner, personal questions can help strengthen the bond. Here are the best questions to get personal — remember to approach these carefully when at work: 

1. Do you have any good first-day memories from a new job?

2. Do you have any pet peeves?

3. What’s your dream job?

4. What’s your favorite comfort food?

5. What’s your biggest fear?

6. What’s the funnest thing you’ve done on vacation?

7. What was your favorite season of [popular television show] and why?

8. What does a perfect day look like?

9. Do you have a hidden talent?

10. If you could only listen to one song for the rest of your life, what would it be?

If you’re at a party, doing icebreakers for a group meeting, or introducing in-laws for the first time, creative questions that pull out people’s unique personality traits or experiences are a great way to loosen everyone up and connect. Here are the best questions to ask:

1. What’s your go-to midnight snack?

2. If you could go camping with any fictional character, who would it be?

3. What’s the best costume you’ve ever worn to a party?

4. What would be your perfect surprise party?

5. What’s the most embarrassing moment you’ve had at school?

6. If you could sing with any musician, who would you choose?

7. Which family member would you choose to be stuck on a deserted island with?

8. What side of the pineapple-on-pizza debate are you on? 

9. What’s your silliest relationship dealbreaker?

10. Which book would you choose if you lived in a fictional novel?

1. What’s your favorite part of your job?

2. What was your first job?

3. Do you have any side hustles?

4. Do you have a favorite café you work at?

5. What personal values have to be reflected within your employer’s work values?

6. Are there any upcoming projects you’re excited about?

7. Are there any work traditions here you love?

8. How did you end up at [company]?

9. Did you study to become a [job role]?

10. How do you stay on top of all your work?

Similar to how people feel uncomfortable starting conversations with strangers, it’s common to feel hesitant about diving into deep discussions. But this depth helps you better relate to others because they might discuss experiences you felt alone in.

You also show you trust each other with more vulnerable information. Here are some examples. Again, remember to approach these carefully with coworkers:

1. Do you ever feel lonely?

2. What’s your biggest aspiration?

3. What’s your biggest fear?

4. How do you define success?

5. What’s the most meaningful relationship you’ve ever had?

6. Do you have any toxic traits?

7. What are some lessons you’ve learned from past relationships?

8. What’s number one on your bucket list?

9. What’s your biggest regret in life?

10. What would you like people to remember you for?

Be curious about what the other person has to say by asking follow-up questions to clarify their opinion, understand their thought process, and learn more. Your conversation partner will also perceive you as more engaged and receptive. 

Here are a few examples:

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?

2. Avoid rapid-fire questions

A verbal exchange isn’t an interrogation. A good conversation is about give and take. Your questions should be the conversation starter, not the entire show.

Ask a few questions until you find common ground, then let the chatter flow naturally. If the conversation has a natural pause, find comfort in silence or fall back on another question.

3. Practice active listening

Active listening involves using tricks, like telling yourself to retain five facts from the conversation, and body language, like eye contact and leaning in, to increase your focus.

Since up to 93% of communication is unspoken, it’s worth perfecting these body language skills to retain more from others and show you’re listening. 

4. Work on your confidence

The more confident you are, the less hesitant you’ll be to ask questions. And the more questions you ask, the more confident you’ll feel. So working on your confidence outside of conversations will help, as will starting more chats. 

Here are some tips to boost your conversation confidence:

1. Stop comparing yourself to others: Don’t focus on the people around you. Maybe your sibling is naturally witty, or a coworker has a talent for asking all the right questions. We all have different skills — focus on yours. 

2. Prepare questions: If you have an upcoming meeting or date, think of some questions ahead of time. Do whatever works for you: write them down, think of possible answers and follow-up questions, or even practice with a friend. 

3. Practice positive self-talk: Look back on your progress regarding question-asking and conversational skills. Maybe you’ve gained more confidence to participate in meetings or improved your small talk skills in social situations.

   All progress is worth celebrating, and these celebrations will motivate you to continue improving. 

1. Avoid “Yes” or “No” questions: These are considered closed-off questions — the person can’t give detailed answers, so the conversation often goes nowhere. Instead, ask open-ended questions to encourage people to develop their ideas and give you more information to bounce off of.
2. Be careful when discussing political and religious beliefs: This is especially important for conversations with strangers or coworkers. These are heated topics that might make people uncomfortable, so save them for those you’re familiar with who you know enjoy these types of conversation. 
3. Avoid only asking questions: Questions start the discussion but shouldn’t be used to carry the conversation. Remember to also share information so they feel they can trust you and that the conversation isn’t one-sided.