How To Get To Know Someone

How to Get to Know Someone: 53 Great Questions to Ask

Getting to know someone can be an intimidating process. Your body language, questions, and responses in the early moments will form an impression that may or may not be to your advantage in the long run. Your skills in getting to know people successfully will directly affect the outcomes of job interviews, dates, and important client meetings.
The best conversations are like a river – they flow along, even if there are a few bumps and turns along the way. It takes some practice and finesse to drive a balanced conversation that moves along naturally, and having some good questions tucked in your back pocket can help you navigate slow spots and push past mere small talk. After all, small talk, while necessary in many situations, won’t actually help you get to know someone. And then, when you see them again, there isn’t a good place to pick up where you left off!

The Art of Conversation - it is not just about you

The Art of Conversation – it is not just about you, it’s about getting to know the other person

In this guide, we will share 53 great questions you can ask to get to know someone. Asking questions helps show your conversation partner that you are interested in them as people. They are designed to help draw out and introduce meaningful, rather than superficial, conversation topics.

Many of these questions are deceptively revelatory, such as “who or where would you haunt if you were a ghost?” It may seem like harmless fun, but this question might reveal if your conversation partner has a sentimental or a vengeful streak, for example. The best part is that asking just one of these questions can open and carry an interesting conversation that will leave you far better acquainted with a new contact than everyday small talk.

 

Getting to Know Someone Question DO’s and DON’Ts

  • DON’T be afraid of vulnerability (and by that, we mean the state of being exposed to the possibility of harm). If you are unwilling to open up and show a little vulnerability, a conversation can feel stilted or fake. You have to give a little to get some in return, and quality getting-to-know-you questions almost always depend on a certain degree of vulnerability.
  • DO ease into deeper questions. Begin with the “Starter” questions below to get the conversation flowing, and then use the “Deeper” questions to transition between small talk and real conversation.
  • DO understand the context of your conversation. Questions that are appropriate for an interview or a professional setting can seem too aggressive on a date.
  • DO give the other person some time to warm up. Many people feel uncomfortable talking with new people in the beginning, so it’s best to give them some time to relax and fall into more natural conversation patterns.
  • DON’T beat a dead horse if your conversation “partner” isn’t pulling their weight in the conversation. DO make the best of it and keep asking questions if the situation requires it – you’re seated next to your narcissistic boss at a business dinner or you need to entertain a client.
  • DO listen carefully to the responses you receive from your questions. Use follow-up questions and prompts to dig deeper (Really? Why is that? How did that make you feel?) once you’ve reached a topic that you both seem to find interesting.
  • DON’T use these questions as the entire basis of your conversation. DO use them to change subjects in awkward moments when a conversation has fizzled out.
  • DO be prepared for unexpected answers to many questions; after all, you don’t really know them yet!
  • DO ask open-ended questions; yes/no and single-word answer questions (tacos or burritos?) won’t give you much meaningful material with which to engage in a real conversation.
  • DON’T forget to think through your own answers to these questions; the expectation of conversation is usually that you would be willing to answer a question in return.
Sven Raphael wearing Fort Belvedere Driving Gloves

Hobbies and personal interests are easy starter conversation topics – just ask Sven Raphael Schneider about driving fast cars!

53 Great Get-To-Know-You Questions

Before diving into the list, it is important to note that not all conversation questions are alike. Questions at the beginning of a conversation should be neutral and relatively easy to answer so that you can establish a basic level of comfort with one another. They often play off of typically light starter conversation topics such as work, family, entertainment, or personal interests, which makes for an ideal transition into deeper questions later on.

Starter Questions

  1. What do you do when you’re not working?
  2. Did you choose your profession or did it choose you?
  3. What would you do if you won the lottery?
  4. What is your favorite way to relax?
  5. What is your favorite book to read?
  6. What makes you laugh the most?
  7. What is your favorite holiday?
  8. What was the last book you read/movie you saw?
  9. What are your favorite TV shows?
  10. What is one thing you’re glad you tried but would never do again?
  11. When people come to you for help, what do they usually want help with?
  12. Who’s your go to band or artist when you can’t decide on something to listen to?
  13. What’s something you like to do the old-fashioned way?
  14. What is something you have only recently formed an opinion about?
  15. What are you interested in that most people haven’t heard of?
  16. What is something you think everyone should do at least once in their lives?
  17. What is something that people are obsessed with but you just don’t get the point of?
  18. Where is the most interesting place you’ve been?
  19. What is the luckiest thing that has happened to you?
  20. What is your biggest pet peeve with modern technology?
  21. What object have you been searching for with no luck?
  22. What social customs do you wish would just disappear?
  23. What quirky things do people do where you are from?
  24. Who or where would you haunt if you were a ghost?

Deeper Questions

Now, for the deeper questions. Each one is designed to go beyond the surface and encourage more revealing, real conversation. In fact, it might feel uncomfortable to ask some of these questions, but ultimately the goal of getting to know someone on a deeper level means putting yourself and the other person in a more vulnerable position. It’s a worthwhile tradeoff.

  1. What gets you out of bed every day? Though someone with a sarcastic sense of humor might say “the alarm clock,” this question is intended to reveal a person’s deeper motivations in life.
  2. What do you value in a friendship? This is an easy, deeper follow-up to any mention of a friend. It should also reveal what your conversation partner likes in someone they choose to socialize with, as opposed to one they have to socialize with.
  3. What do you say more often in life: yes or no? This question will show how self-aware the person is with regards to what other people ask of them. Are they a push-over or the opposite, and do they want to change it?
  4. What is on your bucket list? This is an easy question that actually digs more deeply into a person’s motivations and goals than you might initially think. It’s usually a great question for offering up common ground and many different new directions to take the conversation.
  5. What would you tell your teenage self if you could go back in time? We all make mistakes and have challenges in our youth, and many people still carry those scars (or battle the same demons) in their adult lives. This question requires more vulnerability than most, so it helps to have thought through your own response to this.
  6. What is the hardest part about raising children? For parents, children are an easy choice for a conversation topic, and the pressure to be the “perfect” parent on the surface can cause many parents to suppress having meaningful conversations about how hard parenting can be. Giving parents an opening to discuss the myriad challenges of raising children can be a welcome way to deepen a conversation and get to know a person through their daily struggles.
  7. What do you wish was different about modern parenting? Again, the expectations of modern parents can be overwhelming, and any parent is certain to have an opinion (or 12) about what they find the most daunting element of parenthood to be.
  8. What gets you fired up? This general question is highly open-ended, and therefore a little bit less intimidating to ask. The responder can choose how deeply they’d like to get into the subject. It can easily be modified to be more specific, which you may want to do if you are in a place in which the response might involve controversial subjects. If you leave it open-ended, be prepared to talk about things that the responder is really passionate about, such as politics or a quirky hobby.
  9. What mistake do you keep making again and again? Questions about failure are some of the most revealing ones out there and will speak volumes about the character of the kind of person you are talking to.
  10. What have you created that you are most proud of? Most people are willing to talk about their accomplishments and this question will help draw out what people are proud of in their lives.
  11. What’s the best thing you got from your parents? To clarify, this could mean a gift, a character trait, or an important life lesson. This question will often reveal the nature of the respondent’s relationship with their parents and how they view their childhood in retrospect.
  12. What’s one responsibility you really wish you didn’t have? This question is a quick way to find out what people feel are unnecessary burdens in their lives, and they can range from imposed (job changes) to self-inflicted (I wish I hadn’t bought a house). Finally, they can speak to how people approach their responsibilities in life – are they powerless victims or are they aware of the choices they have?
  13. What’s the best and worst thing about getting older? Aging can be a sore spot for many people, and the passage of time can prompt musings on missed opportunities, gratitude, and hopes for the future.
  14. What chance encounter changed your life forever? Most people have experienced a lucky encounter in their lives, and this question often leads to funny, sentimental, or meaningful life stories.
  15. What do you regret not doing? Regret can be a very powerful feeling, and it tends to be universal. Most people won’t have an issue coming up with an answer (or several) to this question, but since it is negative in nature it’s wise to balance it with a positive question before or after it.
  16. Do you believe in second chances? This potentially sensitive question is a good follow up to a conversation about difficult interactions or relationships. It speaks to everyone’s desire to be offered a second chance in their own lives while finding the capacity to forgive other people for their transgressions.
  17. Do you want to retire to live or live to retire? It can be interesting to discover who believes that all enjoyment – travel, hobbies, etc – have to wait for retirement, while others are determined to live well regardless of their employment status.
  18. What are some things you wish you could unlearn? Everyone has bad habits, right? Commiseration is an easy way to connect with a new acquaintance and learn more about how they tick.
  19. What do you wish your brain was better at doing? This gives people an easier way to share their weaknesses because the question deliberately uses “your brain” instead of “you”. That small degree of separation helps reduce the sensitivity of the question without shying away from the subject itself.
  20. What or who couldn’t you live without? This question strikes right at the heart of who and what a person values in their life, and they will usually add in why. If not, ask!
  21. When do you feel the most confident? The response to this question can go in many interesting directions, perhaps to a certain outfit or in a specific setting.
  22. If a crystal ball could tell you anything about your future, what would you want to know? You can ask this question in conjunction with #25.
  23. If you could change one personal decision in your past, what would that be? The opposite of #15, this question reveals how people feel about past actions they have made.
  24. What goal are you working on now? Even if they don’t have elaborate annual goal planning sessions, everyone has a goal. This open-ended question gives you conversation partner considerable flexibility in how they answer, which makes it an easy one to ask.
  25. What scares you about the future? Everyone has fears, and this is an interesting way to narrow the question down and find some common ground.
  26. When was the last time you cried? Doubtless, this is a very personal question and choosing the right time to ask it can be tough. However, it does strike right at the heart of the other person’s deepest pain or frustration.
  27. Do you believe people are at the whim of destiny or that they can create it themselves?
  28. Who is someone that you miss having in your life? Deaths or departures of close family and friends can have a lasting impact on a person’s emotional life, and since the experience is fairly universal, it can be a good way to find common ground with a new acquaintance.
  29. What question do you always want to ask people but don’t have the courage to ask? Social norms can be powerful, but they can also blunt a conversation in the name of being “polite”. This question can help reveal other people’s frustrations with social norms and open the door to discussing taboo but interesting topics.

Conclusion

Getting to know someone takes effort, and these questions offer you a simple way to dig deeper, faster. What questions do you find are the most helpful in getting to know someone? Do you have special questions for dates, interviews, clients and colleagues?

Summary
How to Get to Know Someone: 53 Great Questions to Ask
Article Name
How to Get to Know Someone: 53 Great Questions to Ask
Description
Be a great conversationalist and learn these 53 great questions you can ask to get to know someone.
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Gentleman's Gazette LLC
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4 replies
  1. Ian Ridd says:

    Mmm … not sure how this would go down in England. Even your starter questions sound dangerously intrusive to the English ear. Over here we mostly talk aimlessly about the weather. That works well, because English weather is highly variable, and if you are lucky it will change dramatically during the conversation, enabling you to start talking about it all over again.

    Reply
    • Simon says:

      I would agree, most of these would lead to a raised eye brow and a turned back, but that could just be the Midlands for you. However I feel some of the “Deeper questions” they could open up to the idea of leading conversations, which i don’t mind, as the article says it can take you to something you can pick up on when you see them again.

      Nice article all in all though.

      Reply
  2. Christopher Lee says:

    Every month, I have to lead virtual discussion groups designed to team build. It rotates in terms of who leads the discussion, and your list will be quite helpful in giving me years of conversation starters for this! Good timing.

    Reply

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