25 Best Questions to Ask to Get to Know Someone

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Meeting new people and engaging in easy-flowing conversations can be refreshing and exhilarating.

However, we’ve all experienced those moments when we find ourselves struggling to connect with someone, leading to awkward chats that leave us feeling drained.

While not every conversation can be a winner, there are expert-approved tricks that can help improve your conversation skills, making it easier to develop and strengthen relationships with others.

Here, we’ll investigate the 25 best questions to ask to get to know someone, taking your conversations from small talk to real talk and revealing the unique aspects of a person’s personality.

Starting with Breadth Questions: Laying the Foundation for Deeper Conversations

When first meeting someone, it’s important to begin with breadth questions—those that cover a wide range of topics without delving too deeply into any of them. These questions help to break the ice and take the conversation from small talk to real talk. Some examples of breadth questions are:

  1. What do you do for a living?
  2. Where are you from?
  3. What are your hobbies?
  4. Do you have any pets?
  5. What’s your favorite type of music?

These questions may seem basic, but they’re an essential starting point for getting to know someone. By keeping the conversation light and non-invasive, you’ll make the other person feel more comfortable and willing to open up.

Open-Ended Questions: Encouraging Deeper Conversations and Bonding

Moving beyond breadth questions, it’s time to dive deeper into the conversation by asking open-ended questions. These questions allow the other person to share more about themselves and their experiences, leading to a deeper bond between the two of you. Some examples of open-ended questions are:

  1. What’s the most interesting thing you’ve learned recently?
  2. What’s the best advice you’ve ever received?
  3. What’s a challenge you’ve overcome, and how did you do it?
  4. If you could travel anywhere in the world, where would you go and why?
  5. What’s something you’re passionate about?

Asking these types of questions not only helps you get to know the other person better, but also encourages them to share personal information, which can strengthen your relationship.

Creating a Warm and Inviting Atmosphere

During initial conversations, it’s essential to be inviting and warm, making the other person feel comfortable and at ease. This can be achieved through body language, tone of voice, and the types of questions you ask. Avoid critical or invasive questions, as these can make the other person feel defensive and less likely to open up. Instead, focus on positive, supportive questions that allow the person to express themselves freely. Some examples include:

  1. What’s something you’re really proud of?
  2. What’s a talent or skill you wish you had?
  3. What’s a book, movie, or TV show that has impacted your life?
  4. What’s your favorite way to unwind after a long day?
  5. What’s your favorite thing about your job?

Taking the lead in vulnerability by sharing your thoughts, feelings, and experiences can also encourage the other person to do the same, deepening your connection.

Asking Follow-Up Questions: Deepening Understanding

As the conversation progresses, it’s important to ask follow-up questions to deepen your understanding of the other person. This shows that you’re actively listening and genuinely interested in what they have to say. Some examples of follow-up questions include:

  1. How did you get into your line of work?
  2. What’s your favorite part about living in [their hometown]?
  3. What kind of projects are you currently working on?
  4. How did you become interested in [their hobby]?
  5. What’s your favorite memory from your travels?

Asking follow-up questions not only deepens your understanding of the other person but also creates a more personal connection by exploring their values, dreams, and interests.

Unusual Questions: Revealing Unique Aspects of a Person’s Personality

Asking unconventional questions can help reveal unique aspects of a person’s personality, making the conversation more engaging and memorable. These questions can range from funny and light-hearted to thought-provoking and introspective. Some examples of unusual questions include:

  1. If you could have dinner with any historical figure, who would it be and why?
  2. If you could only eat one food for the rest of your life, what would it be?
  3. If you could have any superpower, what would you choose and why?
  4. What’s something you’ve always wanted to try, but haven’t yet?
  5. If you could go back in time and give your younger self one piece of advice, what would it be?

These questions not only create engaging conversations but also give you a glimpse into the other person’s thoughts, beliefs, and values, helping you better understand who they are.

Taking the time to ask thoughtful, open-ended questions is key to getting to know someone on a deeper level. By starting with breadth questions, creating a warm and inviting atmosphere, and progressing to more in-depth and unusual questions, you’ll be better equipped to develop strong relationships and make meaningful connections with others. So the next time you find yourself in a conversation with someone new, remember these 25 best questions to ask and unlock the art of conversation.

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