Best 220+ Questions to Get to Know Someone and Build Real Connections

Questions to get to know someone, getting to know someone new—really getting to know them—can be exciting, especially for extroverts, if the circumstances are right. But it can also seem daunting. This is particularly true for introverts, or anyone facing a new situation and needing advice on a first date, a new job, a new city, or even a new identity (like becoming a parent for the first time). The best way to navigate this is to always pose the right questions in order to truly understand the person.

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The Art of Conversation: Best Questions to Ask to Get to Know Someone

Conversation is not just about talking, but listening as well. Nobody can know a person well without asking them some serious and in-depth questions. Dr. Wayne Pernell, a clinical psychologist who assists individuals to achieve more success and fulfilment in their life and work, says that it is not easy to get to know a person, be it in a new relationship, a business meeting, or just a casual environment. He recommends that one should not start off with general issues, such as the weather, which would not contribute much. Rather, ask questions that show how the individual is, his/her thoughts, and experiences. Listening to them and showing interest in what they have to say is also important. This method establishes a real relationship.

Here are a bunch of questions that can inspire a real connection. Now it’s your turn to bring out the best in the people you’re interested in getting to know.

Best Questions to Ask to Get to Know Someone

Questions about what He/she likes/dislikes

According to Pernell, one of the methods to probe personally without being intrusive is to ask a person what he/she likes or does not like. For example, even asking someone about their favourite snack is asking them to recall something, and it opens the door to conversation. “You can know what they like, what trips they have made, and what their background is,” she says.

What’s your favourite snack and where did you eat it?
What’s your favourite childhood cartoon?
What’s the star recipe for your family meals?
What is your favourite place on earth?
What’s your ultimate dream vacation spot?
Which country particularly interests you?
What’s the longest flight you’ve ever taken?
Which is your favourite TV show currently?
Which presenter gives you a bad feeling?
What’s the worst movie you’ve ever seen?
What was the last movie you watched in the theatre?
What is the first movie you remember seeing in a cinema?
What is your favourite all-time movie?
And what’s the best TV series you’ve ever seen?
Are there any series that you re-watch every so often?
Which fictional character do you identify with most?
What’s the best concert you’ve ever been to?
What was the first group or artist you were a fan of?
What’s the worst date you’ve ever been on?
Do you prefer to be cold or hot?
What’s your favourite song to belt out at karaoke?
What’s the best book you’ve read this year? (Here are the best books of 2026 )
What book made a lasting impression on you during your childhood?
Where do you especially like to read?
What is the one item of clothing you couldn’t live without?
What item of clothing would you never wear?
What’s the craziest time you’ve ever dressed up?
Take three objects to a deserted island. What would you take?
Assuming you had an opportunity to save one physical item in a fire, what would that be?
What is your material possession that has the most emotional value?
What bothers you most about a stranger?
What do you most like to do during your free time?
Which are the most boring or unpleasant duties to you?
What do you want to learn or attempt the most?
Are you interested in extreme sports?
Which sport do you enjoy most as a spectator?
In which sport do you have the most natural talent?
Do you prefer team games or individual games?
What is the location in the world that you would like to see, and why?
How do you define success?

Questions about hopes, dreams, and fears

Simple getting-to-know-you questions can really spark deep and emotional conversations, especially when they tap into a person’s fears, regrets, hopes, and dreams. This view is also supported by renowned relationship expert and famous Therapist Esther Perel. According to her, good questions are those that are simple, open, and allow the respondent to express their inner world. She emphasizes that the conversation should be free of clichés, because repeated questions do not create interest or trust. Perel also believes that the questions we should ask should be those that we feel comfortable answering ourselves. In this way, the conversation is not just an exchange of information, but also gives the relationship a real and human colour, which is essential for getting to know a new person. Here are some questions you can use:

What’s at the top of your wish list?
What are you most grateful for?
What do you regret most in life?
What do you fear most?
What are you most passionate about?
How do you like to spend your free time?
What would your perfect day be like?
What is your dream life like?
What’s the typical thing that can ruin an ordinary day?
If you were to earn 10 million euros right now, what would you invest it in?
What is your most recurring nightmare?
Have you ever dreamed of something that later came true?
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Have you ever had a premonition?
What scared you the most as a child?
Which disease scares you the most?
Do you have hope for another life or a sense of transcendence?
Are there any experiences that make you think that there is an afterlife?
Which historical figure do you admire?
What change in society do you think would make us better?
Which of the events that are happening gives you the worst feeling?
Who in your family has given you the most beautiful life lesson?
If you had 10 million followers on Instagram, what topics would you talk about?
What cause are you particularly passionate about?
What injustices make your stomach churn the most?
What excites or thrills you the most right now?
What would you most like to learn or try?
What makes you feel most proud or satisfied?
What do you value most in a friendship?
What makes you feel happiest and most fulfilled?
What dream do you still have yet to fulfil?

Questions that spark a (friendly) debate

One way to keep a conversation flowing is to ask questions about a topic that might inspire controversial answers. “Start a friendly debate that sparks a fun and unusual conversation,” suggests Kate Maclean, dating expert at Plenty of Fish. You’ll probably want to avoid heated political debates from the start; rather, even silly hypotheticals can lead to ” a quirky, light-hearted conversation that can help defuse any situation .”

To do this, try it like this:

What’s your favourite urban legend that you believe to be true?
Would you rather live without the internet or without taking a bath?
Which was the best decade for music?
Is it ever okay to lie?
Who is the most overrated celebrity?
What is the worst seat on an airplane?
What do you think is the most irritating behaviour people have in public?
Are avocados overrated?
Who do you want to invite to dinner, somebody in the past or in the present?
What would you do tomorrow if you won a million euros today?
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Is a hot dog a sandwich?
Do you like dogs or cats, and why?
Were Ross and Rachel really in love?
Are you more of a wine or beer person?
What do you think about banning smoking on terraces?
And what about shops opening on Sundays?
What do people who always wear the same colour tell you?
Are superhero movies ruining cinema?
Do you think a boss can be a true friend?
Is it dangerous to post vacation photos with an empty house?
What would you do if the power went out across the entire planet?
Are video games dangerous for children?
Who is the real queen of pop?
Are TV series now better than movies?
Tortilla, with or without onion?
Was there room for Jack on the Titanic’s raft?
Would you buy an electric car?
Have you considered going vegan?
How much are you willing to pay to go to a Michelin-starred restaurant?
Remote work or in-person work?
What do you like most about your country and what do you like least?
What do you think of social media: is it a blessing or a curse?
Which book or movie do you think is overrated or underrated?

Questions about family and community

For some, questions about family can be emotionally charged or very difficult. However, gently unravelling the ties that bind a person’s family, friends, and other community relationships can be both revealing and uplifting. For example:

Who is the most valuable person in your life, and why are they so valuable?
Who is the person who makes you feel most at home?
Do you have a mentor?
Did you ever terminate a friendship? Why, then, did you do it?
How many close friends is ideal?
Do you believe in soulmates?
What’s the best advice your father or mother has ever given you?
What made you most nervous about your siblings when you were little?
Did your grandparents tell you stories about their youth?
Do you have the typical uncle who always causes trouble at weddings?
Did you have a nickname in school?
What do you admire most about your family?
What do you like to do most with your friends?
What is it that most unites you with your community or your culture?
What would you most like to change or improve in your environment?

Questions about personal history

Sometimes, a direct question can reveal how people perceive themselves and how they want to be perceived by others. Furthermore, answers to these fundamental questions are unlikely to emerge spontaneously in the course of a casual conversation. Consider these questions that delve into someone’s personality, personal history, and what they consider to be the most fundamental aspects of their being:

What’s the best compliment you’ve ever received?
What do you want people to remember about you during your funeral?
And what song would you request to be played at your final farewell?
What is something people would never guess just by looking at you?
What makes you laugh the most?
Have you ever taken a life-changing decision?
What was the happiest day of your life?
What do you like most about yourself?
What did your teachers say about you on your report card, and is it still true?
What would you like to change about yourself?
What decision in your life do you regret the most?
Do you identify with the stereotype of your zodiac sign?
What do you most regret not having done?
Is there something you didn’t dare to do back then that you now feel capable of?
What trait of your personality has changed the most over time?
What personal change are you most proud of?
What did you do when you were young that you wouldn’t dare do now, not even as a joke?
What bores you to death?
What song can’t you listen to without crying?
And which one do you wear to lift your spirits?
What would you say was the most difficult time of your life?
If you could freeze your life at a specific age, what would it be?
If you could travel through time, would you go to your past or your future?
What was the first photo you posted on Instagram?
And the last one?
Would you trade your life for that of someone you know?
Which celebrity would you swap places with for 24 hours?
What book has changed your life?
What childhood values do you still hold onto?
On what important issues have you changed your opinion the most?

Questions about the essence of personality

Questions about personality invite us to look deeper into those around us. What defines them? How do they react to the world? These inquiries not only break the ice but can also spark fascinating conversations. Beyond the typical questions, listening attentively to the answers is key. We all long to feel seen and heard, and our responses matter.

What are you most passionate about in life?
What scares you the most or makes you nervous?
What makes you happiest?
What makes you the angriest or most outraged?
What inspires or motivates you the most?
What embarrasses you the most or makes you feel guilty?
What surprises or amazes you the most?
What relaxes or calms you the most?
What do you find most fun or entertaining?
What excites or thrills you the most?
What is your happiest memory?
What is the biggest challenge you have faced?
What do you value most in a friendship?
What is your favourite book and why?
What important lesson have you learned recently?
What motivates you to get up every morning?
How would you like to be remembered?
What is your greatest achievement so far?

Questions about work

Depending on the setting, work-related questions can be the best icebreakers and ways to spark a lively conversation. For best results, go beyond the usual interview or refrigerator questions. “Don’t just make a list of what you’re supposed to ask,” says Narenberg. “Really listen to the person’s response. Everyone wants to feel seen and heard and that their answers matter.”

What’s the most exciting thing about your job?
What do you want people to say about you at your retirement party?
What is the most important thing you have done at work?
What is your ideal work-life balance?
What’s the best professional advice you’ve ever received?
What did you think was a setback in your career that actually turned into an opportunity?
What are the most important qualities of a leader?
How did you get your first job?
Have you made any real friends at work?
If you could change professions tomorrow, what field would you choose?
What do you value most in a co-worker?
What is the least tolerable thing you can tolerate in a boss?
What motivates you most in your work?
What frustrates or stresses you the most at your job?
What skills or knowledge would you like to improve or learn?
What advice would you give to someone who wants to enter your sector?

Questions to ask to get to know someone on Tinder

Or on any dating app, you know what I mean. In this environment, the key is to be clear about what nobody likes to see happen on Tinder and, above all, to downplay the importance of the conversation until you’re seriously considering meeting up. In other words, the most appropriate questions are light-hearted and suggestive ones related to the photos or the profile text, which allow you to learn small details about the other person and also flirt with a bit of originality—it’s all about having fun. Oh, and absolutely FORBIDDEN to start with “What are you looking for?” If the person on the other end is even remotely interesting, they’ll find it incredibly boring.

Can you imagine if we got along?
From 1 to 64, what are the chances that we will be having coffee tomorrow at this time?
Are you a very direct person or can I keep talking nonsense?
If we were on First Dates, would you still be at the restaurant?
And on Temptation Island, would you prefer to go as a couple or as a temptation?
What was the most absurd date you’ve ever had online?
What do you hate most right now with all your heart?
Do you believe in extraterrestrials?
Have you ever insulted a celebrity on Instagram?
Which concert would you like to be at right now?
Are you planning a trip?
What plan would you like best for your pre-wedding farewell party?
If we had a cat, a dog, and a canary, what name would you give each one?
What has been the most embarrassing moment of your life?
What do I have to give you so that you’ll send me the photo of your First Communion?
What series are you watching right now?
What’s the weirdest thing you’ve ever eaten?
What superpower would you like to have?
What are your hobbies during your free time?
What type of person are you most physically attracted to?

Questions to get to know someone you really like

We move on to the next phase. You’ve met up many times, things are going well, and you want to learn more about the other person so that these conversations you’re enjoying so much don’t lose their spark and bring clarity to your potential future. Obviously, you can use many of the questions we’ve raised in the previous categories… These are simply more direct and, at a certain point, important for understanding where each of you is headed.

When was the last time you felt true pleasure?
Do you think a lot about monogamy or open relationships?
When you feel jealous, do you get angrier with the other person or with yourself?
Would you consider living in another country if a job opportunity came up?
Are any exes, or could they become, great friends?
Have you ever been to therapy? Would you like to?
Have you discovered any behavioural patterns in your parents that worry you?
Would you go on vacation with just friends and without your partner?
What do you think your family would think of me?
What would you tell your 10-year-old self?
And what do you think your 10-year-old self would say about your current life?
Picture us together in 10 years: what do you see?
Who are you?
What do you like most about yourself?
What is the one thing you would most like to change about the world?
What kind of music makes you feel good?
What do you value most in a relationship?
What scares you the most or makes you nervous?

Final Thoughts

The questions also make us conscious of the fact that to know someone well is not just a matter of formalities but also asking interesting, meaningful, open-ended questions that forge a true connection. A conversation should not be an ask, but rather a listen with all your heart. Knowing likes and dislikes, dreams and fears, family, and personality of a person enhances knowledge as well as creates trust. Ask questions you know how to answer, and do not use repetitive and general questions. That makes the discussion refreshing and pleasant. The trick of good relationships is that you make the other person feel valued. And finally, no matter how light or deep the talk is, when both of you feel seen, heard and understood, you are actually deep into it.

Best Curious And Original Questions to Get to Know Someone: Meaningful Conversation Starters

The Art of Conversation: Best Questions to Ask to Get to Know Someone