25 Questions To Help You Get To Know Someone Deeply

Humans are a naturally social species and healthy communication helps create connection and can make life feel purposeful. Even the most introverted individuals may find themselves looking for deep, meaningful connections with other people – whether that’s romantic, platonic, familial, or any other relationship.

Often, though, people find themselves feeling nervous or overwhelmed by the idea of idle chat and small talk. So, how do you break down the barrier of awkwardness that can come with new introductions?

It can be as simple as asking the right questions to get to know someone. Open-ended questions can get to the heart of someone's values, personality, and beliefs about the world without feeling intrusive.

Questions can make conversations more interesting

Oftentimes, asking questions to acquaintances or friends helps you get to know each other and become comfortable in each other’s company and can serve as thought starters to get the conversation going. When the person you’re with answers with enthusiasm and openness, the conversation might lead to deeper and more personal topics.

Remember, though, that everyone has the right to stop talking or refuse to answer questions that feel too personal or invasive, and people shouldn’t be pushed to give an answer they’re uncomfortable with. It’s important to be respectful of other people’s comfort level when it comes to conversation and to abide by the boundaries they put in place when they’ve stopped talking.

35 questions to help you get to know someone deeply

Whether you're trying to strengthen a friendship that you've had for years or become more intimate with your significant other, well-chosen questions can spark a conversation that can help you get to know them and their life story in ways you never have before.

Here are 35 questions that you can ask to engage others in meaningful conversation.

What achievement are you proudest of?

Asking about what someone is proud of can reveal a lot about their personal values. Some people might consider their job performance to be their biggest achievement. Others might put more value on relationships with friends and family. Others may hope for certain achievements in the future. Having your friends describe these accomplishments can help you learn a lot about them on a deeper level.

How did you react to your biggest mistake? 

Taking an honest look at past mistakes, or your biggest regret, as well as the sincerity of your efforts to improve yourself, can help you learn more about yourself as a person. Asking this allows you both to explore how the responding party is trying to better themselves.

If you could go back and change one decision in your life, what would it be? 

Though similar in theme to the previous question, this focuses less on mistakes and more on past life events. The answer may tell you how this person has changed over time, and how their values and beliefs have shifted through natural and unnatural life transitions.

What is your biggest dream in life?

Where does this person want to go in life? And what’s on their bucket list? They may respond with dreams for their career, their living situation, or their future relationship goals such as marriage or parenthood. Asking about future aspirations can help you decide whether or not you can visualize yourself as a part of another person’s life in the long term.

What was your childhood like? What’s your favorite childhood memory? Your worst memory?

A person's childhood can give you a lot of information about who they are, as can their feelings about that childhood. Maybe they have a favorite memory or a lot of happy memories from when they were a kid, such as birthdays sports, or a favorite teacher, but they have not had the chance to open up about how they were raised. Conversely, they may have had unpleasant experiences and wish to do better for themselves and their loved ones as an adult. Antonia Hall, author of The Happy Human Playbook: A Practical Guide to Healing Body, Mind and Emotions with Joy and Pleasure, reports that asking questions about childhood can reveal a new side of your friend.

What's one thing that you wish people understood about you?

Sometimes, appearances are deceiving, especially with the rise of social media. Some people may feel that they need to conform to a certain standard for their public image to remain intact, while others may feel misrepresented by the public perception associated with them. Additionally, there’s often no such thing as knowing everything about another person. This question may allow you to see what someone values about themselves that others may not see, and it can create a supportive environment for the other person as well.

What is something you are working to improve in yourself?

Though it can be uncomfortable to consider, understanding the things that we consider to be areas of improvement in our lives can greatly improve how we interact. Discussing the negative aspects of your personality can help both parties of a relationship to better understand each other and how you fit (or don’t fit) into each other’s lives. It can also help one another feel supported in their quest to be the best versions of themselves.

What event in your life has shaped you most as a person? How did it do so?

Whether it was an early positive influence or occurred later in a person’s life, asking about important moments in life can offer you valuable insight into a person's past. This defining moment in their mind may help inform their opinion about many decisions and behaviors as the friendship progresses that would otherwise be mysterious.

Have you ever treated a person in a way that you regret?

The answer can reveal much about what someone considers to be the right and wrong ways of treating others. It can also tell you more about how you might expect to be treated in the course of the friendship.

Do you think it's possible to be "just friends” with someone of another gender?

It is important to define the nature of a relationship and the expectations you have for each other from the outset, especially in the often socially questioned scenario of a cross-gender friendship. Though it is perfectly possible for people of all genders to be friends, some people perceive those relationships differently due to unhealthy exposure to flawed expectations about romantic interaction. If this is the case, knowing from the outset can help you set healthy boundaries in the relationship.

Would you rather be rich and lonely or financially destitute with lots of great family and friends? Why?

This is another question that may speak volumes about a person's current priorities. Some people may place more value on personal stability while others may focus more fully on rich, interpersonal lives. Knowing which your responder prioritizes can help you understand their boundaries in the relationship.

What role does alcohol play in your life?

Being under the influence of a substance often leads to the loss of a person’s usual inhibitions and “filters," meaning that they are more likely to speak and act without considering the consequences. Understanding how a person acts when intoxicated (and how often they are in that state) can help you determine boundaries when it comes to behavior and the use of substances.

If you are struggling with substance use, contact the SAMHSA National Helpline at (800) 662-4357 to receive support and resources. Support is available 24/7.

If you could change one thing about yourself, what would it be and why?

Once again, this is a question that examines what someone values, what they may perceive as a flaw in themselves, and what they might be doing to improve themselves. It can also offer you a way to understand what topics you should be sensitive to when talking to and about this person.

If you knew you would die tomorrow, how would you spend today?

Considering your mortality often prompts you to confront the things that you most value but might not consider to be immediate priorities, because you may assume you have plenty of time to address them later on.

What does happiness mean to you? 

Happiness is subjective, so the answer to this question can show you what your responder considers happiness to mean, and what makes them happy, both in the short term and the long term. It can help you see what allows them to feel content and what excites them.

Have you ever been in love?

Everyone’s experience with love can be different. While some people may consider romantic love to be vital and pivotal in their lives, others may more greatly value having fallen in love with a hobby, career, or group of devoted friends. All healthy forms of love are valid, and they can give you insights into a person’s life.

When you're home alone, and nobody else is around, how do you like to spend your time?

A person may be most relaxed when they don’t feel that they are being observed, so understanding how your responder acts when they are alone can help you to see what makes them feel content, safe, and fulfilled.

What do you want people to say in your eulogy?

This can show you what a person wants to accomplish in their life, as well as the kind of impression they hope to make on others.

If you could have a conversation over coffee or food with anyone living or dead, who would it be and why? 

Whatever the response is for this question, you can discover the kind of person your responder admires the most, revealing attributes that they value above all. This can be an effective way to find out more about their interests as well. You might even take the question a step further and ask who they would like to be trapped on a deserted island with to find out who they would want to be around when it matters most. 

Do you think you're a genuinely good person? 

This question is helpful in sorting out your friend's standards of worth and what it means to be a “good” person at all.

How and why did you choose your current profession? 

Asking this question can help you understand whether this person is content with their path in life. Are they making steady progress towards their goals, or ready to mix things up at any given moment?

If money were not an issue, how would you spend your time each day?

The business of earning a living often gets in the way of personal ambitions. Learning about the hopes and dreams your friend may hide underneath the routine of daily life can reveal a lot about their interests and personality. 

How do you lean politically?

A reasoned, calm discussion of opinions and personal views may help you and your responder understand each other’s worldview, which can point you toward core values you both hold for quality of life and the equity of people across cultures.

What's one thing that you do on a regular basis that nobody knows you hate doing?

This is a unique way to discover someone's likes and dislikes, as well as how much they are willing to give up for others’ needs or for a cause they deem necessary.

What is the most awe-inspiring place you’ve ever visited?

Learning about the kind of place that makes a person instantly light up can tell you a lot about the things they appreciate in life and potentially the kinds of traveling they enjoy doing.

Do you have similar interests?

Which three words describe you best? What about five words?

Hearing a person describe themselves in only a few words can reveal what they truly think of themselves and how they want others to perceive them. Depending on what they say, you may find that they come off very differently than they want to.

If you had one wish right now, what would it be?

This question can give you a deeper understanding of a person’s priorities. Does their wish benefit themselves, their loved ones, or the world as a whole? Is it short-term or long-term? Whatever the answer, it can teach a lot about their current situation and future goals.

What fictional character are you most like?

Asking a person to compare themselves to a character in their favorite TV show, movie, or book can give you a simple way to learn a lot about them in a short period of time.

What does your ideal friend weekend look like?

Spending time with friends is important to many people, and knowing how they would spend a weekend with the ones they love can reveal the kinds of things they may wish the two of you to do together in the future. Learning their favorite game, movies, destinations, and other activities can help you determine whether you have common interests.

What is your best habit? What about your worst habit?

Learning what a person considers to be their best or favorite trait teaches you something about them while also telling you where their priorities lay. Similarly, knowing what they consider to be their worst habit can reveal where they believe they can improve themselves.

What is your deepest fear?

Knowing a person’s biggest fears can be important in any relationship, as it teaches you topics and behaviors you might avoid with that person. Additionally, many fears originate from previous experiences, so learning this information can give you insight into those details as well.

What is the most trouble you’ve ever been in?

Hearing how a person has gotten into trouble in the past – whether in childhood or as an adult – can reveal certain behaviors of a person while also giving you an opportunity to see whether or not they express remorse, depending on the situation they describe.

What is your most embarrassing moment?

Because these events are in the past, talking about embarrassing moments can often give you both something to laugh about and can strengthen a relationship. It can also show you the types of situations that a person finds embarrassing.

What is the craziest thing you’ve ever done for someone you love?

Love can drive people to extremes, but knowing just how far a person has gone – or the sacrifices they’ve made to make a partner, friend, or family member happy – can reveal the type of person they are to the people they love.

What is the most exciting adventure you’ve ever been on?

A person’s past adventures can help influence their future adventures. Whether they are an old friend or a new one, you might consider being a part of their adventures in the future, so knowing their preferences can be helpful.