299 Deep Questions to Ask: A Guy, Girl, Friend, or Anyone

Want to get to know someone better? One way is to ask them deep questions. So here are some deep questions to ask different people—people like your relationship partner, friends, guys, girls, or whoever.

*This page may include affiliate links; that means I earn from qualifying purchases of products.

Maybe you're trying to get to know someone better. Maybe you're trying to make conversations more interesting. Or maybe, you just want to improve your communication skills by asking deep questions. In this article, we'll give you a bunch of deep questions to ask the different people in your life. We'll cover deep questions to ask a guy, a girl, your girlfriend, boyfriend or long-term partner, your friends, your best friend, and yourself.

Before we dive in, we thought you might first be interested in our well-being quiz. Take our quiz to get your free well-being report and resources.

And for our well-being entrepreneurs, coaches, and consultants? You can download our Wellness Business Growth eBook to get expert tips, tools, and resources to make a bigger impact and grow your wellness business fast.

Are You a Therapist, Coach, or Wellness Entrepreneur?

Grab Our Free eBook to Learn How to
Grow Your Wellness Business Exponentially!

✓ Save hundreds of hours of time ✓ Earn more $ faster
✓ Boost your credibility ✓ Deliver high-impact content

What Are Deep Questions to Ask and Why Do They Matter?

Communication may just be the backbone of healthy relationships. But communication is more than just a tool we use to explore ourselves. It can also be used to build closer bonds with others. One way we can do this is by asking deep questions—questions that lead others to self-disclose to us. This is how we get to know who the other person is for real.

In perhaps one of the best-known studies on relationships, Art Aron showed that when two people asked each other increasingly deep questions over a 45-minute period, they felt closer than two people who had just engaged in chit-chat (Aron et al., 1997). Further research suggests that when others self-disclose personal information, we like them more (Sprecher, Treger, & Wondra, 2013). This may partially explain why deep questions increase closeness.

Video: Deep Questions to Ask A Guy, Girl, or Friend

Do you prefer video? Then watch this video on deep questions which summarizes this article on deep quesitons.

Deep Questions to Ask Someone

To start increasing closeness (or just get to know someone), here are the questions you can ask anyone from Dr. Aron's study (Aron et al., 1997). They increase in intensity from the beginning to the end.

Deep Questions to Ask: Set I

Given the choice of anyone in the world, whom would you want as a dinner guest?
Would you like to be famous? In what way?
Before making a telephone call, do you ever rehearse what you are going to say? Why?
What would constitute a “perfect” day for you?
When did you last sing to yourself? To someone else?
If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?
Do you have a secret hunch about how you will die?
Name three things you and your partner appear to have in common.
For what in your life do you feel most grateful?
If you could change anything about the way you were raised, what would it be?
Take four minutes and tell your partner your life story in as much detail as possible.
If you could wake up tomorrow having gained any one quality or ability, what would it be?

Deep Questions to Ask: Set II

If a crystal ball could tell you the truth about yourself, your life, the future, or anything else, what would you want to know?
Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
What is the greatest accomplishment of your life?
What do you value most in a friendship?
What is your most treasured memory?
What is your most terrible memory?
If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
What does friendship mean to you?
What roles do love and affection play in your life?
Share something you consider to be a positive characteristic of your partner. Share a total of five items.
How close and warm is your family? Do you feel your childhood was happier than most other people’s?
How do you feel about your relationship with your mother?

Deep Questions to Ask: Set III

Make three true “we” statements each. For instance, “We are both in this room feeling…”
Complete this sentence: “I wish I had someone with whom I could share…”
If you were going to become a close friend with your partner, please share what would be important for them to know.
Tell your partner what you like about them; be very honest this time, saying things that you might not say to someone you’ve just met.
Share with your partner an embarrassing moment in your life.
When did you last cry in front of another person? By yourself?
Tell your partner something that you like about them [already].
What, if anything, is too serious to be joked about?
If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?
Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?
Of all the people in your family, whose death would you find most disturbing? Why?
Share a personal problem and ask your partner’s advice on how they might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.

Deep Questions to Ask a Girl

You can ask girls and guys many of the same deep questions (as listed above), but I thought it might be helpful to also provide some additional deep questions to ask a girl or guy. So here are some extra questions to ask a girl.

Do you want to have a baby? Why? (Or why did you have a baby?)
Have you ever been “mansplained,” and if so, what did you do about it?
How do you feel about the #MeToo movement?
Have you ever asked a guy out on a date?
How do you feel about the idea that some people think the female organism is a myth?
If you could choose, would you have chosen to be born a girl or guy?
What do you think it means to be a woman?
What's your favorite thing about being a woman?
What's your least favorite thing about being a woman?
How do you feel about how females are depicted in movies and TV?

Video: How to Ask Better Questions (Tips for Guys)

Deep Questions to Ask a Guy

Here are some extra deep questions to ask a guy:

Do you ever feel pressure to be the provider in your family or relationship?
What do you think about expressing your emotions?
How do you think about women?
How do you feel about being responsible for pushing a relationship forward (e.g., asking a girl on a date or to marry you?)
What do you think of society's idea of what a man should be?
What do you think the challenges are of being a man in the modern world?
How do you build friendships with other guys?
What is your definition of being a man?
What's your favorite thing about being a man?
What's your least favorite thing about being a man?

Deep Questions to Ask Your Partner (Boyfriend or Girlfriend)

When you're getting to know your relationship partner, there may be a number of deep questions to ask that can help you get closer to them and also understand them better. These questions may also help you determine whether they are a good fit for you in the long term.

What do you look for in a relationship?
What personal qualities do you love?
Do you believe in marriage? If so, what age do you think is the best for marriage?
Do you believe in soul mates?
What is your love language?
What is your idea of a perfect date?
What is your idea of a perfect vacation?
How do you describe commitment? How do you describe freedom?
Do you want to have kids?
How do you imagine your life in 10 years? 20 years? 50 years?
If you had all the money you needed, what would you do with your life?
Where would you put yourself on the workaholic to relaxaholic spectrum?
How do you react when you're upset?
If you had a partner who gained a lot of weight, would you stay with them?
What do you think leads people to cheat in relationships?
If you were having relationship troubles, would you ever go see a relationship counselor?
What's one time when you had to compromise? How did that feel to you?
What would be the perfect amount of time each day that you'd spend with your partner?
What’s a deal-breaker for you in a relationship?
What is a healthy relationship to you?

A Few More Deep Questions to Ask for Girls and Guys

Here are a few other good lists of deep questions to ask to get to know your romantic partner better:

Deep Questions to Ask Friends

Maybe you're looking to get to know your friends better. Here are some deep questions to ask your friends.

If you could magically change one thing in your life, what would it be?
What do you think of mindfulness?
Do you think we’d be better off without social media?
What do you think it means to be healthy?
What do you love the most in life?
Do you vote?
Do you believe in karma?
What do you think about freedom of speech?
Do you think there is an afterlife of any kind?
What do you think about veganism?
What do you think about the current younger generation?
Do you think bullies see themselves as bullies?
Do you tend to have trust issues?
Do you feel like men and women are equal?
Do you think people can change?
What's your favorite activity to do with friends?
What's one thing you believe in that's kinda weird?
Where is your favorite place to go eat?
What was one of your funniest moments?
If I asked you, "Who are you?" How would you answer?

Deep Questions to Ask Your Best Friend (Deep Personal Quesitons)

Sometimes there are those personal questions that you're just not comfortable asking anyone but your best friend. Here are a few of these extra-deep questions to only ask your best closest friends:

What do you like about me?
What are my best qualities?
What are my worst qualities?
What aspects of myself do I need to work on to be a better friend?
What makes you feel comfortable around me?
What do you think it is about us that made us such good friends?
Do you have any secrets that you need to get off your chest? If so, I promise to hold them with you.
Do you think we'll still be friends when we die?
What do you think your life would be like without me?
What's one thing you'd like to do together that we haven't yet done?

Deep Questions to Ask Yourself

Last but not least, you may want to ask yourself some deep questions to better get to know yourself. By asking ourselves deep questions we can uncover thoughts and beliefs we didn't even realize we had. So check out these deep questions to ask yourself get to know yourself better.

Do you respect yourself?
Are you confident? Why or why not?
Do you like who you are?
How do you express your emotions?
What makes you happy?
What are your strengths and weaknesses?
Do you forgive those who have hurt you? How?
Do you think you're brave? Why or why not?
How do you engage in self-care?
Do you try to grow and improve your abilities?
Are you proud of yourself?
Do you know what you want in life?
In what ways do you think positively? negatively?
What's your personal mission statement?
Do you believe you can manifest your dreams?
What are your long-term goals?
What are you thankful for?
Do you love yourself?
What are your core values?
Do you consider yourself an introvert, extrovert, or somewhere in the middle?
What motivates you?
How do you respond to rejection?
Do you ever feel shame or guilt? What causes it?
Do you suppress or express your emotions? Why and how?
Are you generally present in the moment or do you spend a lot of time in your head?
Do you have a healthy relationship with your smartphone?
What makes you feel vulnerable?
What are your good habits and bad habits?
What is your true calling?
What makes you feel empowered? Disempowered?
What anti-stress strategies help you most?
Do you ever have FOMO (Fear of Missing Out)?
Do you have an easy or hard time letting go of the past?
How do you self-soothe when you're upset?
Do you tend to have a scarcity mindset or an abundance mindset?
What's your communication style?
Do you practice random acts of kindness?
What is your best life?
What makes you jealous or envious?
Have you ever faked happiness?
How secure or insecure do you tend to be in relationships?
Do you tend to be an optimist or a pessimist?
How positive are you about your body?
Have you ever cheated emotionally?
What are your highest aspirations?
What negative thoughts do you have? How might you shift them to be more positive?
Have you ever been in a toxic relationship?
What makes you laugh?
How many hugs do you need each day?
What brings you the most joy?

Articles Related to Deep Questions

Here are some more articles that may help you build the skills that support healthy relationships and social bonds.

Books Related to Deep Questions

If you’d like to keep learning more about deep questions to ask, here are a few books that you might be interested in.

Final Thoughts on Deep Questions to Ask

Asking deep questions can be a great way to learn more about others, increase closeness between you, and have more interesting conversations. Hopefully, these lists of deep questions to ask gave you a good place to start.

Don't Forget to Grab Our Free eBook to Learn How to
Grow Your Wellness Business Exponentially!

References

Aron, A., Melinat, E., Aron, E. N., Vallone, R. D., & Bator, R. J. (1997). The experimental generation of interpersonal closeness: A procedure and some preliminary findings. Personality and social psychology bulletin, 23(4), 363-377.
Sprecher, S., Treger, S., & Wondra, J. D. (2013). Effects of self-disclosure role on liking, closeness, and other impressions in get-acquainted interactions. Journal of Social and Personal Relationships, 30(4), 497-514.

Are You a Therapist, Coach, or Wellness Entrepreneur?

Grab Our Free eBook to Learn How to Grow Your Wellness Business Fast!

Key Articles:

Content Packages: