60 "How Well Do You Know Me" Questions to Improve Your Relationships

"How well do you know me?" is a game you've probably played before with your friends, family members, or significant others. It's a simple activity that can be a great way to remind people how important they are to one another and even help them get to know one another better.

It often goes like this: One person asks a question of the other person or the group. These questions are centered around a specific aspects of a person's life, interests, or history. The depth of these questions often varies depending on the nature of the relationship, how long you've known each other, and how well you know each other.

According to Domenique Harrison MPH, LMFT, LPCC, known as The Racial Equity Therapist, such questions often come from a genuine desire for security, closeness, and connection. "While having curiosity about the lives of those close to you can come from a reflective and introspective place, some individuals may have an ulterior motive to test or stump their loved ones," she also notes.

Reasons to Ask "How Well Do You Know Me" Questions

The goal of "How well do you know me" questions is to help deepen the connection between people. By prompting the other person to answer such questions, people are encouraged to think about what they know about the person (as well as some of the things they don't know but might want to).

"These questions can come from two places, one healthy and one less so. Sometimes, these are playful quizzes, sort of like the old game show 'The Newlywed Game.' In fact, I have seen a version played on 'Married at First Sight.' In those cases, it’s a game, more about memory than about commitment, and it’s fun. Healthy!" says integrative therapist Renée Zavislak, MS, MA, LMFT.

In other cases, such questions may have a less well-intentioned side.

However, she also notes that this is an understandable thought process. Being seen is an important parts of attachment. Many times, these asking these questions stems from a desire to feel seen by our partners, she suggests.

Some other reasons you might opt to pose such questions include:

Authentic, Honest Communication

"How well do you know me" questions encourage people to be honest and open with one another. This can help improve communication and help people to discuss experiences, memories, thoughts, and feelings that might not otherwise come up in their day-to-day conversations.

"Such questions would be a fun and interactive way to check common knowledge and shared experience, which helps to develop connections among people," says Niloufar Esmaeilpour, MSc, RCC-ACS, a registered clinical counselor at Lotus Therapy & Counselling Centre. 

Forging Trust

Mutual self-disclosure plays an important role in any relationship, whether it's with your friends or your romantic partners. As you get to know one another better, there is a natural back-and-forth where each person reveals increasingly personal information about themselves.

As you share more information, you also start to establish a sense of trust and intimacy. You know each other better, so you also feel more comfortable sharing parts of yourself you might otherwise keep hidden.

Identifying Opportunities for Improvement and Growth

"How well do you know me" questions are also a great way to spot areas in your relationship that could use a little work. As you ask and answer these questions, you might find yourself thinking, "I can't believe they didn't know that about me!" or "How did I not know that about them?" 

The more questions you ask, the more you can see patterns and tendencies. For example, you might notice that while the other person knows much about your current experiences, they don't know much about your past. Or you might realize you've been holding back on sharing your thoughts and opinions. In either case, it's a great opportunity to see how you can improve.

Sometimes, these questions are less about seeing what the other person knows and more about giving you the opportunity to give an open and honest answer. They can provide a springboard for self-disclosure, which can help forge a closer, stronger, and more intimate connection between people.

"How Well Do You Know Me" Questions About Personal History

Questions that focus on your personal history are often best suited for people who have known you for a little while. Even if you didn’t know each other as kids, they’ve gotten to know you well enough and heard enough of your stories, so they have a pretty good chance of answering these questions with some accuracy.

• Who was my favorite teacher, and why did they leave such an impact on my life?
• What’s something that happened in my childhood that really affected who I am today?
• What was the silly nickname that my parents used to call me as a child?
• What did I like the most about my first job?
• What was my favorite thing about the place where I grew up?
• What was my favorite thing to do with my friends when I was a child?
• What things were the biggest challenges in my life during my childhood?
• Which of my family traditions would I like to continue in my own home?
• What hidden talent or skill did I develop when I was younger, and why is it still important to me today?
• What is my most cherished memory from my childhood that reveals something important about who I am now?
• What's the most unexpected or surprising thing you've ever learned about me?
• Did I have any dreams or aspirations when I was younger that I secretly still want to pursue?

"How Well Do You Know Me" Questions About Goals and Dreams

These questions are a great way to dig a little deeper and see how much the other person knows about your hopes and dreams. Such questions allow people to think deeply about your goals and learn a bit more about the sorts of things that motivate you. This can also be a great opportunity for you to find support and encouragement, which can further strengthen your bond.

• What is my single greatest aspiration in life?
• Can you list three things that are on my bucket list?
• Where would I go if I could visit any place in the world?
• Are there any things that you think I could learn how to do that would suit my interests and passions?
• If I had to change careers today, what would I want to do?
• If I could change anything about myself, what would it be?
• Have I ever talked about a dream that I gave up on? What were some reasons I decided to let that dream go?
• Can you think of a time when I faced a major setback? How did I handle it, and how did I move forward or overcome it?
• Do I have any fears, anxieties, or hesitations that keep me from achieving my goals?
• Do I have any childhood dreams that are still important to me today? Why do you think they are so long-lasting and significant to me?

"How Well Do You Know Me" Questions About Likes and Dislikes

Likes and dislikes are often the classic type of question people focus on when they ask “How well do you know me?” Instead of focusing on the basics like your favorite color, movie, or food, let’s dig a little deeper, shall we?

The following questions mine some of the same themes, but are designed to see how much the other person knows about the reasons behind your top faves and pet peeves.

• What is it about my favorite type of music that I enjoy the most?
• What was it that drew me to the career I have now, and would I choose it again if I had it to do over?
• What's a guilty pleasure of mine that I don't like to admit to enjoying? What is it about it I like so much (and why do I feel guilty for enjoying it)?
• Do I have any favorite songs, movies, or TV shows that are attached to some specific favorite memories of mine?
• What's something I dislike that always puts me in a bad mood?
• Have I ever mentioned a favorite place or activity that holds a special place in my heart?
• Are there any hobbies I would like to pursue if I just had the time?

"How Well Do You Know Me" Questions About Feelings and Fears

One of the hallmarks of a healthy relationship is the ability to be vulnerable and talk about what’s most important to you and what you fear most. The following questions focus on some of your innermost emotions, including your views of yourself and how you feel about the future.

• What do I want people to remember me for the most?
• If I could change anything that has happened in my life, what would it be?
• If you could be anyone else for one day, who would it be?
• What scares me the most about the future?
• If I could change anything about the world today, what would it be?
• What would I do with my day if I found out that I only had 24 hours left to live?
• Are there any situations where I struggle to control my emotions or how I express them?
• What's my biggest fear or insecurity, and what effect does it have on my life?
• Have I ever shared any recurring dreams or nightmares? What do you think those dreams say about my underlying feelings or fears?
• Is there any piece of media, such as song, movie, book, or work of art, that always evokes a strong emotional reaction whenever I experience it?
• What situations tend to make me feel the most vulnerable?
• Do I have any mantras or affirmations that help me feel secure, motivated, and encouraged?

"How Well Do You Know Me" Questions for Couples

Talking to your partner about what matters most to you in a relationship and how you see your future together can help bring you closer together. Having your partner ask such questions allows you to connect with them on a deeper level.

• What’s something about me that most people don't know?
• What did I think of you when I first met you?
• Where do I see us in five years?
• What do I like the most about myself?
• If I could spend money on anything, what would I buy?
• What is most important to me in a relationship?
• What’s my love language, and what effect does it have on how we relate to one another?
• What was my most embarrassing childhood memory?
• What's my favorite way to spend a lazy weekend day?
• What's my comfort food when I'm feeling down?
• Can you name a time in our relationship when I felt the closest to you? What made that moment so special?
• Has there ever been a time when I was surprised by something you did?
• What's something I've always wanted to know about you but have been afraid to ask?
• What's one thing about our relationship that I would change if I could?
• What do I consider to be the biggest red flag or dealbreaker in a relationship?
• What’s one of the less conventional traits or characteristics I find the most attractive about another person?
• Which actions and gestures help me to feel the most loved and appreciated?
• Are there any dreams or goals I've had to put on hold because of other priorities?
• What's a fear or insecurity of mine that affects how we communicate and connect as a couple?

Tips for Asking “How Well Do You Know Me” Questions

The great thing about "How well do you know me" questions is that they can be a comfortable way to initiate what can become a deep and meaningful conversation with another person. Research suggests that while they want to have these kinds of conversations, they often feel uncomfortable or unsure about how to initiate such discussions.

So what can you do to make sure that asking these questions feels safe and comfortable for everyone involved?

First, make sure that you pick the right time for a conversation. Some ideas include spending leisure time together or going on a date. It can also be a great way to pass the time during a car trip. The key is to choose a time and setting where you can focus on the conversation without a lot of distractions and where neither person feels stressed or pressured.

If someone else is asking you these questions, really pay attention to what you know about them, says Reena B. Patel, MA, LEP, BCBA, a psychologist and Licensed Educational Board-Certified Behavior Analyst. "The more you recall and show your partner or friend or coworker you remember their interests, the better it shows them how invested you are in the connection and relationship," she suggests.

Consider Your Own Reasons for Asking

Zavislak suggests that before you pose such questions, start by checking in with yourself to evaluate how you are feeling and assess your goals for asking such questions.

For example, if you are asking them because some aspect of your current relationship is triggering unresolved feelings from your past, you may be better off telling them what you want them to know rather than posing it as a quiz. Doing so allows you to express vulnerability and build greater intimacy with your partner without evoking defensiveness.

She also recommends modeling the behaviors you want, not what you get. If you want your partner to know more about you, start by asking them questions about themselves.

Takeaways

While it can be helpful and important to know the answers to some of these questions, knowing the exact answers is not an accurate indication of how well you know or how much you love your partner, and vice versa.

Many of these questions are fluid and the answers can change depending on a variety of factors. The answers can evolve as you evolve as individuals and in your relationship. The intention of "how well do you know me" questions can be to open up a dialogue, connect in a meaningful and intentional way, and asked from a place of playfulness and curiosity instead of judgment, criticism, or shame.

Instead of quizzing a partner or guessing if you don't know the answers, the questions can also be asked directly to deepen connection and intimacy.