220+ Best “How Well Do You Know Me?” Questions for Friends

Want to know if your BFF, bae, or fam has been paying attention? They probably know a lot about you, but we'd bet there are still a few facts that would surprise them! Asking them questions about yourself is a fun way to quiz them on how well they know you, including your likes, dislikes, dreams, and fears. We spoke with relationship experts to get their best tips on asking good questions and having great conversations with the people close to you, including your friends, best friends, and family. Keep reading to see how well your loved ones know you!

Top “How Well Do You Know Me?” Questions

Do I believe in fate or free will?
What’s my goofiest dance move?
If I could found a country, what would I name it?
Do I believe in soulmates?
What is my biggest pet peeve?

Section 1 of 14:

Juicy “How Well Do You Know Me?” Questions for Best Friends

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See if your best friend knows you on a deeper level with juicy questions. No plans? No problem! Whip out a variety of juicy, get-to-know-you questions with your bestie and see where the conversation goes. Chances are, you'll both learn something new about one another!
- Do I have a nemesis?
- Have I ever shoplifted anything?
- What’s the craziest thing I’ve ever done?
- Have I ever lied about my age?
- What’s the biggest thing I’ve ever gotten away with?
- Do I care more about appearance or personality?
- Do I believe in fate or free will?
- What’s my biggest regret in life?
- Am I a planner, or am I more spontaneous?
- Would I say I’m an introvert or an extrovert?
- Have I ever gotten into trouble with the police?
- What’s my toxic trait?
- Have I ever been caught in a big lie?
- Have I ever spread a rumor about someone?
- What are my hidden talents?
- What has been my most embarrassing moment?
- Do I have any allergies?

Section 2 of 14:

Funny “How Well Do You Know Me?” Questions for Friends

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Ask your friends funny questions about yourself to lighten the mood. Sure, your pals may know all the tea in your personal life—but how well do they really know you? “Make sure that the time you spend together feels rich in terms of the conversation,” recommends licensed clinical psychologist Chloe Carmichael, PhD.^{[1]
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Expert Source

Chloe Carmichael, PhD
Licensed Clinical Psychologist

Expert Interview} Toss around a few of these interesting questions to connect with each other:
- Would I rather have hands for feet, or feet for hands?
- What’s the strangest thing I’ve seen someone do in public?
- What’s my goofiest dance move?
- What is the easiest way to make me laugh?
- What’s the most embarrassing song on my playlist?
- Would I rather be bald or have no eyebrows?
- What’s the best excuse I’ve ever given to skip work or school?
- What celebrity would I challenge to a duel?
- What’s my unlucky number?
- What’s the dumbest thing I’ve done while drunk?
- Who do I think is the most attractive animated character?
- If I had a warning label, what would it say?
- What movie title best describes my life?
- If I were a character in a sitcom, who would I want to be and why?
- Do I think a hot dog is a sandwich?
- What’s my favorite corny joke?
- Who is my celebrity crush?

Section 3 of 14:

Random “How Well Do You Know Me?” Questions for New Friends

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Help new friends get to know you better by quizzing them about yourself. Dr. Carmichael defines a friend as “somebody who's reliable, somebody you can count on, somebody who genuinely celebrates when things go well in your life.”^{[2]
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Expert Source

Chloe Carmichael, PhD
Licensed Clinical Psychologist

Expert Interview} Build that trust and get to know each other better with some of these “How well do you know me?” questions:
- How long would I survive the zombie apocalypse?
- Who do I think should play me in a movie about my life?
- If I could be any animal, what would I be and why?
- What kind of secret society would I start?
- If I could jump into a pool of anything, what would it be?
- What do I do when nobody is watching?
- Have I ever eaten a bug?
- When was the last time I sang to myself?
- If I could found a country, what would I name it?
- When is my birthday?
- What size shoe do I wear?
- What is my middle name?
- What's my star sign?
- If I were an animal, what animal would I be?
- If I had a time machine, what time would I visit and why?
- Would I rather live in the heart of a bustling city or out in the secluded country?
- Am I a morning person or a night owl?

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Deep “How Well Do You Know Me?” Questions for Couples

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Strengthen your bond with your sweetie by asking deep questions. No matter how well you know your partner (or how well you think they know you), there's always something new that you can learn. Break the ice and take an even deeper dive as you discover more about your partner with these questions:
- What's something that always cheers me up when I'm sad?
- What is my biggest insecurity?
- Do I like talking on the phone, texting, or chatting in person more?
- If I had the choice to become immortal, would I do it?
- If I could bring anyone back to life, who would it be?
- What is my biggest fear?
- What is my biggest secret?
- What do I like most about you?
- Do I believe that unconditional love is real?
- Do I believe in soulmates?
- When do I feel closest to you?
- Why do I love you?
- If I could relive one day in our relationship, what would it be?
- What do I fear most in our relationship?
- How did my last relationship end?
- How do I define cheating?
- What are my parents’ names?

Section 5 of 14:

“How Well Do You Know Me?” Questions for Family

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Connect with a family member by quizzing them on your life. Sometimes, you’re close to family members, but they don’t know you as well as your friends do. Bridge that gap in a fun and interesting way by asking them a few “How well do you know me?” questions:
- Would I rather live by the ocean or in the mountains?
- What is my favorite family tradition?
- What do I think our family theme song should be?
- What’s my favorite story about someone in our family?
- What one word would I use to describe our family?
- Do I like my middle name?
- What is my favorite thing to collect?
- What is my favorite thing to do on the weekends?
- What do I think is the best piece of advice I’ve ever received?
- Which family member would I trust to follow me around and narrate my life?
- Do I think money can buy happiness?
- Who in the family am I the most honest with?
- Who in the family do I think I’m most like?
- What is my favorite family memory?
- Who do I think is the funniest person in our family?
- What are my plants’ names?
- If I could meet one historical figure, who would it be?

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“How Well Do You Know Me?” Questions about Likes & Dislikes

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Cover the basics with questions about your likes and dislikes. According to clinical psychologist Allison Broennimann, PhD, “It's hard to have a nourishing friendship without taking the time to build it.”^{[3]
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Expert Source

Allison Broennimann, PhD
Clinical Psychologist

Expert Interview} Start making a connection with your friends by asking questions about how well they know your likes and dislikes, like the ones below:
- Do I prefer sweats or dressing up?
- What movie do I hate that everyone else loves?
- Do I prefer to stay in or go out on the weekend?
- What’s my least favorite type of music?
- Do I prefer sunny or rainy days?
- What’s the worst book I’ve read all the way through?
- What’s my least favorite emotion?
- What luxury item would I splurge on?
- What is my biggest pet peeve?
- What's my favorite smell?
- Do I like talking on the phone, texting, or chatting in person more?
- Am I a dog or a cat person?
- What is my favorite song or artist?
- What's my favorite TV show?
- What's my favorite podcast?
- What is my favorite sport to play?
- What is my favorite movie?

Section 7 of 14:

“How Well Do You Know Me?” Questions about Food

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Ease into deeper questions with easy ones about food. The kinds of food you like—or don’t like—are a great way to start a conversation. While they may seem more superficial, these questions can lead to good conversations that get you warmed up for tackling deeper subjects:
- What do I think is the best food for a food fight?
- What kind of food would I take a bath in?
- How often do I skip breakfast?
- Do I prefer local or imported produce?
- How spicy do I like my food?
- What is my go-to midnight snack?
- How often do I eat out in a week?
- What’s the grossest food I’ve ever eaten?
- What’s my favorite topping for pizza?
- What’s my favorite comfort food?
- What’s the strangest food combination I’ve ever eaten?
- Do I prefer dark, milk, or white chocolate?
- What food do I hate?
- Do I prefer sweet or savory foods?
- What is my favorite restaurant?
- What is my favorite type of potato?
- What's my favorite ice cream flavor?

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“How Well Do You Know Me?” Questions about Travel

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Share your worldviews with travel-related questions. Talking about your travel bucket list or dream vacation can reveal how you see yourself… and how well your friend understands you.^{[4]
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Research source} Use these questions about travel to share more about yourself with your friend in a fun and interesting way:
- Do I think a luxury destination is worth the money?
- Which historical sight has moved me the most?
- What has been my most luxurious travel experience?
- What culture has had the biggest impact on me after travel?
- Am I willing to go to a place that isn’t completely safe?
- What do I think is the most overrated place I’ve ever traveled to?
- Do I consider myself a thrill-seeker?
- How much research do I do on a destination before I travel there?
- Do I prefer staying in a hotel or in an Airbnb?
- What do I enjoy doing during long flights?
- Do I like organized tours or wandering around?
- How long is my ideal vacation?
- Do I like to travel solo or with others?
- What is my favorite place I’ve ever visited?
- What surprised me the most about my last trip?
- What would be my dream vacation?
- If I could travel anywhere, where would I go?

Section 9 of 14:

“How Well Do You Know Me?” Questions about Childhood

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Dig into your childhood to see if they know your inner self. Your childhood experiences have a huge impact on your life and how you think about the world.^{[5]
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Research source} Ask someone these questions about yourself to give them a better sense of how your childhood has shaped who you are as a person:
- How many times did I move when I was a kid?
- What was the worst punishment my parents gave me when I was younger?
- What was my favorite subject in school?
- What is my first memory?
- Did I have a childhood nickname?
- Who was my first crush?
- What’s the first book I remember reading?
- What did I want to be when I grew up?
- What kind of student was I in grade school?
- What’s something I wish someone had taught me when I was younger?
- Were you ever bullied as a child?
- What’s the biggest secret I kept from my parents when I was a kid?
- How old was I when my parents told me about the birds and the bees?
- Who was my childhood hero?
- What is one of my best childhood memories?
- What pets did I have as a child?
- Who was my favorite teacher growing up?

Section 10 of 14:

“How Well Do You Know Me?” Questions about Relationships & Love

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Ask questions about your philosophy on dating and relationships. Your friends have the power to influence your romantic relationships.^{[6]
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Research source} So, it’s important for them to have a good understanding of what you want. Ask these “How well do you know me?” questions about love and relationships to see if they truly understand what you really want in your love life:
- Have I ever had a crush on my sibling’s friend?
- Do I think I’m a good kisser?
- Have I ever played dumb to get someone’s attention?
- Have I ever been in a love triangle?
- Have I ever tried to sabotage someone else’s relationship?
- Have I ever sent a sexy text to the wrong person?
- Have I ever friend-zoned anyone?
- Do I believe in love at first sight?
- What is my love language?
- Have I ever ditched a date?
- Have I ever cheated on anyone?
- Would I rather be single or in a relationship?
- Have I ever dated someone I met online?
- What’s my go-to move to get someone’s attention?
- What’s the most awkward date I’ve ever been on?
- What do I think is the most attractive physical feature?
- When did I have my first kiss?

Section 11 of 14:

“How Well Do You Know Me?” Questions about Career & Goals

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Test your loved ones on your professional goals and work life. Good friends are like your personal cheerleaders who are there to encourage you and celebrate your achievements. Ask them these questions about yourself to make sure they know about your life goals and what you want to do in your career:
- Do I go to work when I’m sick?
- What motivates me to go after my goals?
- What is the most rewarding part of my job?
- What’s the best thing I’ve ever achieved in the workplace?
- If I could have any other career, what would it be?
- How did I end up in my current job?
- What job do I think I’d be terrible at?
- What is my definition of success?
- What is my biggest career goal?
- What was my first job?
- Have I ever been fired from a job?
- What’s my favorite way to celebrate my professional accomplishments?
- What’s my favorite work experience?
- Where do I see myself in 5 years?
- What’s my dream job?
- What does my ideal life look like?
- Would I rather be an astronaut or a deep-sea diver?

Section 12 of 14:

“How Well Do You Know Me?” Questions about Values

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Ask thought-provoking questions to reveal your personal values. You don’t have to have the same values and beliefs to have a rewarding friendship. According to licensed marriage and family therapist Lia Huynh, LMFT, “There is so much to like and enjoy about a person aside from your faith [and] beliefs.”^{[7]
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Expert Source

Lia Huynh, LMFT
Licensed Marriage & Family Therapist

Expert Interview} But asking them questions about yourself, like the ones below, can help them understand how you look at the world:
- What do I believe my purpose in life is?
- Would I convert to a different religion for a life partner?
- What is the most awe-inspiring thing I’ve ever seen or experienced?
- Do I feel like I know what’s right and wrong?
- What do I think is the worst quality a person can have?
- What are the most important values I’ve always stood by?
- What do I think my spirit animal should be?
- What’s the biggest leap of faith I’ve ever taken?
- What’s my life motto or mantra?
- If I could ask God one question, what would it be?
- What’s a value I’m unwilling to compromise on?
- Have I ever participated in a protest?
- Do I think people are basically good or basically bad?
- What do I believe happens when we die?
- Do I believe in God or a higher power?
- If I could solve one problem in the world, what would it be?
- Do I consider myself religious?

Section 13 of 14:

“How Well Do You Know Me?” Questions about Friendship

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Share what you want in a friend by asking questions about friendship. Not everyone thinks of friendship in the same way. These differences can cause conflicts if you don’t understand what the other person expects from friends. Use these questions about yourself to see if you and your friend are on the same page in your friendship:
- How long has my oldest friend been in my life?
- What’s my favorite memory of our friendship?
- How do I want to be comforted when I’m upset?
- Am I still in touch with any of my childhood friends?
- What does my ideal friend’s weekend look like?
- Do I think friends or family are more important?
- What do I value most in a friend?
- Do I believe in having one best friend?
- What do I think it means to be a good friend?
- What was my impression of you when we first met?
- What recent experience do I think has brought us closer together?
- What do I think is more important in a friendship, loyalty or honesty?
- Is there anything I would change about our friendship?
- When have I felt most betrayed by a friend?
- Have I ever broken up with a friend?
- What’s something I consider unforgivable?
- How did we meet?

Section 14 of 14:

Asking Questions to Connect with Others

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Create a safe space for the other person to make mistakes. It can be disappointing when someone gets an answer wrong, but don’t let it get to you. And, above all, don’t get mad at them for not getting it right. Dr. Carmichael explains, “A big part of friendship is feeling supportive of each other.”^{[8]
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Expert Source

Chloe Carmichael, PhD
Licensed Clinical Psychologist

Expert Interview} That means not taking a wrong answer to heart.
- Asking “How well do you know me?” questions should be about having fun and getting to know each other better.
- Use it as an opportunity to have a conversation and tell them things about you they don’t already know, not as a “gotcha” moment.
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Ask follow-up questions to get a better understanding of their answers. “If you're truly present and curious in a conversation with anyone, then the next question that you ask will undoubtedly be meaningful,” suggests certified leadership & life coach Christina Stathopoulos, PCC, ACCC.^{[9]
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Expert Source

Christina Stathopoulos, PCC, ACCC
Certified Leadership & Life Coach

Expert Interview}
- Instead of hopping from question to question, dive deeper into your friend or family member’s answers by asking great questions that can’t be answered with a yes or no.
- Ask them to tell you why they answered the way they did. And if they give a wrong answer, tell them what the real answer is and why.
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Practice active listening to show you’re interested in what they say. “It's always very important to show curiosity and listen actively because a lot of people just want to be heard,” certified life coach Kirin Dejonckheere explains.^{[10]
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Expert Source

Kirin Dejonckheere
Certified Life Coach

Expert Interview} Dr. Carmichael also recommends that you show your friend that you value them by thanking them for being open with you.^{[11]
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Expert Source

Chloe Carmichael, PhD
Licensed Clinical Psychologist

Expert Interview}
- Listening carefully when you talk to a friend or family member also shows them you want to get closer and build your friendship.
- Active listening skills include limiting distractions, giving them your full attention, avoiding interrupting them, making eye contact, and occasionally nodding as they speak.
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Encourage the other person to ask you questions, too. “Another big marker of friendship is trust and intimacy, and really feeling known and seen by the other person. And so for some people, that means that they want to share some of the more personal, sensitive information about themselves,” says Dr. Carmichael.^{[12]
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Expert Source

Chloe Carmichael, PhD
Licensed Clinical Psychologist

Expert Interview}
- Being vulnerable and opening up can feel scary because you don’t know how the other person will react.
- But opening up to your friends can lead to better conversations that bring you closer together.