Many of us desire our partner or close friends to know us deeply and intimately. When your partner or best friend knows you - from surface-level likes and dislikes to vulnerable insecurities - it makes you feel seen and connected. Understanding one another on a deeper level nourishes long-lasting relationships. 

The following ‘How well do you know me questions’ are a fun way to connect and learn more about each other. These questions show areas where your partner or friends know you well and other areas of life that haven’t been talked about as much. 

As such, these questions allow you to share your story and strengthen your relationships. And, when you create space for your partner or friend to ask the question back, it helps you learn more about them and yourself. 

How to Create a Safe Space for Questions 

Before diving into the questions, create a safe space for a meaningful conversation to unfold. You don’t want to ask these questions when you’re both busy, distracted, or stressed. 

Rather, you want to carve out a time when you can be present and intentional with each other. Perhaps it’s a cozy date night with your partner or on a walk with your best friend. It can even be a good way to pass the time on a road trip. Or maybe it’s another form of communication, like the Waffle app. 

Waffle is a private platform for shared journaling. It’s a creative resource for couples, friends, and family members to know each other better. Using the app, you can ask your partner or friend group a ‘How well do you know me question,’ and they can respond when it’s most convenient. 

For example, Brooklyn uses Waffle with her long-distance best friend and says:

It has enabled us to continue sharing things we wouldn't normally remember, certain mundane details I wouldn’t bother sending in a text, but things I would definitely tell my best friend when I saw her every day!

Encourage Healthy Conversations

While it can be fun to “test” our partners or friends to see how well they know us, it’s important to start the conversation from a healthy place. If you feel like you’re trying to prove something or feel tension/stress before asking these questions, take a pause. During that pause, check in with yourself and see if it’s a time to be more direct with your feelings rather than asking questions.

Don’t expect your best friend or significant other to know all the answers or always answer them correctly. Remember, these questions are meant to support your relationship and deepen your connection. Start the conversation from a place of open curiosity, presence, and compassion. If hurt feelings come up, honor them, and take a step back from the questions if necessary.

Sometimes these types of conversations are hard to have in person. The Waffle app is a great way to ask your friends and partner deep questions in a safe space. Because it’s in a journal rather than a direct conversation, the other person can take time to process the question and think through their response.

Alisha shares:

It allows us to write out our feelings, and the other person can read and understand what is said and felt. We have trouble communicating how we feel sometimes without the other person being defensive or without it being taken the wrong way. Journaling on Waffle helps with this.

Make it Fun 

The best way to ask ‘How well do you know me questions’ is in a fun and playful way. Plan it as a game for a date or when you have your friends over. You can write down your favorite questions, place them in a jar and bowl, and take turns asking questions. That way, there’s a good mix of questions and you don’t have to pick which one to ask next. 

Okay, enough talk - check out the following questions to ask your partner or during a friend hangout. There’s everything from casual conversation starters to intimate and vulnerable questions for those closest to you. 

Casual How Well Do You Know Me Questions 

These icebreaker questions will help warm up the conversation before it moves to deeper territory. Try these conversation starters with your partner or on a group night with friends.  

1. Who’s my favorite band or musical artist? 

2. What’s my favorite movie and why? 

3. What are some of my hobbies? 

4. Have I ever broken a bone? If I have, how did I break it? 

5. How many siblings do I have? 

6. What’s my favorite book and why? 

7. What’s my favorite color? 

8. What’s my favorite song right now? 

9. Am I an introvert or extravert? 

10. What is my comfort food? 

11. What is my favorite animal? 

12. What are three things on my bucket list? 

13. If I could only watch one TV show for the rest of my life, what would it be? 

14. Who is my celebrity crush? 

15. What is my favorite sport? 

16. What is my zodiac sign? 

17. What is my biggest pet peeve? 

18. What is my favorite form of exercise? 

19. What is my favorite holiday?

20. What is my middle name? 

21. What’s my favorite thing to do in my free time? 

22. What’s my favorite ice cream flavor? 

23. What is my favorite food? 

Fun and Creative How Well Do You Know Me Questions 

The following fun questions will spark your partner's or friend's imagination. These are the types of questions that may have surprising answers or even lead to deep belly laughs. They will also help you learn more about yourself and the other. 

1. If I could be any animal, what would I be? 

2. If I could travel back in time, what decade or historical event would I travel to? 

3. If I were a dog, what breed would I be? 

4. What superpower do I wish I had?

5. If I could be any famous person, living or dead, who would I want to be and why?

6. If we lived in a magical place, what fairytale creature or being would I be?  

7. What fictional world would I love to visit? 

8. What is the quirkiest thing I do? 

9. If I could only eat one type of food for the rest of my life, what would it be? 

10. What makes me laugh? 

11. If I went viral on social media, what would it be for? 

12. What is the weirdest food craving I’ve had? 

13. What is my favorite outdoor activity? 

14. Do I believe in any crazy conspiracy theories? 

15. Do I prefer mountains, forests, the desert, or the beach?

16. What color describes my personality and why? 

17. What Hogwarts house am I? 

18. What is my favorite possession(s)?

19. If my life was a movie, what genre would it be? 

20. Do I like pineapple on my pizza? 

Deep How Well Do You Know Me Questions 

These questions will help create emotional intimacy, and show you the areas where your partner or loved ones truly see you. For questions they don’t know the answer to, it creates an opportunity to talk about these deeper areas of your life. 

1. What is something hardly anyone knows about me? 

2. Am I spiritual or religious? 

3. What brings me joy? 

4. What am I passionate about? 

5. What makes me feel comfortable and relaxed? 

6. What is my biggest fear? 

7. What are some of my insecurities? 

8. What makes me feel inspired? 

9. Where do I feel most at peace? 

10. What is a challenge I’ve had to overcome? 

11. What are my strengths or natural gifts? 

12. What makes me feel alive? 

13. How do I handle difficult experiences? 

14. What are my self-care habits? 

15. Which family member am I closest to? 

16. What are my goals for this year? 

17. Who do I look up to?  

18. What is my dream job? 

19. What is one of my unconventional or “out there” beliefs? 

20. What are my biggest dreams or aspirations? 

21. Do I have a close relationship with my family members? 

How Well Do You Know Me Questions for Couples 

Cozy up together for an evening in and see how well your partner knows you. Some questions may lead to beautiful conversations about your future, romantic needs, and relationship expectations. 

1. What is my favorite way to spend a relaxing evening? 

2. What is my love language? 

3. What do I deeply long for in a relationship? 

4. Do I prefer spontaneous adventures or planned vacations? 

5. In what ways have I grown since we first met? 

6. What does my ideal date night look like? 

7. Would I rather stay in or go out? 

8. What funny or quirky things do I do when I think no one is around? 

9. In what ways do I show my love for you? 

10. What do I love most about you? 

11. What is my favorite memory from our first date? 

12. What is one of my vulnerabilities? 

13. Do I want kids? 

14. What emotion do I feel or express the most? 

15. What do I envision for this relationship? 

16. Where is my favorite place to go when I feel sad or stressed? 

17. How do I feel about physical affection? 

18. Who is my best friend? 

19. What is something I want us to do more often? 

20. What is a dealbreaker for me in a relationship? 

21. What traits do I have that hold me back from shining my light? 

22. What do I value most in a relationship? 

23. How do I like my coffee? 

24. What is my go-to dinner recipe? 

How Well Do You Know Me in The Bedroom? 

These questions will help clarify sexual desires and boundaries. Be ready - they’ll bring some pleasurable heat to the conversation and may set the mood for intimate relations. 

1. Do I have any kinks? 

2. Do I prefer to be submissive or dominate?

3. What turns me on? 

4. What turns me off? 

5. What is my favorite position? 

6. How do I like to set the mood? 

7. Do I have any sexual fantasies? 

8. What makes me feel safe and cared for? 

9. What are my boundaries? 

10. How do I feel about sex toys? 

11. What’s my favorite way to be touched? 

How Well Do You Know My Past? 

While the past doesn’t define us, it does shape the person we are today. Ask your partner or friends these questions about your past to see how well they know your history. 

1. What is my favorite childhood memory? 

2. What was my first pet? 

3. Did I have any imaginary friends? 

4. What was my favorite thing to play with when I was a kid? 

5. What was my first job? 

6. What was my favorite class in high school? 

7. Who was my childhood best friend? 

8. What was my longest relationship? 

9. What was one of my childhood insecurities? 

10. Did I play any sports? 

11. What did I want to be when I grew up? 

12. What was my favorite thing to do as a kid? 

13. What was one thing that significantly impacted me from my childhood? 

14. When was my first kiss? 

15. What was the weirdest thing I believed as a kid? 

How Well Do You Know Me Travel Questions

Traveling is a significant part of many people's lives, making it a great way to spark conversation and share more about yourself. From inspiring travel memories to dreams of future destinations, see how well the people in your life know your travel history and plans. 

1. Have I traveled outside of the country? 

2. How many countries have I traveled to? 

3. What’s my favorite travel memory? 

4. Where’s my dream travel destination? 

5. What was the worst travel experience I’ve had? 

6. How do I pass the time on an airplane? 

7. Is there a trip that changed me as a person? 

8. What’s my favorite thing about road trips? 

9. Do I pack light, overpack, or always bring exactly what I need? 

10. Am I scared of flying? 

11. Would I rather go to a resort or stay in a local Airbnb? 

Self-Reflect

After reading or asking these questions, you may find that you don’t know every answer. For example, you may not know what makes you feel alive or what your goals are for this year. 

These questions are beautiful journal prompts that can lead you on a journey of self-discovery. When we truly know ourselves, we can authentically show up for others and create deep, lasting bonds. 

Even though the Waffle App is commonly used for couples and friends, you can also use it just for yourself. 

Waffle user Nate uses the app for himself, his friends, and his family. He shares:

I use Waffle mostly as a personal journal. Waffle has provided a space for my thoughts as I’ve gone through some tough moments in my life.

Improve Your Relationships with Waffle

Whether you use it for yourself or with others, the Waffle app will help strengthen and improve your relationships. And with the daily questions Waffle provides, you’ll never run out of things to talk about or reflect upon. Download the Waffle App today and start journaling with those you love most.