100 Deep Questions to Ask Your Boyfriend

How to ask these questions

• Choose the right time: for example, relaxed evenings, walks, or a cozy weekend morning.

• Begin with simple exercises and gradually move on to more challenging ones. Start with easy exercises to warm up, and then move on to more difficult ones.

• Create safety: say, "You can ask me anything,” and be ready to say the same to others.

• Listen actively: repeat what you hear and ask more questions, like "What was that like?”

• Record answers: think about keeping a shared journal or doing a multimedia project so you can look back at your answers later.

Childhood & Family (1–15)

1. What is your most memorable moment from your childhood?

2. Who in your family influenced you the most, and why?

3. Which family tradition do you want to keep?

4. How did you get on with your parents when you were a child?

5. What fear did you overcome as a child?

6. Who was your first best friend, and what did you do together?

7. What hobby or skill were you surprisingly good at as a child?

8. What was your favorite family holiday, and why?

9. Did you have a nickname? How did you get it?

10. What lesson from childhood do you still follow today?

11. Which ancestor or relative do you feel closest to?

12. What was school like for you as a teenager?

13. What small tradition from your childhood do you want to recreate?

14. What's the funniest thing you remember from when you were a child?

15. If you could give your younger self one piece of advice, what would it be?

Dreams & Ambitions (16–30)

1. What is your biggest dream right now?

2. What do you want to have achieved in five years' time?

3. If you had no worries about money, what would you spend your days doing?

4. Which skill would you like to master?

5. Have you ever thought about starting your own business? What sort of business do you have in mind?

6. What would your ideal day look like?

7. Which small habit would make a big difference to your life if you kept doing it?

8. What are you afraid of?

9. What is one goal you would like us to achieve together?

10. If you could live anywhere, where would you live and why?

11. What do you want to be remembered for?

12. What's something you've always wanted to do?

13. What jobs might you consider changing to?

14. What does success look like to you?

15. What makes you want to get up in the morning?

Values & Beliefs (31–45)

1. What three things are the most important to you?

2. How do you decide what's "right" for you morally?

3. What would you fight for?

4. How important is spirituality or religion in your life?

5. What does integrity mean to you?

6. Do you think people can really change?

7. How important is money when we make life decisions?

8. Is it always best to be honest? Why or why not?

9. What do people think is true about you that you find surprising?

10. Which cultural tradition is most important to you?

11. Do you like to help other people? How?

12. What does forgiveness look like to you?

13. What are some things you used to believe that you no longer believe?

14. How do you balance being free and being responsible?

15. What problems with ethics do you have?

Relationship & Emotion (46–60)

1. What makes you feel most loved?

2. How do you like to receive support when you're stressed?

3. What can a partner do to make you feel safe?

4. How do you show someone you care?

5. What's your love language?

6. What kind of relationship habit would you like to develop with me?

7. How do you deal with conflict, and what helps you stay calm?

8. What do you wish I knew about your feelings?

9. What have you learned from past relationships?

10. Are you worried about making a long-term commitment?

11. How do you want us to celebrate important moments in your life?

12. What does 'trust' mean to you?

13. When are you most vulnerable, and how can I help?

14. How do you get over an argument?

15. What does a "healthy relationship" look like to you?

Vulnerability & Growth (61–75)

1. What are you still thinking about that you regret?

2. What failure made you a better person?

3. What are you working on to overcome your insecurities?

4. How do you deal with feeling sad or upset?

5. When was the last time you cried, and why?

6. What's something you've never told anyone?

7. How do you keep calm when you're under pressure?

8. What are you going to stop doing?

9. What habit do you want to start?

10. How do you take care of yourself?

11. What does mental health mean to you?

12. What mistake taught you the most humility?

13. How do you want to improve as a partner?

14. What makes you angry, and how can I help?

15. What is the most important boundary for you?

Big Picture & Practical Matters (76–88)

1. Do you want kids? If so, how do you imagine being a parent?

2. How should we work together on our finances?

3. Do you like city life, living in the suburbs, or living in the countryside?

4. What do you think we will be like in ten years?

5. How do you want to look after your parents?

6. What do you think about moving for new opportunities?

7. How much time do you need to yourself?

8. How do you want to celebrate major holidays?

9. How important is work to who you are?

10. How would you like to solve a big disagreement?

11. What legal and financial planning do you think is important for couples?

12. Would you ever take a big risk for your loved ones?

13. How do you make plans for the future while also enjoying life in the present?

Fun, Flirty & Random (89–100)

1. What little thing makes you laugh?

2. What's your favorite TV show or snack that you know you shouldn't be watching or eating?

3. If your life were a movie, which genre would it be?

4. Which superhero power would you choose, and why?

5. What's the most adventurous thing you've ever done?

6. If we could just take a spontaneous trip tomorrow, where would we go?

7. What's the most ridiculous nickname you've ever had?

8. What song always reminds you of us?

9. If you could spend one day with me, which day would you choose?

10. What would your dream anniversary celebration look like?

11. What's a silly habit you'll never give up?

12. What would be the best word to put on our future home's welcome mat?

Authority & Further Reading

• Gottman Institute: research into communication and relationships [https://www.gottman.com]

• APA (American Psychological Association)—relationships and mental health: [https://www.apa.org]

• Harvard Health Publishing has some great tips to help you feel your best. [https://www.health.harvard.edu]

Conclusion

1. Create a new project and give it a clear title (e.g., "100 Questions—Us").

2. Add a short description to explain what it is for.

3. Upload the questions and each answer as text entries. You can also attach photos, short voice notes, or videos to help explain what you mean.

4. Name your files in a descriptive way and use the category field on the platform to keep your projects organized.

5. You can share it privately or export it as printable cards or a slideshow to keep as a memory.