100 Deep Questions to Ask Your Girlfriend—Grow Closer

How to use these questions

• Pick the right moment. Ask during a relaxed dinner, a walk, or a quiet evening—avoid launching deep talks when either of you is stressed.

• Start light, then go deep. Open with easier prompts and move into more personal topics as comfort grows.

• Listen and follow up. Ask a follow-up question or share a related memory—reciprocity is essential.

• Respect boundaries. If she hesitates, give space and don't pressure.

• Make it a ritual. Try a weekly “deep question night” or use a shared journal to record answers and reflections.

Childhood & Family (1–15)

1. What’s your favorite childhood memory, and why?

2. Who in your family shaped you the most?

3. What family tradition means the most to you?

4. What did you always want to be when you were a kid?

5. What’s a difficult moment from childhood you learned from?

6. Which childhood friend do you still think about?

7. What’s a smell or song that instantly brings you back to childhood?

8. Did you have a nickname—what’s the story?

9. What value did your parents teach you that you cherish?

10. What’s a small thing from your childhood you’d love to bring back?

11. What holiday memory sticks with you most?

12. How did your family celebrate achievements or milestones?

13. What was school like for you when you were young?

14. Who did you admire most when you were a teenager?

15. If you could revisit one birthday from your childhood, which would it be?

Dreams & Aspirations (16–30)

1. What’s something you want to accomplish in the next five years?

2. If money and time were unlimited, what would you pursue?

3. What’s a skill you’ve always wanted to learn?

4. How would your ideal day look in five years?

5. What legacy do you want to leave?

6. Is there a passion project you’ve shelved but would try again?

7. What would your dream home or life look like?

8. What fear is holding you back from a big dream?

9. If you could go back to school for any subject, what would it be?

10. What’s one bucket-list experience you want us to share?

11. Do you prefer a slow, stable path or bold, uncertain leaps?

12. What’s your proudest future aspiration?

13. How do you imagine your ideal retirement?

14. What small daily habit would transform your life?

15. If you had to choose a new career tomorrow, what would it be?

Love, Relationship & Values (31–45)

1. How do you define love?

2. What is your primary love language?

3. What’s the most meaningful way I can support you?

4. How do you feel most seen in our relationship?

5. What’s one thing you’d like us to do more often together?

6. What does commitment mean to you?

7. What relationship won’t you compromise on?

8. What’s a past relationship lesson you value most?

9. What scares you most about long-term commitment?

10. If we disagree, what’s the best way for us to resolve it?

11. What’s one small habit I do that makes you feel loved?

12. How do you want us to handle money and planning?

13. What role does family play in our relationship’s future?

14. What are your boundaries around privacy and independence?

15. What vision do you have for our life together in 10 years?

Worldview & Beliefs (46–60)

1. What belief changed the way you see the world?

2. If you could change one social issue, what would it be?

3. How do you decide what’s “right” for you morally?

4. What role does spirituality or religion play in your life?

5. How do you define success?

6. What assumptions about you would you like people to drop?

7. Who is someone you admire for their values and why?

8. How important is activism or volunteerism to you?

9. What cultural tradition do you hope to preserve?

10. Do you think people can genuinely change?

11. What’s your stance on forgiveness — unconditional or earned?

12. How does media shape your perspective?

13. What do you wish more people understood about mental health?

14. Do you believe in fate, free will, or both?

15. What ethical line would you never cross?

Emotional Life & Vulnerability (61–75)

1. What makes you feel most vulnerable?

2. How do you cope when you’re overwhelmed?

3. When do you feel most alive?

4. What emotion do you avoid and why?

5. When was the last time you cried, and what triggered it?

6. What do you fear losing the most?

7. What’s an insecurity you’re working on?

8. How do you want to be comforted when you’re sad?

9. What memory still makes you emotional?

10. How do you express anger, and what helps you calm down?

11. What does a safe relationship look like to you?

12. How do you build resilience after failure?

13. What compliment means more than any gift?

14. What do you do to feel re-centered?

15. What trust-building gesture matters most to you?

Future & Practical Planning (76–85)

1. Do you want children or not, and why?

2. How do you imagine balancing work and family?

3. What financial goals are important to you?

4. Would you rather travel or settle in one place?

5. How important is homeownership to you?

6. What traditions do you want for future holidays?

7. What’s your ideal approach to eldercare for parents?

8. Do you prefer to plan or be spontaneous about major life events?

9. How involved do you want extended family to be in our lives?

10. What would you want our funeral or memorial to be like?

Growth, Regret & Lessons (86–95)

1. What regret taught you the most?

2. Which failure are you most grateful for, and why?

3. What’s a habit you wish you’d started earlier?

4. Who do you wish you’d told something important to?

5. What lesson took you the longest to learn?

6. How do you decide when to let go?

7. What changes do you hope to see in yourself next year?

8. What book or idea changed you most?

9. What personal boundary was hardest to set?

10. How do you practice forgiveness toward yourself?

Playful & Intimate (96–100)

1. What small, silly thing always makes you laugh?

2. What’s one secret fantasy you feel comfortable sharing?

3. If we had one day with no responsibilities, what would we do?

4. Which song best describes our relationship, and why?

5. What is one memory of us you want to relive?

Final tips for asking (short)

• Use open follow-ups: “What made you feel that way?” or “Can you tell me more?”

• Keep a journal of answers (great for anniversaries).

• Revisit answers months later—people change, and so do answers.

Authority & Further Reading

• Gottman Institute—research on communication & relationships. https://www.gottman.com

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

• Greater Good Science Center (UC Berkeley)—science of connection. https://greatergood.berkeley.edu

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