100 Engaging Questions to Deepen Your Relationship

How to use these questions

• Choose the right time. The best times for this are when you are not being disturbed (e.g., when you are out for a walk, having dinner, or going to bed).

• Mix light and deep. Use playful and vulnerable prompts together to keep things balanced.

• Try to listen carefully. Think about what has been said, ask one question to check you understand, and don't interrupt.

• Respect personal limits. Offer to pass and be patient if your partner needs time.

• Write down the answers. Think about recording them in a shared journal or multimedia project.

Fun & Light (1–15)

1. What would your perfect weekend with me look like?

2. If you could have any superpower, what would it be?

3. Who was your celebrity crush when you were younger?

4. What's the silliest thing we've done together?

5. What is the one film that always makes you cry, whether you're happy or sad?

6. What's your favorite memory you've shared so far?

7. If we could fly anywhere tonight, where would we go?

8. What's the weirdest food you secretly love?

9. Which fictional couple do you like, and why?

10. Which karaoke song would you like to sing with me?

11. Do you prefer big adventures or cozy nights in?

12. What hobby would you like us to try together?

13. What was the best surprise you ever got?

14. If our life were a movie, what genre would it be?

15. What small, silly tradition do you think we should invent?

Childhood & Origins (16–30)

1. Which memory from your childhood do you think about the most?

2. Who was your biggest role model when you were a child?

3. Which tradition from your family do you want to keep?

4. When you were a child, what did you want to be when you grew up?

5. Which friend from your childhood would you like to get back in touch with?

6. What was your favorite holiday as a child?

7. Did you have a secret hideout or special place?

8. Which teacher had the biggest impact on you?

9. What was the funniest nickname you had when you were a child?

10. What small thing from your childhood do you miss?

11. What was the biggest fear you had when you were a child?

12. What things you learned as a child influenced your values as an adult?

13. Which family story makes you laugh?

14. Did you have a family recipe you really liked?

15. How did you feel about your home when you were growing up?

Values & Life View (31–45)

1. What three values do you look for when making decisions?

2. What makes a life meaningful?

3. How important is spirituality or faith in your life?

4. If you had more hours in the day, what issue would you spend your time on?

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

6. Do you think people can really change?

7. What things are important to you that you would never compromise on?

8. What kind of person do you want people to remember you as?

9. What is the point of being kind and understanding other people's feelings in public?

10. When do you feel most purposeful?

11. How do you handle moral dilemmas?

12. Which cultural tradition is most important to you?

13. What does having integrity look like in everyday life?

14. How do you balance looking after yourself with helping other people?

15. What do you want to be remembered for?

Relationship & Intimacy (46–65)

1. When did you first realize you loved me (or felt very close to me)?

2. What's one small thing that makes you feel loved?

3. How do you prefer to get support when you're stressed?

4. What's the most important relationship habit you have?

5. What do you think about people showing their love in public?

6. What things are non-negotiable for you in a partnership?

7. How do you like to celebrate anniversaries?

8. What can I do to help you feel safer or more secure?

9. How do you want us to deal with any problems?

10. What is a memory of us that always makes you happy?

11. How important is it to be independent in a relationship?

12. Which relationship tradition would you like to start?

13. How do you know when to forgive someone and move on?

14. What makes you think someone is committed?

15. What do you think we will be like in five years?

16. How important is trust in your day-to-day life?

17. What's one romantic thing you've never said but want to?

18. What do you want to happen between you and us?

19. What do you like to do when you want to catch up with people after a busy day?

20. What makes you feel listened to and valued?

Personal Growth & Challenges (66–80)

1. What mistakes have you made that taught you something important?

2. Which fear do you want to overcome this year?

3. What would be the best thing for you to do regularly to improve your life?

4. How do you recharge when you're tired?

5. What boundaries have you learned to set?

6. When did you feel most proud of yourself?

7. What have you learned from your mistakes?

8. How do you forgive yourself and others?

9. What change would you like to see in your life next year?

10. How do you measure personal success?

11. Which activities do you think are best for your mental well-being?

12. What choice did you make that taught you the most?

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

14. What book or idea changed your life?

15. What small ritual do you do every day?

Future & Practical (81–90)

1. Do you want children or not? Why?

2. How do you want to manage your money together as a couple?

3. City life, suburbs, or countryside—which and why?

4. What kind of trip do you want to go on?

5. What do you want to achieve in your career?

6. How much time do you need to spend on your own each week?

7. What kind of tradition would you like to start with your family?

8. What do you think retirement will be like?

9. What causes would you leave a legacy to?

10. Which household routine could help us all to feel better?

Playful, Silly & Deep Curiosities (91–100)

1. If you had to pick one song as our anthem, what would it be?

2. What small, silly fear do you still have?

3. If you could relive one day of our life together, which day would you choose?

4. What would your perfect day without phones with me look like?

5. If you could choose, which made-up world would you live in for a month?

6. What's the funniest thing about me that you don't tell anyone?

7. If you could instantly become an expert in one skill, what would it be?

8. What is the one question you would like me to ask more often?

9. If you could teleport us anywhere tonight, where would we go?

10. What one simple habit should we keep forever?

Why these questions work (authority & evidence)

Use Tellsomething to turn conversations into multimedia keepsakes.

1. Create a project with a clear title (e.g., "100 Questions—Our Story");

2. Add a short description and category;

3. Upload question-answer pairs as text entries and attach photos or 15–60 second video clips for context.

4. Use descriptive file names and the project category to organise;

5. Share privately, export a printable journal, or gift the finished product.