95 Meaningful Questions to Get to Know Someone—Deep & Fun

Quick tips before you ask

• Pick the right moment. Relaxed settings (walks, coffees, dinners) work best.

• Start light. Ease into deeper questions after rapport builds.

• Practice active listening. Reflect, follow up, and share your own answers too.

• Respect boundaries. If someone pauses or declines, offer space.

• Make it a ritual. Weekly question nights or a shared journal keep things consistent.

Light Starters (1–20)—great for first meets or warmups

1. What’s one small thing that made you smile this week?

2. Coffee or tea?

3. What’s your favorite comfort food?

4. Books or movies?

5. What hobby would you try if you had a free afternoon?

6. Beach day or mountain hike?

7. What show are you currently bingeing?

8. Do you prefer sunrise or sunset?

9. What’s the last photo you took?

10. What’s your go-to weekend activity?

11. What was your first job?

12. What’s your favorite season, and why?

13. Who is someone you admire?

14. What app do you use most?

15. What’s the best meal you’ve ever had?

16. Do you have a favorite local spot?

17. Are you an early bird or a night owl?

18. Do you collect anything?

19. What song do you always play on repeat?

20. One place you’d love to visit next?

Personal & Values (21–40)—builds empathy & alignment

1. What three words describe you best?

2. What value matters most to you in friendships?

3. What does “success” mean to you?

4. What’s a belief you’ll defend?

5. How do you like to spend a meaningful holiday?

6. What causes are important to you?

7. What quality do you most appreciate in others?

8. How do you prefer to receive support?

9. What cultural tradition do you cherish?

10. What role does spirituality or faith play for you?

11. What personal boundary is non-negotiable?

12. What does work–life balance look like for you?

13. How do you define a “good day”?

14. What habit improves your life most?

15. Are you driven more by passion or security?

16. What ethical line would you never cross?

17. How do you handle disappointment?

18. What does forgiveness mean to you?

19. What legacy do you hope to leave?

20. What value do you want to teach future generations?

Relationship & Emotion (41–60)—for partners and close friends

1. What makes you feel truly seen?

2. How do you express love?

3. What’s an emotional need that’s important to you?

4. How do you like to resolve conflict?

5. What’s a relationship deal-breaker for you?

6. When do you feel most secure in a relationship?

7. What’s one small thing a partner can do to brighten your day?

8. What’s a vulnerability you’re working on?

9. How comfortable are you with apologies?

10. How do you show appreciation?

11. What’s your love language?

12. What’s a memory of feeling loved?

13. What boundaries help you feel respected?

14. How do you recharge after emotional stress?

15. What’s your biggest relationship hope?

16. How do you feel about public displays of affection?

17. What are your thoughts on marriage/commitment?

18. How would you like to celebrate anniversaries?

19. What role should extended family play in a partnership?

20. What dating habit do you want to keep or change?

Past & Life Story (61–75)—encourages storytelling

1. What was your favorite childhood memory?

2. Who was your first true role model?

3. What’s a difficult lesson you learned young?

4. What hobby did you love as a kid?

5. What’s a turning point in your life?

6. What’s one thing from your past you’re proud of?

7. What’s a habit you carried into adulthood?

8. What’s a friendship that shaped you?

9. What was your favorite teacher like?

10. What town or place feels like “home” to you?

11. What’s a mistake that taught you something valuable?

12. Who did you go to when you needed advice growing up?

13. What book influenced you most as a teen?

14. What tradition from childhood do you want to keep?

15. What do you wish you’d known at 18?

Future & Dreams (76–88)—motivates shared planning

1. What’s one goal for the next five years?

2. Where would you love to live someday?

3. What career dream would you still pursue?

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

5. What would your ideal retirement look like?

6. What’s a skill you want to learn?

7. What legacy do you hope to build?

8. What’s one big trip you must take?

9. How do you picture your ideal home?

10. What would you do with unexpected free time?

11. What social impact would you like to make?

12. What daily ritual would you keep forever?

13. What’s a fear you want to overcome?

Playful & Curious (89–95)—lighten the mood

1. If you could have one superpower, what would it be?

2. Which fictional world would you live in for a week?

3. Pancakes or waffles?

4. What’s your funniest embarrassing moment?

5. If you could swap lives with anyone for a day, who would it be?

6. What’s the weirdest food combination you secretly like?

7. What’s one silly habit you’ll never give up?

Why these questions work (authority & science)

Turn these prompts into multi-format keepsakes on Tellsomething