While working on a recent advice column about screening dates, I highlighted the power of open-ended, thoughtful questions as a way to move beyond surface-level chitchat and build more meaningful connections. In that spirit, here are 50 questions to turn to when conversations feel a bit stuck or you’re looking for something with more depth. Some may lend themselves to lighter, casual exchanges, while others invite deeper conversations—so feel free to adjust as needed to fit the flow.

1. What do you think people misunderstand about you the most?

This can reveal their self-awareness and any aspects of their personality that might not be immediately obvious.

2. What are three things you’re most grateful for right now?

This taps into their values and shows how they view the positives in their life.

3. What’s something that always brings a smile to your face, no matter what?

A light-hearted question that reveals their sources of joy and positivity.

4. If you could live anywhere in the world for a year, where would you go, and why?

This can show whether they’re adventurous or if they have a strong pull toward certain places or cultures.

5. What’s a piece of advice or motto you live by?

A way to find out their guiding principles or philosophies.

6. How do you measure success, and what does it look like to you?

This can reveal a lot about their motivations, values, and what they’re striving toward.

7. If you could change one thing about the world, what would it be?

This shows what issues or causes they’re passionate about and how they think about global problems.

8. What’s the best adventure you’ve ever been on, and what made it so special?

This opens the door to hearing about their travels, favorite experiences, and sense of adventure.

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

An insightful question if this is something that’s important to you, as it can reveal compatibility in values and beliefs.

10. How would your closest friends describe you?

This can provide insight into how they view their own personality and friendships. Also, it’s fun to ask your friends this question—the answers may surprise you! And if not, it’s a nice little ego boost.

11. What does an ideal work-life balance look like to you?

A question that can help you understand their priorities and how they allocate time to different aspects of life.

12. What’s a risk, either personal or professional, you took that paid off—and one that didn’t?

Revealing their relationship with risk-taking, ambition, and resilience.

13. What are the holidays like for you? What are your traditions? Do you like/care about celebrations like birthdays or does it not matter so much?

This question can reveal their preferences, role models, and what they value.

14. How would you define happiness for yourself?

A glimpse into their perspective on what brings fulfillment and joy to their life.

15. What’s one dream you’ve had since childhood that still feels important to you?

A chance to hear about their long-term aspirations and any dreams they’ve carried with them over time.

16. What’s something you’re passionate about that most people wouldn’t guess?

This invites them to share something unique about themselves and often leads to interesting conversations about unexpected hobbies or interests.

17. If you could design your ideal day, what would it look like from start to finish?

You’ll get insight into what they value in a day—whether it’s adventure, relaxation, productivity, or quality time with others.

18. What’s something you hope to accomplish in the next year? Five years?

This lets you see their aspirations and whether they align with your own future plans.

19. What role do family and friends play in your life?

You’ll learn about the importance of relationships in their life, as well as any dynamics that could be essential to know in a romantic context.

20. What kind of relationship do you have with yourself?

A deep, introspective question that can reveal their self-awareness and attitude toward personal growth.

21. Is there a book, film, or experience that’s significantly shaped who you are today?

This question allows them to reflect on influential life moments, giving you a window into their beliefs and formative experiences.

22. When you’re feeling overwhelmed or stressed, what do you do to decompress?

Knowing how they cope with stress can help you see if your lifestyles and emotional needs match.

23. What’s something you used to believe but don’t anymore?

This can show you how open they are to change and self-reflection, and whether they’re willing to evolve over time.

24. What’s your idea of a healthy, balanced relationship?

You’ll gain insights into their relationship values and see if they match up with your vision for a partnership.

25. How do you approach difficult conversations?

This reveals their communication style and whether they can handle conflict in a healthy, productive way.

26. What’s the best compliment you’ve ever received?

This question can hint at what they value most about themselves and what they’re proud of.

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

This brings out their wisdom and self-reflection, showing what they’ve learned from life so far.

28. What’s something you’d love to learn or try, and why haven’t you yet?

A great way to find out about their aspirations, and whether they’re open to new experiences and growth.

29. How do you like to spend time with people you’re close to?

This shows their love language and how they value quality time, as well as compatibility with your own social preferences.

30. When you’re going through a tough time, what’s the best way someone can support you?

This can reveal how they like to receive care and comfort during difficult moments.

31. How do you approach disagreements or conflict in relationships?

A critical question for understanding their conflict resolution style.

32. What’s something you’re currently working on improving about yourself?

A gentle way to explore their openness to self-growth and personal development.

33. What’s the most important lesson a past relationship has taught you?

A way to see how they view past experiences and if they reflect on them constructively.

34. When you imagine a long-term partnership, what does that look like to you?

Gives insight into their vision for the future and their expectations of a serious relationship.

35. What are three qualities you think are essential in a relationship?

A great question to check for alignment on values and priorities.

36. How do you usually handle stress, and what helps you relax?

This question can reveal their coping mechanisms and if they practice self-care.

37. Is there a life philosophy or value you try to live by?

Shows what drives them and what’s meaningful in their daily life.

38. What kind of legacy would you like to leave behind?

A deep question that reveals their long-term aspirations and the impact they hope to make.

39. When it comes to money, do you have a particular philosophy or approach? Are you a spender or saver?

Money often plays a big role in relationships, so this helps reveal how they manage or think about finances.

40. What are some of your pet peeves?

A light-hearted way to get a glimpse of their tastes and annoyances.

41. How do you feel about trying new things or breaking out of routines?

Helps you understand their attitude toward novelty, change, and adventure.

42. What’s something that’s making you happy these days, and why?

This question can spark a meaningful discussion on what truly excites and drives them.

43. How often do you want sex ideally? What kind of sex are we talking about?

Not a first date question perhaps, but important to know for long-term compatibility and expectations.

44. What’s a cause or issue you really care about?

Offers insight into their values, passions, and if they’re involved in activism or charity work.

45. How important is humor to you in a relationship, and what makes you laugh?

Laughter is often a core element of compatibility, and this question digs into their sense of humor. Or at least gets them to share some animal memes you might not have seen.

46. If you could wake up tomorrow with any new skill or talent, what would it be?

A fun way to explore their interests and any dreams they may not have pursued yet.

47. How do you envision it in a future partnership? Marriage? Kids? Pets?

An opportunity to discuss family dynamics and expectations, which are often key in relationships.

48. How social are you? How often do you invite people over or go out? What’s an ideal Friday night for you?

This question helps reveal your partner’s social preferences, whether they’re introverted, extroverted, or somewhere in between. Understanding how they like to spend their downtime and weekends can clarify if your social styles align—an important factor in balancing shared and solo time together.

49. Do you cook? How do you split chores with a partner? What are your views on splitting expenses, especially if one of you makes significantly more money?

Knowing their approach to cooking, chores, and expenses provides insight into how they share responsibilities in a partnership. This question can help you gauge if they value balance and fairness in practical areas, which are crucial for a harmonious, long-term relationship.

50. What’s one thing you think every successful long-term relationship should have?

A chance to discuss core values around what makes a relationship thrive.