Skip to content

Deep Questions to Ask

  • 906 questions
  • 7 days free
  • No account needed
  • iPhone

A deep question is simply one that can’t be answered on autopilot. “How was your day” has a stock reply loaded and ready. “What part of your life feels like a puzzle you can’t solve” doesn’t, which is why the pause before the answer is usually longer than the answer itself.

Depth is the only thing these questions have in common — the subjects vary widely. Some look inward at a single life: the irrational fear you carried as a child, what you’d change if you knew where to start, what your past taught you to avoid. Others look at what has happened between two people: when you last felt genuinely vulnerable, what surprised you, what you regret saying.

They aren’t couple-specific. Plenty of them work with an old friend on a long drive, or as something to sit with alone. If you specifically want questions about your relationship, DeepJoin has collections built for that; this one is about depth itself.

One practical note: ask fewer than you plan to. Three questions with real answers beat fifteen skimmed, and the second question in a row rarely gets the attention the first one earned.

This week’s picks

Three of the collection’s highest-rated questions, by votes and saves from people using the app. The three shown change every Monday.

  • 01

    What trauma would you need to tell me about so l can better understand you?

  • 02

    Are there topics in our relationship that you consider “off-limits”?

  • 03

    What is the most touching and happiest moment in your relationship?

Get DeepJoin

Free for 7 days. No account needed to start.

The full list

Ranked by how people using the app voted on them.

  1. What is my biggest fear?

  2. What do you consider your greatest victory and your greatest mistake?

  3. How do you think we can help each other grow personally?

  4. What are your core life values, and do you feel like you live according to them?

  5. Do you have habits you want to change, and why?

  6. What is your main rule in a relationship that you never break?

  7. What role does love play in your life?

  8. What is your attitude toward finances in a relationship?

  9. What destroys love in most cases? Name the top 3 reasons relationships end, in your opinion.

  10. Are you a jealous person? Do you think jealousy is a sign of mistrust?

  11. If you had the chance to change something in your life, what would you change?

  12. Recall the most beautiful moment in your relationship over the past year.

  13. What is your biggest fear in a relationship?

  14. How can we strengthen the trust between us?

  15. Name 3 things you’d like to change about your partner’s character.

  16. Can someone be in a relationship and still feel lonely?

  17. How do you feel about compromises in a relationship?

  18. Are there topics in our relationship that you want to discuss but don’t know how to bring up? How can I help?

  19. Have you ever felt unnecessary in our relationship? Tell me about it.

  20. What's an insecurity of mine that you love?

  21. What is your definition of an ‘ideal relationship’?

  22. Are you ready to accept your partner’s past without judgment?

  23. When was the first time you realized you wanted to be in a relationship with me?

  24. Is codependency in a relationship good or bad?

  25. How do you feel about showcasing your relationship/family/children on social media?

  26. Is there something from your past that you haven’t shared but consider important?

  27. How can we improve our emotional intimacy?

  28. What's something about yourself you've discovered or improved upon through our relationship?

  29. How can I support you when you're feeling stressed or upset?

  30. Do you believe that it is important to openly talk about your fears and worries?

  31. How do you feel about discussing emotions in a relationship?

  32. What do you think makes our relationship unique?

  33. What do you think each of us contributes to the relationship that makes it better?

  34. Is there a part of you that you fear I might never fully understand or accept?

  35. What is the greatest sign of trust in a couple for you?

  36. What is your opinion about long-distance relationships?

  37. Imagine I suddenly experience a major career failure and lose all my savings. How would you support me during that time?

  38. What is your biggest fear in our relationship?

  39. How do you recover from personal crises or losses?

  40. How would you like me to express my appreciation for your efforts and support?

  41. Are there moments when your partner crosses your personal boundaries? Give an example.

  42. How can I support you in your aspirations for the upcoming year?

  43. Do you think we could stay friends if our relationship ended?

  44. What attracts you most in our relationship and makes us unique as a couple?

  45. What small things in our relationship make you feel truly loved?

  46. What's the most significant compromise you've made for our relationship, and how do you feel about it?

  47. Are rituals in a relationship, like evening café visits or morning coffee, important to you?

856 more questions in the app

This page shows the best of the collection. The rest — and every other collection — lives in DeepJoin.

Get DeepJoin

Nearby collections

Different mood, same two people.

All collections

Ask a better question tonight

Free for 7 days. No account needed to start.

Download on the App Store