53 Questions to Ask in the First Six Months of Dating

Good dating questions give both people room to share what they want. Pick two or three that fit the moment, answer them yourself if you’re comfortable and leave space for a follow-up. Either person can pass on a topic or return to it later.

Some questions become relevant sooner, especially if you’re deciding about exclusivity, intimacy or whether you feel safe. Follow what you actually need to know.

Early dates and everyday life

Start with the way you each like to spend time and what brought you here.

1. What kind of connection are you looking for right now?
2. What do you enjoy doing when you have a free afternoon?
3. What does a good first date feel like to you?
4. What is one thing you would like to try for fun?
5. What is your favorite way to spend a quiet evening?
6. Are you more energized by company or time alone?
7. How does work fit into the life you want?
8. What usually helps you unwind after a long day?
9. What commitments shape your week?
10. What would you like me to know about your family or children?
11. What kind of communication feels natural when dating?
12. How often would you like to see someone at this stage?
13. What makes you feel comfortable meeting someone new?
14. How do you like to make plans?
15. What has made you laugh recently?
16. What are you looking forward to this month?
17. What would you like to know about me?

Values, expectations and boundaries

Talk about these as they become relevant. Ask what an answer looks like in practice.

18. What values guide your biggest choices?
19. How important are your spiritual or religious beliefs in daily life?
20. How would you describe the role of politics in your life?
21. What role do pets play in the home you want?
22. What would make traveling together enjoyable for you?
23. How much time do you like to spend with your friends?
24. How do you make room for friends when you’re dating someone?
25. What is an everyday habit you need a partner to understand?
26. What routines around alcohol, smoking or other substances matter to you?
27. How do you feel about public affection?
28. What are your boundaries around posting about a relationship online?
29. What do you prefer to keep private as a relationship develops?
30. What does being exclusive mean to you?
31. What would help you talk about sexual boundaries and protection?
32. What makes it easier for you to ask for space?
33. How would you like a partner to respond when you say no?
34. How do you know when you need a break during a disagreement?
35. What is one thing you want to learn or change this year?

Commitment, conflict and future plans

If you’re considering more commitment, use these questions to learn what each of you wants. A difference is worth discussing before you make a joint decision.

36. How are you feeling about the relationship right now?
37. What does a healthy partnership look like in everyday life?
38. How would you like us to raise a concern before it builds up?
39. What kind of apology helps you feel heard?
40. How do you want to share time between families or social groups?
41. What kind of support helps you when life is stressful?
42. What have you learned about your own needs from earlier relationships?
43. What are your priorities about where you live?
44. How would you approach a change in work hours or income?
45. How do you think couples should handle shared expenses?
46. What do you consider a fair way to divide chores?
47. How do you want to talk about intimacy when our preferences differ?
48. Do you want children, or do you see your future differently?
49. What commitments about family care already matter in your life?
50. How would you handle a period of long distance?
51. How much independent time would you like in a long-term relationship?
52. How should we revisit an agreement if it stops working for one of us?
53. What is one thing you would enjoy building together?