Starting a new relationship is exciting, full of possibilities, and sometimes a little nerve-wracking. You’re getting to know each other, discovering shared interests, and figuring out if your values align. But let’s be honest—sometimes, small talk just won’t cut it.

If you want to skip the surface-level conversations and really understand your partner, asking thoughtful, unique, and fun questions can help. This list of 100 questions for couples at the start of their relationship will spark deep conversations, playful debates, and even a few surprising discoveries.

Personal Values and Life Perspectives

1. What’s one belief you hold that has shaped the way you live?
2. How do you define success, and do you think you’re on the right path toward it?
3. What’s something about your upbringing that has had a lasting impact on who you are today?
4. Do you believe people can truly change, or do we just become more of who we already are?
5. If you could go back in time and give your younger self one piece of advice, what would it be?
6. What do you value more—stability or adventure?
7. How do you handle stress when life gets overwhelming?
8. What’s one thing you’re actively working on improving about yourself?
9. How do you define personal growth?
10. What does happiness look like for you in everyday life?

Love, Dating, and Relationship Expectations

11. What does a healthy relationship look like to you?
12. How do you express love—through words, actions, gifts, time, or physical touch?
13. What’s your love language, and how do you like to receive affection?
14. How do you handle conflict in a relationship?
15. What’s something small that instantly makes you feel cared for?
16. What’s a non-negotiable for you in a relationship?
17. How do you feel about traditional gender roles in a relationship?
18. How important is physical intimacy to you in a relationship?
19. What’s the best relationship advice you’ve ever received?
20. How do you usually apologize when you’re wrong?

Dreams, Ambitions, and Future Goals

21. If money wasn’t an issue, what would your dream life look like?
22. What’s one goal you’re currently working toward?
23. Do you see yourself living in the same place forever, or do you want to explore different cities/countries?
24. How do you feel about marriage—something you want or something you’re unsure about?
25. Do you want children? If so, how many?
26. What kind of lifestyle do you hope to have in ten years?
27. Would you rather build a career you love or work a job that pays well but isn’t fulfilling?
28. How do you define financial success?
29. What’s your biggest dream that you’ve never told anyone?
30. Do you believe in having a five-year plan, or do you prefer to go with the flow?

Fun and Playful Questions

31. If we could teleport anywhere for a weekend getaway, where would you want to go?
32. What’s your idea of a perfect date night?
33. What’s one quirky habit you have that most people don’t know about?
34. If we had to pick a couple’s Halloween costume, what would it be?
35. What’s a childhood toy or game that still makes you nostalgic?
36. What’s your guilty pleasure TV show or movie?
37. If we could live in any fictional world for a day, where would you choose?
38. What’s one skill you wish you could instantly master?
39. If we created a secret handshake, what move would absolutely have to be included?
40. What’s the most spontaneous thing you’ve ever done?

Family and Background

41. How would you describe your relationship with your family?
42. What’s your favorite childhood memory?
43. Did your family have any unique traditions growing up?
44. How do you handle disagreements with family members?
45. Do you think your upbringing influences how you approach relationships?
46. What’s one lesson you learned from your parents that you want to carry into your own relationships?
47. Do you believe in keeping strong family ties, even with distant relatives?
48. How do you feel about spending holidays with extended family?
49. What’s a funny or embarrassing story from your childhood that you love to tell?
50. What’s a personality trait you inherited from your family?

Dealing with Differences

51. How do you handle situations when you and your partner disagree on something important?
52. What’s one opinion you have that most people find surprising?
53. Are you someone who prefers deep discussions or lighthearted conversations?
54. How do you react when you meet someone with completely different views from your own?
55. What’s something you’ve changed your mind about in the past few years?
56. Do you think people can be fundamentally compatible despite having different personalities?
57. How important is having shared hobbies in a relationship?
58. What’s your view on social media and relationships?
59. How do you deal with misunderstandings in a relationship?
60. What’s a situation where you had to compromise, and how did it turn out?

Money and Lifestyle Choices

61. Are you more of a saver or a spender?
62. How do you feel about splitting expenses in a relationship?
63. What’s your philosophy on financial planning—detailed budgeting or go with the flow?
64. Would you rather live in a big city, small town, or somewhere remote?
65. How important is work-life balance to you?
66. If you suddenly came into a large sum of money, what’s the first thing you’d do?
67. How do you feel about minimalism versus luxury living?
68. Do you think financial compatibility is important in a relationship?
69. What’s one thing you don’t mind splurging on?
70. How do you approach saving for the future?

Deeper and More Reflective Questions

71. What’s something you admire in others that you’d like to develop in yourself?
72. Have you ever had a defining moment that changed your outlook on life?
73. What’s the most valuable lesson you’ve learned from a past relationship?
74. How do you want to be remembered in life?
75. What’s something that always brings you comfort on a bad day?
76. Do you believe in soulmates or the idea of “the one”?
77. What’s one thing you’re grateful for right now?
78. If you could relive one day of your life, which one would it be?
79. How do you define inner peace?
80. What’s one fear you want to overcome?

Just for Fun and Random Scenarios

81. If we started a band, what would our name be?
82. If we could time travel to any era, where would you want to go?
83. If we had to swap jobs for a week, how do you think it would go?
84. What’s one completely useless fact you know?
85. If you had to live in a TV show for a year, which one would you pick?
86. If you wrote a book about our relationship so far, what would the title be?
87. If we had to compete in a game show, which one would you want to be on?
88. What’s one weird habit you have that I might not have noticed yet?
89. If we had a signature dish we cooked together, what would it be?
90. What’s one song that reminds you of our time together so far?

Starting a relationship is a journey of discovery, and asking unique and meaningful questions helps build a deeper connection. Whether you’re getting to know each other’s values, dreams, or just having fun, these 100 questions will create memorable conversations and stronger bonds.

Which question surprised you the most?