The depth of the bond shared between people in a relationship is best understood if both partners ask thoughtful and significant questions to each other. Deep questions when asked in a romantic relationship can prompt meaningful and deep conversations, heighten emotional intimacy, build strong connections, and help strengthen solid chemistry between the partners. The partners can know more about each other’s significant perspectives and even reflect on their values and feelings. In moments of vulnerability, these deep and tough relationship questions can help individuals explore other people’s goals, emotions, and dreams.  

If you wish to have a true compatibility check in your relationship, you can start your conversation by asking any of our list of the diverse range of 101 deep and tough Intimacy questions.

Catalog of 101 Tough Relationship Questions to Enhance Your Connection

Deep Relationship Questions to Ask your Partner

1. What have you learned from your failed past relationships?

2. What will be your reaction, if I forget your birth date?

3. What changes do you want from me to serve you as a better partner?

4. Am I giving you enough space in our relationship?

5. Are you comfortable sharing your problems with me?

6. What thought comes to your mind first when you wake up?

7. What things can make you angry?

8. Do you think our bond will last for a lifetime?

9. What is a relationship deal breaker for you?

10. Are you feeling safe and protected with me?

11. What kind of partner you would love: seductive, smart, jolly, or nurturing?

12. Do you like spending time alone or do you prefer good company?

13. Would you go the extra mile to help someone?

14. Do you think the best is yet to come in our relationship?

15. When do you feel most unguarded?

16. What was the first thing that you noticed in me that got you attracted to me?

17. How would you like to hang around with me?

18. What are the most stunning traits that you would love to see in your life partner?

19. Are you comfortable with my family?

20. Do you wish to see any changes in me or yourself?

21. What is most important to you in a person: intellect or physical appearance?

22. Do you find me caring and sensitive?

Deep and Romantic Relationship Questions to Ask your Beloved

23. Do you believe in the existence of soulmates?

24. Do you believe in getting married?

25. Would you like to dine with me in a quiet place or at a nightclub?

26. What kind of partner do you prefer: dominating or submissive?

27. What will be the best gift you would like to receive from your lover- a precious piece of jewellery, a modern gadget, or a weekend trip?

28. How do you want your marriage to be a simple ceremony with only close relatives and friends or a theme wedding with a lot of guests?

29. What are you thinking about a perfect romantic date?

30. How do you wish to celebrate Valentine’s Day?

31.  When was the last time thoughts about me came to your mind?

32. What is the most attractive thing according to you in a potential life partner?

33. Which is your best-loved fictional couple?

34. What destination do you prefer to spend your holiday: a hill station, museum, beach, or wildlife?

35. Do I like to have surprises or want everything to be planned?

36. Would you like to sign up for a couple of dance classes?

Deep Intimacy Questions to Ask your Lady-Love

37. What are your thoughts on the #MeToo movement?

38. What peculiar smell do you enjoy?

39. What are your thoughts on being a woman?

40. What is the recent thing that you learned that you must have known before?

41. Would you like to go ahead with what is considered masculine from age-old times?

42. How do you feel about the way females are depicted in any movie, series, or TV show?

43. What’s your viewpoint on why every female should become a mother?

44. What is the most satisfactory thing that you have done in your past?

45. What’s your thought on female orgasm being a myth?

46. Have you ever been “mansplained”? What was your reaction to it?

47. Would you like to regularly keep a check on your partner’s phone?

48. What do you think people assume about you just after seeing you?

49. What will you do if your partner is not liked by your parents?

Deep Relationship Questions to Ask your Boyfriend

50. Are you happy with your job?

51. What do you think about a woman?

52. What according to you is a masculine man?

53. Have you ever been pressured in your family or relationship?

54. What challenges do you come across as a man in today’s time?

55. Should a man express his emotions?

56. When do you think is the right time to get married?

57. What does society feel about a man?

58. Would you stop loving your spouse if she is diagnosed with a non-curable illness?

59. Is your current work in line with what you wanted to become when you grew up?

60. How do you feel responsible for pushing your relationship a step forward?

61. Do you like to go on online dating or swipe on dating apps?

62. How do you make friends with other guys?

Deep and Serious Intimacy Questions

63. Are you conscious about anything?

64. How do you deal with stressful situations?

65. What are the pros of being in a healthy relationship?

66. What parenting style will you have for your children?

67. What scares you the most about commitment?

68. Do you believe in monogamy?

69. Do you like to have kids?

70. What will you do if your partner is having a physical disability?

71. Can you overlook everything from your parent’s past?

72. Is there anything that gives you formidable anxiety?

73. After a dreadful day would you like to end your day with a tasty dinner or go on a cosy movie night?

74. What things are you reluctant to change in your relationship?

75. What do you love the most about yourself?

Deep Relationship Questions to Ask the Love of your Life

76. What made you love me?

77. How often do we fight?

78. Do you think we are made for each other?

79. What is the dearest memory of our togetherness?

80. Which is your favourite family holiday, so far?

81. Do you think we are complete together?

82. Is there any fantasy that you want me to fulfil for you?

83. Do you think I have changed myself over the years of our relationship?

84. What is that thing that you want from my side?

85. Have you ever been jealous of me talking or spending time with friends of the opposite sex?

86. If you want to make a movie on our relationship story- which genre, would you choose?

87. What kind of home do you prefer to live in with me?

88. What things do you remember from our first meeting?

Deep Questions to Ask to Better Know Someone

89. Which city do you dream of residing in?

90. Which book did you love to read in childhood?

91. Are you well-connected with your parents?

92. Who are your best friends?

93. Are you comfortable spending time with my friends?

94. How do you entertain yourself when you are in a low mood?

95. What is the weirdest thing that you have done so far?

96. Name three things that you cannot live without.

97. Are you an overthinker or live with a carefree attitude?

98. When we are financially in good condition, would you prefer trips or buying possessions?

99. What are the most important qualities you look out for in anyone you thinking of building a relationship with?

100. Are you a night owl or a morning person?

101. What are your biggest fears?

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