116 Deep Questions That Will Strengthen Your Connection

Do you ever feel like life’s constant whirlwind keeps you from truly connecting with your partner? The daily grind of work, eat, sleep, and repeat can easily put a damper on those heart-to-heart conversations. But guess what? We’ve got a solution that’ll add some zest to your relationship! Whether you’re sharing a quick bite or snuggling up before bedtime, those little moments can be transformed into opportunities for deeper connection. So, don’t let them slip away. 

We’ve put together a whopping list of 116 mind-boggling questions that are sure to kickstart some seriously fun and meaningful discussions. And the best part? You can download and print them, then stash them in a jar or bind them together with a fancy ring. We’ve even thrown in some blank pages so you can get creative with your own questions and jot down your partner’s captivating answers in our personalized journal designed to capture your unique journey together! 

But wait, there’s more! Games are in on the action too. Ever played “Desert Island”? It’s not just a game; it’s a window into your partner’s core personality! Discover the three things they can’t live without, and you’re in for an adventure. 

No matter where you are in your relationship journey, these deep questions are your secret weapon to add a dash of excitement, strengthen your romance, and take your companionship to new, thrilling heights. 

Deep Questions About Childhood 

1. What is your best childhood memory?
2. What is your worst childhood memory?
3. What was your biggest fear as a child?
4. What was your favorite year of school?
5. What was your favorite subject/class in school?
6. What did you want to be when you grew up?
7. What was your favorite game to play?
8. What is the single most important thing you learned as a child?
9. What is your most memorable family event?
10. What do you admire most about your parents?
11. What do you look forward to about being a parent?
12. If you don’t want to be a parent, why?
13. Do you want to live near or far from relatives?
14. When your parents get old, how do you plan on taking care of them?

Deep Questions About Love

15. When was the first time you said “I love you” to someone in your life other than family?
16. When and where did you go on your first date ever?
17. Do you remember our first date?
18. Were you nervous during our first kiss?
19. When did you know you loved me?
20. What is your ideal night?
21. What is your favorite thing about me?
22. Do you believe in true love or love at first sight?
23. Do you think people are made for each other?
24. Where is the perfect honeymoon locale?
25. Describe a fun date that only costs $20.
26. Describe the most romantic date you can think of — spare no expense!
27. If you were on a dating game show, what questions would you ask?
28. What is your favorite memory with me?
29. What do you look forward to experiencing with me?
30. Would you rather a night in a fancy penthouse suite or a private beach house?

Deep Questions About Values

31. Would you rather acquire material items or experiences?
32. If it cost the same, would you live in a mansion or a mid-sized house with a lot of land?
33. In what scenario, if any, is it okay to lie?
34. When, if ever, is it okay to break the law?
35. What is the most important lesson to teach a child?
36. How often do you go out of your way to help someone?
37. If you could pick a new “golden rule,” what would it be?
38. What are important societal values? (ex. Democracy, fundamental rights, etc.)
39. How have your values changed from ten years ago?
40. What do you see as your best character trait?
41. If you could change one thing about your character, what would it be?
42. Would you consider yourself a pessimist or an optimist?
43. When were you the most disappointed in yourself?
44. When were you the most proud of yourself?
45. Generally speaking, do you like the way you look?
46. If you could change one thing about the way you look, what would it be?
47. Do you put as much effort and emphasis on inner beauty as outer beauty?

Deep Questions About Goals and Motivations

48. Who in your family do you view as a role model?
49. Are you inspired by any celebrities dead or alive?
50. What thought or object gets you through the day?
51. Do you find praise or criticism to be more motivating?
52. What inspires you to better yourself?
53. What advice would you give to your children to stay determined?
54. What is the best way to motivate each other?
55. What is your greatest success to date?
56. What do you hope to achieve in the short-term?
57. What is your long-term goal?
58. What is your biggest regret?
59. What mistake did you learn the most from?
60. What are you most ashamed of?
61. Is failing less, equal or more important than succeeding?

Deep Questions About Relationships

62. What do you look for in a friendship?
63. What is/was your longest lasting friendship and how did it last so long?
64. Do you think you can have multiple best friends or only one?
65. Do you think your pet can also be your friend?
66. Do you consider your parents as friends?
67. Do you think opposite genders can maintain a friendship without developing a love interest?
68. What is an unforgivable action?
69. What is your advice for long-distance friendships?
70. Do you have different advice for nearby relationships?
71. In your opinion, can long-distance relationships survive?
72. Do you think a couple should split costs?
73. Do you think it’s better to save money or invest?
74. How should household chores be divided?
75. What do you look for in a significant other?
76. What is the most important thing in a relationship? (e.g. trust, respect, etc.)
77. How often should a couple argue or fight to maintain a healthy relationship?

Deep Questions About Life Events

78. What was your best birthday?
79. If you could only celebrate one holiday each year, what would it be?
80. Do you prefer family events or alone time?
81. Provided there is good weather, do you enjoy indoor or outdoor activities?
82. What is your ideal wedding ceremony?
83. Describe your perfect vacation.
84. What is the best concert you’ve ever attended?
85. What events are on your bucket list? (ex. Lollapalooza, Macy’s Thanksgiving Day Parade, etc.)
86. When, where, and how long was the best road trip you’ve ever taken?
87. Would you rather spend a week in New York City or Los Angeles?
88. Have you ever been camping? What was your favorite part?

Deep Questions About Stress

89. Is there anything that gives you overwhelming anxiety?
90. How do you handle high-stress situations?
91. What is the most stress-inducing thing that could happen at work?
92. What helps you decompress?
93. Is there a smell that instantly relaxes you?
94. After a horrible day, would you prefer a nice dinner out or a cozy movie night?
95. Are you terrified of anything fictional? For example, the supernatural or zombies.
96. What is your biggest fear in life?
97. Do you have any phobias?
98. Do you have any irrational fears?
99. What was the worst nightmare of your life?
100. Do you like to pull scary pranks on people?
101. What is the scariest movie you’ve ever seen?

Deep Hypothetical Questions

102. If you could have one superpower, what would it be?
103. Do you think flying or mind reading is a more functional power?
104. If you could have one human talent that you don’t currently have, what would it be?
105. If you had three wishes, what would you wish for? (excluding more wishes)
106. If you had the power to correct one problem in the world, what would you fix?
107. Where would you go if you could teleport anywhere in the world?
108. If you could be an animal for a week, what would you be?
109. If you could be an object for a day, what would you be?
110. What would you do if you won the lottery tomorrow?
111. If you could eat anything you wanted right now, what would you order?
112. You’re going to outer space — what planet do you want to see?
113. If the world ended tomorrow, what would you do on your last day?
114. Would you rather go back in time to see the dinosaurs or jump forward a thousand years to see our futuristic society?
115. If you could make one book or movie a reality, which would you choose?
116. If you could be a character from a hit television show, who would you pick?