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116 Deep Questions

That Will Strengthen
Your Connection
Last Updated: October 27, 2023

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.

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DeepQuestionsPRINTABLES

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?

There’s no limit when it comes to deep questions

to ask your partner. They will often lead to thought-
provoking conversations that can tighten your
bond. Spruce it up by trying to guess each other’s
answers! Pair these conversation starters with a
romantic gift or journal, so you can document any
surprising things you find out about your partner.

You can also use games to understand your

significant other more profoundly. By playing
games such as “Desert Island” you might discover
something new — learning the three things
someone can’t live without is a window into their
core personality.

No matter your relationship status, asking deep

questions will help you strengthen your romance
and companionship.

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