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127 Deep Questions To Ask A Guy – Ways to Spark A Lasting Connection!

If you’re searching around for some deep questions to ask a guy, I have you covered!

Whether you’re a few dates in or you’re just starting to get serious, here are some funny, serious, hard-hitting and dreamy questions to ask a guy to get to know him better on a lot of different fronts.

And if you’re wondering how to start a conversation with a guy at all, these questions are here to be your wing-woman! These are awesome, effortless segues leading to some good laughs and, hopefully, deeper friendship and intimacy. Let’s start!


17 Best Deep Questions To Ask a Guy

These are the very best of the deep questions to ask a guy. You can’t go wrong with these thought-provoking and interesting queries. 

And don’t shift gears after they reply – use their answer to learn even more about their background and their interests!

Here are the 17 best deep questions to ask a guy:

1. Are you more afraid of failure or success?

Both are a risk – which way does he lean?

2. Do you believe in giving people second chances, and why?

This gives insight into how trusting he is, and how resilient he is.

3. What life-changing event have you experienced?

Did it affect him in a positive or negative way?

4. How do you feel about infidelity?

Can a relationship survive this level of betrayal?

5. What do you think is humankind’s greatest invention?

Sliced bread? Indoor plumbing? The internet? There are countless answers!

6. What are you passionate about in life?

And is he doing something to make it a priority?

7. What important lesson have you learned from a family member?

Ten bucks bets he learned it from his Grandma.

8. What quality in a person do you fall in love with?

Whether its a sense of humor or bravery, there is something that he values most.

9. Do you find it difficult to admit that you are wrong, and why?

How much of a growth mindset does he live in?

10. Who or what inspires you?

Maybe an artist, a revolutionary, or a place?

11. What do you think prevents people from realizing their dreams?

What does he think gives people the push to step out and go after them?

12. What makes you nostalgic?

It could be certain foods or smells, or maybe it’s a holiday tradition.

13. Have you made someone cry?

Was it on purpose or an accident? Did he make it right?

14. How would you spend your remaining time if you found out you only had 10 days left to live?

What unfinished business needs to be wrapped up?

15. Are you a dreamer or a go-getter?

The difference is how action-based a person is.

16. Are humans fueled by greed or by love?

Which one is the larger motivator? Which one produces the most results?

17. Have you ever had a brush with death?

Did his life flash before his eyes?

16 Deep Questions To Ask a Guy To Get To Know Him

If you want some questions to ask a guy to get to know him, this sub-list will help you learn more about the way he experiences the world.

Here are 16 questions to ask a guy to get to know him:

18. How do you feel when things are not going your way?

If his answer is anything like, “throw a tantrum,” it’s a hard pass.

19. If you woke up tomorrow with no fear, what would you do first?

What’s at the top of his bucket list?

20. What will people say about you at your funeral?

What are the nicest things? What are the worst possible things?

21. Do you believe we make our own happy endings, or is fate responsible for them?

What does free will mean anyway?

22. Are you afraid of dying?

It’s going to inevitably happen – what can be done to deal with that fear?

23. When have you felt your biggest adrenaline rush?

Find out if he is an adrenaline junkie.

24. If you could change one thing about the world, what would it be?

No more hunger, peace abounding, the ability to teleport… there are endless answers!

25. If you could pick a new “golden rule,” what would it be?

Just a reminder, the first one is if you don’t have anything nice to say, don’t say anything at all.

26. Is failing less, equal or more important than succeeding?

An innovator will have a different opinion than an advisor.

27. Do you think you can have multiple best friends or only one?

How does he know someone is his best friend?

28. How should household chores be divided?

Free for all, first come – first pick, designated jobs? What does his ideal system look like?

29. Where would you go if you could teleport anywhere in the world?

The beach or the mountains? Maybe a different time?

30. Why is it sometimes hard to forgive others?

Is it punishment, or fear?

31. Do you make decisions more with your head or heart?

Does he wish he had a different process?

32. What message would you put on a billboard that thousands of people would see every day?

Mine would be, “you can do hard things.”

33. Has anything ever happened to you that you could not, and cannot, explain?

The supernatural or the ultra-complicated, anything goes.

16 Deep Questions To Ask a Guy You Like

This is a great collection of questions to ask a guy you like to learn even more about him and show him that you’re really interested!

And don’t be afraid to send some clear visual clues you’re into him, too. Make the most of this one on one time!

Here are 16 deep questions to ask a guy you like:

34. When do you think a person is ready for marriage?

Is there a checklist, or just a feeling?

35. What do you do when no one else is around?

Not just the definition of character, but, really, what does he do? Dance around with his cat? Drink milk from the carton? Read classic novels?

36. What are your thoughts on online dating or tinder?

Does he know any couples who have met through an app?

37. What do you think is the foundation upon which every relationship is built?

Which core value is the most important?

38. How will / did you know you are in love?

Many people have a specific trigger, like wanting them to meet your family or never screening their calls.

39. What makes you happy?

Not joyful, not content or ecstatic, just happy.

40. If you could take a year-long paid sabbatical, what would you do?

Maybe an around the world adventure, or maybe visiting with all of his favorite people.

41. Do you think trust can ever be rebuilt once it has been broken?

What are the steps for that, and who gets to decide?

42. What’s your earliest memory?

Is it a real memory, or just a story he’s heard retold over and over.

43. How do you express gratitude towards others?

Is a simple “thank you” enough, or does he like to be more elaborate?

44. How do you like to be comforted when you’re upset?

Some people are touchers, and some are not. It’s best to know which in advance!

45. When was the moment in your life you laughed the hardest?

He probably will laugh retelling it.

46. Would you live 120 years that are cozy but boring or live half as long, but have an interesting adventure-packed life?

Ask him what a successful life means.

47. Can you sacrifice yourself for a stranger?

Does it depend on who the stranger is?

48. If given the choice, what would be your last words?

“I was right” are some good ones.

49. Do you think relationships are intended to last eternally?

What about the idea of soul mates?

17 Deep But Fun Questions To Ask a Guy

Looking for some fun questions to ask a guy? This list is a great one to break out when you’re on a fun, adventurous date, or when you want to amp up the silliness!

Laughter grows trust which grows intimacy – build on that!

Here are 17 deep but fun questions to ask a guy:

50. As a force, are we humans creative or destructive?

Or does it depend on our season of life?

51. What is something that never ends well?

It probably is something like a sentence that starts with, “you always…”

52. What movie scene would frighten you the most if it happened in real life?

Something from a slasher movie? Or maybe a scene from the Hangover?

53. Which one fits you better? “Live for the moment”, or “Save the best for last”?

What does that mean in relationships?

54. When things break, do you prefer to fix them or replace them?

Also, can he fix things?

55. In what areas do you want to change the most?

This is a good way to see how self -aware he is.

56. When you were a kid, what did you think being this age would be like?

Flying cars and healthy cake for every meal??

57. Is surveillance ever a bad thing if you have nothing to hide?

What does privacy truly mean, and is it important?

58. Have you ever questioned your sanity?

What brought him to that place?

59. What’s one thing about you that you’d never mention on a first date?

Hint – ask this on a first date just to get the ball rolling!

60. Where do thoughts come from?

Are we in the matrix?

61. How can people believe in truths without evidence?

Is faith a part of his life?

62. Have you ever changed your plans because of your horoscope?

How much power does he feel he holds over his future?

63. Is a person ever truly evil?

What if they were made that way through trauma?

64. If you knew that sacrificing your life would have a huge benefit to thousands of people, would you do it?

What would you do first?

65. What is an acceptable measure of one’s life?

What needs to be checked off the list for success?

61. Have you wasted your potential or lived up to it?

Does he feel that he or someone else has the highest expectation of himself?

15 Deep But Funny Questions To Ask a Guy

Deep questions don’t have to be serious all the way. These funny questions to ask a guy eke out some of his inner workings while still keeping things light!

Use this list in your uber, or while waiting for your table at a restaurant!

Here are 15 deep but funny questions to ask a guy:

62. If you catch a fish, do you eat it or let it go?

Is it different than eating a fish from the store?

63. Do you think you can overdo practice?

It takes 10,000 hours to become an expert. But, what if a passion takes over your life?

64. If we evolved from monkeys, why are there still monkeys? And does that mean we are, deep inside, monkeys?

And what makes us different from other, wild monkeys??

65. Does observation alter an event?

What about fear, or time?

66. What is real beauty?

And who gets to decide?

67. Do you think mascots smile beneath their costumes?

My guess is it’s too hot to smile…

68. Have you ever counted your steps while you walk?

Do you think electronic step counters are accurate?

69. Do you use something labeled as disposable for more than once?

What are some creative ways to reuse?

70. If you had to bury treasure where would you hide it?

And would you leave a map?

71. What’s one thing that’s happened in your life that has made you feel like a stupid person?

Most of us have a moment like this burned into our minds.

72. Are jokes half-meant?

And should we call them jokes?

73. Do you think they should discontinue printing newspapers?

Is it a dying industry?

74. If your life was a movie, how would the beginning of it look like?

Mine would start with a montage.

75. Do you think it is possible to remember to forget?

Can you train your mind to let go?

76. What is something others find funny that you find offensive?

Bathroom jokes, gallows humor, or something else?

17 Deep Interesting Questions To Ask a Guy

Get into some philosophy! These interesting questions to ask a guy will get his gears spinning and will help you discern just how in sync your views on things are!

But never fear if you have ultra-different perspectives – you may have a lot to teach each other!

Here are 17 deep interesting questions to ask a guy:

77. Do you think this world will ever end?

How can we prepare??

78. Is technology an ally or an enemy?

What is AI and how does it impact humanity?

79. Is your job now a reflection of what you said you wanted to be when you were a kid?

I mean, basically, everyone wanted to be a veterinarian!

80. What do you think of best friends of the opposite sex?

Are they a threat to relationships, or do they offer a shift in perspective?

81. What is something you’re judgmental about?

It’s ok to sometimes have a judgy face.

82. Do you believe in heaven?

If not, what do you think lies after this life?

83. Are you a person who keeps enemies, grudges or any negative thoughts about a person?

Find out now how carefully you need to tread.

84. Have you ever felt tempted to commit a crime?

And, has he committed any crimes?

85. In what area of life do things never seem to go your way?

Is it just a weak spot or a character flaw?

86. Are you confrontational?

And if so, how does he start those conversations? How do people react?

87. Do you think you are better today than you were yesterday?

If so, what made the shift??

88. Are you open to changes?

How big of changes? The city he lives in? His career? Becoming a vegetarian??

89.Are you comfortable with being uncomfortable?

Does he learn best in the discomfort, or when he has the freedom to learn without risk?

90. Have you ever been in trouble with the law?

What was the outcome? Was it worth whatever risk he took?

91. Do you ever feel the need to have total privacy?

What is he afraid people might see?

92. Do you think all diseases will be cured someday?

Or are there some things that will always threaten us?

93. What is one bad habit we are all better off without?

Maybe cracking knuckles or loud conversations in public spaces.

19 Deep Random Questions To Ask a Guy

Use these random questions to ask a guy to play your own personal version of speed dating. Set a timer and go through this list, alternating answers.

Here are 19 deep random questions to ask a guy:

94. What are your religious views on marriage?

Should people be the same religion or can families have mixed backgrounds?

95. Do you long to be with the person all of the time?

What is his ideal balance of alone time to connection time?

96. What is your biggest fear about marriage?

Failure? Losing himself? Something else?

97. Do your feelings have an unusual and powerful intensity?

What are some big triggers?

98. What’s more important, work or family?

And work isn’t just a job! A passion project counts, too.

99. Given the ripple effect of our actions across time and space, how can we ever be sure that we’re doing the ‘right’ thing?

Right can mean so many things, how can we know we are going the right direction?

100. Do you believe love can pull you through anything?

Love can be an anchor, for good or for bad.

101. Is everything we know subject to debate?

Have him give you three reasons why!

102. How well do you budget?

This is a practical one – a spendaholic can be a dangerous partner.

103. What do you need to feel fulfilled in life?

Is it zeros in a bank account, a job title, acclaim? Something else?

104. Do you feel it is important to save for retirement?

If not, what’s the long term plan?

105. What does being honest with yourself means?

Ask about his methods for checking against his own wisdom.

106. Does anyone in your family suffer from alcoholism?

How does his family support them?

107. When do you feel that you are at your best?

What does he look like whole-hearted?

108. Is suffering an important part of being human?

Can we live a meaningful life without it?

109. How do you think life will change if we got married?

For good or for bad – get a realistic answer

110. How important are anniversaries to you?

Make sure to think through other people’s anniversaries and his own.

111. Should prisoners with full life sentences be given the chance to end their life rather than live out their days locked up?

Who decides the value of a life?

112. Do you think you have ever pretended to be good at something when you really aren’t?

How long ’til he was found out?

15 Deep Personal Questions To Ask a Guy

Make sure you use these personal questions to ask a guy with care! Like all of these questions, you may tread on tender ground. Have fun, but hold space for him to be vulnerable. 

Here are 15 deep personal questions to ask a guy:

113. Where is the line between insanity and creativity?

Or is it intermixed?

114. Do you think people are more influenced by their environment or by their biological traits?

Nature versus nurture is an argument for the ages.

115. What is one thing no one realizes about you?

Hidden talent? Hidden fear?

116. Who defines good and evil?

And is it different depending on who is telling the story?

117. What do you think keeps people in toxic relationships?

Fear? Love? A desire to better the world, starting with this person?

118. Do you believe in things you do not physically see?

Ghosts, gravity or otherwise?

119. How do you know your perceptions are real?

Let’s go over the storyline of Inception once more.

120. Do you ever wish you’d handled a situation differently?

How long was it before you were able to put it aside as the past?

121. If your significant other lost his/her job and decided to just not work anymore, what would you do?

Does the salary load need to be equally distributed?

122. What are your thoughts on homeschooling?

Is it weird long skirts and big vans or prodigy style kids graduating early?

123. Is it worse to fail at something or never attempt it in the first place?

The goals version of “is it better to have loved and lost.”

124. How would you feel if our kids wanted to join the military rather than go to college?

What about trade school? Is there a more socially acceptable path?

125. Where does the soul live?

The heart, the mind, or outside the body?

126. How involved do you want grandparents to be in your parenting?

Does he feel like the earlier generation is outdated or that they have timeless wisdom to share?

127. What values do you want to install in your children?

Let’s say, top 4?

3 Deep Questions To Ask Your Boyfriend

When you’re ready to take your relationship to another level, try using these deep questions to ask your boyfriend to make a stronger connection.

Here are 3 deep questions to ask your boyfriend:

128. Do you believe more in fate or that we are the creators of our own destinies because we are governed by free will?

Big questions like this are always a great way to spark deep conversations.

129. What would you consider your greatest accomplishment so far?

This is nice to ask to see how he defines accomplishment.

130. What is the greatest struggle you’ve overcome?

Our struggles don’t define us, so much as shape us to build deeper character. A great question for anyone, not just people who have lived a hard life.

How To Pick The Best Deep Questions To Ask A Guy

Wondering how to sort through this in-depth list of questions? I’ve made a quick guide to help you choose questions that will add depth and affection to your relationship, not add stress.

Here is how to pick the best deep questions to ask a guy:

1. Read the room

Gauge how you and your guy are doing emotionally. Are you having fun? Are you feeling connected? Is there underlying stress?

Get a good read on how much bandwidth you have when it comes to choosing questions and having deep conversations.

2. Pick questions that lead to connection, not conflict

Read through this list, and choose questions that fit where you are. Feeling playful? Go for some light-hearted questions. In a thoughtful mood? Try asking some of the more meaningful questions.

These questions can also be great when it comes to easing some tension – choose some of the funnier questions, and let the silliness relieve the stress.

3: Don’t stop after the answer

While many of these questions could be answered quickly, let them be a diving board into some deeper conversation!

Remember, this isn’t a checklist! Maybe just one of these questions leads to days of conversations for you and your guy. Let the conversation take its winding course, pressure-free.

Downloadable and Printable List of Deep Questions To Ask A Guy

Here is a downloadable and printable List of Deep Questions To Ask A Guy (right click the image and select Save Image As…):

More Great Ways To Talk to Guys

  1. If you’ve been looking for some foolproof info on how to ask a guy out, here is the go-to guide to get the date!
  2. Not sure how to flirt with a guy without being super awkward? Check out this list to take you from bumbling to expert level!
  3. This day and age, it can be hard to know when it’s your turn to make a move. Let us help you know what to do when you’re thinking, should I text him?

In Conclusion

I’m sure these deep questions to ask a guy will lead to many fun, familiar conversations! Family, work, fears, hopes, and existential dread – this list covers all the bases, and there hundreds of curious questions to ask a guy to start building a deeper connection

As you plan out how to start a conversation with a guy you’re interested in, try busting out some of these fun discussion topics! These are a bold and surprising way to get the ball rolling or to take a relationship to new levels. Have fun!

About The Author


Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on, iHeart Media, Elite Daily, and The Urban List. Jasper lives in Georgia with his new bride.

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