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188 Best Deep Questions to Ask – This is the list you need.

188 Best Deep Questions to Ask – This is the list you need.

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When you really want to get to know someone, it’s always a good idea to have a few deep questions to ask up your sleeve. You never know when the conversation might take a more serious turn!

With this in mind, we have gathered this absolutely massive collection of deep questions to ask pretty much anyone. We hope that you’ll enjoy it!

Contents

19 Best Deep Questions to Ask

Are you in a hurry? Then let’s jump right into our top picks.

Here are the 19 best deep questions to ask:

1. Why do people do things that they know hurt themselves and those around them?

This one will definitely get your conversation partner thinking.

2. Are women and men equal?

Depends on how you define “equality,” but in the U.S., women still earn 82 cents for every $1 men make.

3. Which parent are you closer to, and why?

No judging, we promise! We all (secretly) have a favorite parent.

4. Is what you’re doing now what you always wanted to do growing up?

Unless they are a superhero, an astronaut, or a mermaid, they probably aren’t living the dream.

5. Are you more into looks or brains?

Or is it possible to get the best of both worlds?

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

This one should make for some interesting reflections on relationships.

7. Have you ever lost someone close to you?

Tread carefully with this one. If you think you might get someone upset, it’s better to hold it off.

8. Do you believe in second chances?

Better still: have you been granted any, and did you deserve them?

9. What’s one dream you have yet to accomplish?

Never stop dreaming!

10. What are the three things you value most about a person?

Character, intelligence, and a good sense of humor are likely to come up a lot.

11. If you could tell your former self one thing, what would it be?

Our suggestion? That’s the youngest you will ever be.

12. What’s the greatest risk you’ve taken?

That should give you some real insight into the person you are talking to.

13. What makes you want to be alone?

Annoying people? Loud noises? A long day at the office?

14. Where do you find meaning in life?

Brace yourself: some of the answers might tear you up!

15. What helps you decompress?

Chocolate? Good music? Working out?

16. Is there anything you consider unforgivable?

Now that’s deep. There are some things that you just can’t let go.

17. Do you follow your head or your heart when making decisions?

The right approach is probably somewhere in the middle.

18. Who has had the biggest impact on your career choice?

It could be a parent, a teacher, a mentor, a total stranger, or a movie character. Life works in mysterious ways.

19. Do you want a family of your own?

This topic can be sensitive, so think twice before asking.

15 Deep Conversation Starters

Need something to get the conversation going? How about some deep conversation starters?

Here are 15 deep conversation starters:

20. How would you rank these in order of importance: family, career, love life?

A person’s priorities will tell you a lot about where their values lie.

21. Do you have a favorite quote or mantra?

Who knows, you might find it inspiring too!

22. Do you think your zodiac sign accurately describes you?

That’s a great question to ask someone who doesn’t believe in astrology with a passion — it should make for a good laugh.

23. What’s your dream vacation?

You’d be surprised how many people would rather do something else than hit the beach.

24. What actor would play you in a movie about your life?

You can look up that actor’s picture and have fun holding it up to your conversation partner’s face to see if they look anything alike.

25. If you had to lose one of your five senses, which would you give up, and why?

Do you know the movie Perfect Sense with Ewan McGregor and Eva Green? In it, a global pandemic starts to rob people of their senses one by one. That should make for an interesting watch after this question!

26. What’s the best way to end a long day?

A good night’s sleep? A good book and your favorite cocktail? Sign us up.

27. What’s your favorite love song?

That’s bound to be sweet.

28. Do you like romantic movies?

Everyone’s guilty pleasure! Who doesn’t enjoy a good old tearjerker from time to time?

29. What’s your favorite college memory?

A trip down memory lane always makes for a great conversation starter.

30. Do you think you could treat a girl right?

And if so, how?

31. What’s the best book you’ve read?

That one could give you some great ideas for your book club.

32. What’s one meal you could eat every single day and never get bored?

Has to be ice cream.

33. What’s your favorite childhood character?

And made you like them so much?

34. What’s one thing you always procrastinate on?

We are our own worst enemies, aren’t we?

17 Deep Questions to Ask Your Boyfriend

Want to get to know the man in your life a little bit better? We’ve got some great deep questions to ask your boyfriend that should do the trick!

Here are 17 deep questions to ask your boyfriend:

35. What advice would you give to someone who’s just graduating high school?

Get a job is a good one. Also: “Start saving.”

36. Do you want to have children?

It might be best not to ask him that if your relationship is still in its early days.

37. Have you ever lived with a partner?

Hint, hint!

38. If you were told you had a terminal illness, how would you take the news?

You never know what challenges life has in store for you.

39. How important is religion or spirituality to you?

This question can help you discover a side of him you never knew existed.

40. Do you think money can buy happiness?

If he likes to hustle, that’s a great one to ask.

41. Would you sacrifice yourself for a stranger?

We all like to think we would.

42. Do you hold grudges?

That would be good to know — for future reference.

43. When was the first time you said, “I love you”?

More importantly, has he said it to you yet?

44. Do you think relationships can recover from cheating?

Some do, but it takes a lot of work.

45. Is there anything you’re ashamed of?

Don’t we all?

46. How important is it for you to save money?

If you are not saving at least 10% of your income, you are in for trouble.

44. Do you think people can or should be friends with their exes?

Ouch. That’s always a controversial one.

45. What’s your biggest fear for this relationship?

If he says he fears losing you, he’s a keeper.

46. Is love something that scares you?

It should — it’s big, powerful, and life-changing!

47. What’s your favorite way to show affection?

While you’re at it, make sure to also let him know what’s your favorite way of receiving affection.

48. What does love mean to you?

Is love all about big romantic gestures or daily acts of care (read: folding the laundry and taking out the trash)?

12 Deep Personal Questions to Ask

Do you want to really get to know someone’s inner world? Then ask them some of our deep personal questions to ask.

Here are 12 deep personal questions to ask:

49. What did your past relationship teach you?

Everything happens for a reason, and every situation has something to teach us.

50. What’s your biggest regret?

We all make mistakes — there is nothing to be ashamed of here.

51. Would you be with someone who doesn’t have the same beliefs as you?

If they say they wouldn’t, does that make them intolerant?

52. What are you most grateful for?

It’s important to count our blessings: they are far more than we realize.

53. Deep Personal Questions to Ask – Who’s the first person you call when you’re in trouble?

A sibling? A parent? A good friend? Their partner?

54. Did you ever judge someone for the dark secrets they told you?

Let’s face it — we all have.

55. What do you do when you’re angry?

You might learn some useful tips on anger management.

56. What’s the secret to happiness?

Not trying so hard to be happy, perhaps?

57. What would you want to be written on your tombstone?

A joke would be good.

58. Do you get along with your siblings?

You can’t have a family without a little sibling rivalry.

59. How often do you cry?

Crying is good: it’s beneficial for both your physical and your mental health. So, it’s nothing to be ashamed of!

60. When did you last cry in front of another person?

That’s a great follow-up question to the previous one to make the conversation even deeper.

16 Deep but Also Interesting Questions to Ask a Guy

We thought you could always use a few interesting questions to ask any guy, whether he is your partner, a friend, or someone you just met at a party.

Here are 16 deep but also interesting questions to ask a guy:

61. What’s your ideal home?

And where would it be located? On the beach, high up in the mountains, or right in the center of a bustling city?

62. Were you ever called funny names as a kid?

It probably wasn’t that funny at the time!

63. What’s the funniest way that you have been injured?

That should make for some great laughs.

64. What would you say to your President if you ran into them randomly?

How much time do they have? Something tells us you’d have a lot to talk about.

65. Who’s your best friend, and how long have you known them?

There’s nothing quite like a bromance.

66. What would you do if you had a million dollars?

They say that money has a way of revealing one’s real character.

67. Are you a hopeless romantic?

Or a hopeful one?

68. What do you feel is the world’s biggest problem right now?

Where do we even start?

69. What do you feel are your weaknesses?

It’s always great when a guy is not too full of himself and can own up to his weaknesses.

70. What’s one thing that defines who you are?

The answer should tell you everything you need to know about that guy.

71. What’s one thing you want to do before you die?

Everyone should have a bucket list!

72. What’s one thing you could never live without?

If he doesn’t say “Love,” then there’s something seriously wrong with him.

73. Do you think confessions make a relationship stronger?

Depends on the confession.

74. What do you like most about dating?

It better be his date!

75. What do you find attractive in a woman?

That’s always interesting to hear — especially if you are a woman yourself.

76. Where would you get a tattoo, and what would it say?

Or what would it look like?

15 Deep Questions to Ask a Guy

You might want to get your pen out. Our questions to ask a guy will get you answers so deep that you’d just have to write them down!

Here are 15 deep questions to ask a guy:

77. What kind of parent do you think you will be?

Other than a father, that is?

78. What’s the nicest thing someone has done for you?

That will make both of you smile.

80. What’s your stance on women making the first move?

Most guys actually like that!

81. Is poverty an inevitable byproduct of society?

If it is, then we would need to build a different kind of society.

82. What do you consider a wasted life?

A loveless one, perhaps?

83. Why is depression so stigmatized?

Fortunately, that seems to be changing.

84. Will technology be humanity’s salvation or downfall?

So far, it’s been a mix of both.

85. Is free will real or just an illusion?

Even if it is an illusion, it’s probably best to live our lives as if it were real.

86. Is one life enough to complete all our goals and live out our dreams?

Absolutely not! There are way too many cool places to be and things to do.

87. Do you think certain people deserve pain and punishment?

It would be interesting to see what his thoughts on criminal justice are!

88. Can people truly change?

Yes, but only if they truly want it.

89. Do you think we will be rewarded for our charity?

If he says that we should be doing charity regardless of what’s in it for us, then he is a great guy.

90. Are you afraid of death?

Who in their right mind isn’t?

91. Do you prefer the countryside or the city?

Who knows, if you both like the same thing, you might be on to something.

92. Do you think that time does heal all wounds?

That should make for some interesting confessions.

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

Just met a guy who seems very interesting? We’ve got you covered with our awesome questions to ask a guy to get to know him.

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

93. What’s one question you would like to ask any religious deity?

“What’s the point of evil?” would be a good contender.

94. Have you ever gotten into trouble by expressing your desires?

And what were those desires?

95. Were you the same person as a child?

Believe it or not, we actually don’t change that much as we grow up.

96. Do you have a dream?

And what is it?

97. What countries do you dream of visiting?

He might let you in on some cool travel ideas!

98. What’s your most memorable birthday present?

And who was it from?

99. Can you imagine your life without music?

If his eyes light up, you’d already know that the answer is an emphatic “No.”

100. How do you help your parents?

That’s a good one to see if he is a good son.

101. Do you keep your promises?

Does anyone openly admit that they don’t?

102. Are you a natural leader, or do you feel uncomfortable in large groups?

Hey, someone has to play the lone wolf too.

103. What do you miss about being a kid?

This is a great question to get him to tell funny stories from his childhood.

104. What’s your favorite family tradition?

Whether it’s Christmas, Thanksgiving, or Sunday roast, we all have one.

105. What was the first thing you bought with your own money?

That should tell you a lot about his priorities in life.

106. What’s something you’ve never been good at?

Mental math? Small talk? We all have at least one.

107. Have you ever felt hopeless or like you want to give up on life?

What else would you do on a Monday morning?

108. What trait do you envy in others?

And why?

20 Deep Interesting Questions to Ask a Guy

Keep the conversation flowing with these interesting questions to ask a guy!

Here are 20 deep interesting questions to ask a guy:

109. Would you break the law to save a loved one?

Who wouldn’t?

110. Do you think crying is a sign of weakness or strength?

If he didn’t get the memo yet, let him know that it’s a sign of strength.

111. Which celebrity would you want to meet the most?

And what would you do when you met them?

112. What would you change about social media?

The ads? The privacy concerns? The fact that your most embarrassing pictures are out there for all the world to see? It’s hard to pick.

113. What food would you never eat?

Some people would happily eat insects but would never touch Brussels sprouts.

114. What’s the difference between living and existing?

That’s a real deep one.

115. Which superpower do you wish you had?

Why have just one?

116. Where do you think the most romantic vacation would be?

On the beach, in the mountains, on a city break, or somewhere else?

117. Do you think it’s important to keep up with the news?

We should keep up with world events. The challenge is not to get overwhelmed.

118. Do we have control over our lives?

Not entirely, but still a lot more than we think.

119. If you had to choose a career path for your children, what would it be?

Probably something boring — which is why you’d never let your parents choose your job for you.

120. If you could prevent any historical disaster, what would it be?

And how do you think that would have changed the course of history?

121. How do you handle people you don’t like?

You don’t.

122. What small stuff do you always sweat?

We all have our irrational obsessions with perfectly irrelevant stuff.

123. Do you care what others think about you?

If he says he isn’t, he is either lying or a psychopath.

124. What’s something that everyone looks stupid doing?

Trying to talk to babies, 100%.

125. Could you go for a month without any kind of electronic gadget?

Talking about a digital detox!

126. If you could make one absolute rule for a day that everyone should follow, what would it be?

The Golden Rule would make a good choice.

127. Who’s your favorite villain?

It could be fictional or a real-life one.

128. If you were a ghost, how would you haunt people?

We bet he’d come up with something funny.

12 Deep Questions to Ask Your Friends

We think we know our friends, and yet they keep surprising us. If you want to get to know them better, use these some awesome deep questions to ask your friends.

Here are 12 deep questions to ask your friends:

129. Are you holding onto something that you need to let go of?

You could try to help them out with that.

130. What emotion do you experience the most?

It’s not what you are thinking!

131. What do you want people to feel when they’re around you?

Calm? Joyful? Intrigued?

132. What’s the craziest thing that you’ve done with someone?

More importantly, can the two of you top that?

133. Are you still in touch with your childhood friends?

And if they aren’t — why not?

134. How long does it take you to trust someone?

They seem to be trusting you, which is all that matters.

135. Is it easy for you to show yourself love or speak kindly to yourself?

We are our harshest critics. Try not to be too hard on yourself today.

136. When have you felt your biggest adrenaline rush?

Well, that should be interesting!

137. If you got to choose your name, what would it be, and why?

The answer may surprise you! So many people just don’t like their names.

138. If you could use magic to do one mundane task for the rest of your life, what would it be?

Ours would be taking the garbage out.

139. What’s the weirdest item you keep by your bed?

Do you really want to know that about your friend?

140. What’s the strangest purchase you’ve made or almost made on Amazon?

You wouldn’t believe it even if you saw it.

141. Why is it a gift to have you as a friend?

You should be the one answering that question!

15 Deep Questions to Ask Yourself

We put so much effort into getting to know other people that we often forget about ourselves. That’s why a set of interesting questions to ask yourself is what you need. Some of the answers are sure to surprise you!

Here are 15 deep questions to ask yourself:

142. Is it more important to love or be loved?

No, you can’t pick both — that’s cheating.

143. Do I like who I am right now?

You really should. You may be a little rough around the edges (aren’t we all?), but you are still awesome!

144. When was the last time I laughed so hard?

If it’s been a minute, treat yourself to your favorite stand-up comedy or whatever it is that makes you laugh.

145. Why am I afraid of being true to myself when others are around?

Don’t worry; it’s perfectly normal.

146. Am I a servant of money?

There’s a lot more to life than money, so make sure to remind yourself of that daily.

147. When was the last time I extended kindness to somebody?

Make that today if you haven’t already! It could be something as simple as a genuine smile.

148. How meaningful is my life?

Immeasurably — and don’t let anyone and anything convince you otherwise.

149. What am I willing to go the extra mile for?

It better be your loved ones. If it’s not, you have some serious thinking to do.

150. Do I really listen when people talk to me?

You better. No one likes people who talk at you rather than to you.

151. When was the last time I tried something new?

Come one, live a little!

152. Do I often make excuses?

We all do from time to time — just don’t make a habit out of it.

153. Am I a good example for those around me?

Be the change you want to see in the world.

154. Do the people I around me add value to my life?

And do you add value to theirs?

155. When was the last time I did something nice for myself?

It better be today — you deserve it.

156. When was the last time I heard “I love you”?

And who said it?

7 Deep but Random Questions to Ask

If the conversation is a little on the dull side, spice it up with some random questions to ask people.

Here are 7 deep but random questions to ask:

157. What’s one fact about the universe that blows your mind?

How about that it exists in the first place?

158. Where would you like to move?

We all have our dream destinations.

159. What’s your favorite movie line?

You may want to note that down; it’s probably great.

160. If your life was a movie, what songs would be on the soundtrack?

Is it something romantic, epic, or laid back?

161. Are you romantic or a little naughty?

What? It’s always good to know — just in case.

162. How would you describe your perfect girl in five words?

And no, you can’t use “beautiful,” “sexy,” or “hot.”

163. What’s the most important file on your computer?

You might want to back that up if you haven’t already.

12 Deep Never Have I Ever Questions to Ask

In the mood for a round of never have I ever? Use these never have I ever questions to ask!

Here are 12 deep never have I ever questions to ask:

164. Never have I ever said “I love you” when I didn’t mean it.

Guilty as charged. We know better now, though.

165. Never have I ever smoked a joint.

What? It’s becoming legal in more and more places.

166. Never have I ever gotten in a physical fight.

Some people are just looking for trouble.

167. Never have I ever cried in public.

We all have — at least when we were babies.

168. Never have I ever skipped school.

Does pretending to be sick count?

169. Never have I ever dreamed of revenge for someone.

It’s probably okay as long as you don’t act on it.

170. Never have I ever manipulated someone.

Define “manipulation.” Does being extra nice to your waiter in order to get the best table count?

172. Never have I ever been up for more than 36 hours.

Who hasn’t pulled an all-nighter back in college?

173. Never have I ever needed my GPS while I was walking somewhere.

We are not judging — we’ve used one in our own neighborhood.

174. Never have I ever placed a large value on brand-name clothing.

All brand-name clothing is overpriced anyway.

175. Never have I ever been afraid to be home alone.

What? The house makes creepy sounds at night.

176. Never have I ever talked back to my parents.

Um, isn’t that what teenagers are supposed to do? Guess we got the wrong memo growing up.

12 Deep Would You Rather Questions

Dilemmas always make for good conversation, so we’ve collected this list of our favorite deep would you rather questions to help you spice up your talking game.

Here are 12 deep would you rather questions:

177. Would you rather find a dead body or witness a deadly assault?

This one is not for the faint-hearted.

178. When in a bad mood, would you rather be left alone or have someone cheer you up?

Depends on how bad of a mood you’re in.

179. Would you rather be able to change the future or the past, just by imagining it?

Hint: changing the past will also change the future (but not necessarily in the way you want!).

180. Would you rather have a child at the age of 20 or 40?

Age is just a number. What matters is that you love your kids and give them everything they need to thrive.

181. Would you rather be able to erase your or other people’s memories?

Temporarily erasing some of your friends’ memories would make for a great prank.

182. Would you rather have a lot of mediocre friends or one really good friend?

Is that even a question? One loyal friend is all you need to get through all life’s challenges.

183. Would you rather be born into a loving or a wealthy family?

How about a loving and wealthy family?

184. Would you rather be ignored or criticized?

Criticism is a form of attention, at least.

185. Would you rather know how the world began or how it ends?

If you know how it all ends, please, don’t tell us.

186. Would you rather be surrounded by people who brag all the time or who complain all the time?

Real tough choice. Both sound like complete narcissists to us.

187. Would you rather know everything about the universe or know the consequence of every choice you make?

In either case, you’d have a lot to think about.

188. Would you prefer fun at work or work for fun?

Is there a difference?

How to Pick the Best Deep Questions to Ask

Talking to guys can be challenging, to say the least. Follow these easy steps and you’ll be good to go!

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

1. Take a Deep Breath and Relax

Stress and anxiety are real conversation killers. For best results when talking to a guy, try to be as relaxed and calm as possible — and enjoy the moment. Everything else will flow from there.

2. Get Inspired from What You Already Know About Him

Use the information you already have about him to come up with relevant questions that may interest him.

3. Go with the Flow

Good conversations have a natural rhythm. Don’t try to force things, and go with the flow. It doesn’t matter if you don’t ask all the questions you had prepared as long as both of you end up having a good time.

More Awesome Ways To Get The Guy

Looking for more awesome tips to get the guy of your dreams?

  1. Read our guide on how to get a boy to like you.
  2. Check out our tips on how to tell if a guy likes you.
  3. Learn how to flirt with a guy.

Conclusion

You can get to know anyone or the guy you like better by asking these questions. Spark deeper connections by trying out some of our deep questions to ask!

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 Marriage.com, iHeart Media, Elite Daily, and The Urban List. Jasper lives in Georgia with his new bride.

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