Deep Questions To Ask

Having a conversation is one thing. Having a good discussion is another.

Questions are the best way to facilitate a meaningful debate and time together. They are also the building blocks of effective communication, and poor questions can be detrimental to any interaction.

These deep questions listed below act like seeds; they direct productivity and focus while creating new avenues for discussion. This is so simple and universal that it can be applied to almost any scenario with anyone.

By the way, you might also enjoy 200 Questions To Ask a Friend.

Deep questions to ask anyone

1.) What are your passions in life?

2.) If not now, then when?

3.) Do you celebrate the things you do have?

4.) What’s your most significant stressor right now?

5.) Who was your favorite cartoon character when you were a kid?

6.) What is the worst job you’ve ever had?

7.) What beliefs do you hold with which many people disagree?

8.) What do you think the solution is to climate change?

9.) What do you think of Artificial Intelligence? Do you find it scary or amazing?

10.) If you could change how people act or behave, would you want to do it?

11.) Have you ever had an epiphany? If so, what was it like for you?

12.) If you could have three wishes, what would they be?

Deep questions to ask friends

13.) What do I think about when you are alone?

14.) Is it possible to lie without saying a word?

15.) When was the last time you tried something new?

16.) What life lesson did you learn the hard way?

17.) Who do you sometimes compare yourself to?

18.) Does my presence add value to those around me?

19.) Do you think people can change?

20.) Are you still friends with anyone from high school?

21.) Are you very close to anyone in your family? Why?

22.) What type of music energizes you?

23.) Who was your favorite cartoon character when you were a kid?

You might like Never Have I Ever Questions.

Deep questions to ask about life

24.) What is the difference between living and existing?

25.) What would you regret not entirely doing, being, or having in your life?

26.) What did you learn early that people around you didn’t?

27.) Is stealing to feed a starving child wrong?

28.) Do you think your parents did a great job instilling good values in you?

29.) What is important enough to go to war over?

30.) What accomplishments are you most proud of?

31.) What single event has had the most significant impact on who you are?

32.) When you are 80, what will matter to you the most?

33.) If you had the opportunity to know when you would die, would you want to find out?

34.) What do you want people to remember about you after you’re gone?

35.) What does spirituality mean to you?

36.) Would you want to know the answer to life if someone could tell you?

37.) What’s one tragedy you hope never happens in your life?

See Romantic Questions To Ask a Guy.

Love conversation starters

38.) Who do you love, and what are you doing about it?

39.) Do you believe in love at first sight?

40.) What’s the importance of a connection between two people?

41.) Do you love yourself as much as you expect others to love you?

42.) When was the first time you said “I love you” to someone other than your family?

43.) How long do you think it takes to know you love someone?

44.) Why did your last relationship end?

45.) What’s something you used to believe about relationships but no longer do?

46.) Which would you like most: physical touch or quality time?

47.) What would be your perfect date night?

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

49.) Would you ever be able to live without the idea of friendships or love in life?

Deep questions to ask to get to know someone

50.) If you could live anywhere in the world, where would you live?

51.) What makes you smile?

52.) If you were a dog, what breed would you be?

53.) Are you a mountain or a beach person?

54.) What is the weirdest food combination you enjoy?

55.) What is your favorite workout?

56.) What superpowers did you wish you had when you were a kid?

57.) Have you ever shoplifted anything?

58.) Are you a morning or a night person?

59.) How comfortable are you talking about your feelings and with whom?

60.) What was the most intense experience you’ve had?

61.) Which activities make you lose track of time?

62.) What is your star sign? And do you believe in astrology?

See 125 Most Likely To Questions.

Deep questions to ask yourself

63.) What is a skill that you want to build?

64.) When was the last time I told myself, “I love you”?

65.) Are you proud of yourself?

66.) What do you think your pet thinks about you?

67.) What’s your best childhood memory?

68.) What’s the most sensible thing you’ve ever heard someone say?

69.) Why am I still in this job if I hate it?

70.) What does happiness look like to you today?

71.) Am I a better person today than I was yesterday?

72.) Do you ask enough questions or settle for what you know?

73.) What is your most important lesson this year?

74.) What was the most memorable experience from your childhood?

75.) If you had a friend who spoke to you the same way you sometimes talk to yourself, how long would you allow this person to be your friend?

76.) How positive are you about your body?

77.) What is one thing I could start doing today to improve the quality of my life?

78.) What negative thoughts do you have? How might you shift them to be more positive?

79.) How would you be different if raised in another family?

Best questions to ask a crush

80.) What do you wish you had spent more time doing five years ago?

81.) What would be the perfect amount of time each day you’d spend with your partner?

82.) What are some of your favorite books?

83.) When was the last time you heard the words “I love you?”

84.) What skills are people usually surprised you have?

85.) How do you react when you’re upset?

86.) What do you look for in a romantic partner?

87.) What question have you wanted to ask me?

88.) How private are you? Do you like posting everything on social media?

89.) What is your dream vacation?

90.) Do you prefer indoor or outdoor activities?

91.) What’s a deal-breaker for you in a relationship?

Deep questions to ask your partner

92.) How do you relax when you’re stressed out?

93.) What can you do today that you could not doof a year ago?

94.) What’s the weirdest dream you’ve ever had?

95.) What song would you want at your funeral?

96.) Would you like to know the secrets of all people if you could?

97.) Do you usually stay friends with your exes?

98.) Who inspires you the most in this world?

99.) Which one of your ex-girlfriends or ex-boyfriends has truly defined you going forward?

100.) Who was your first crush, and what were they like?

101.) Have you ever told a lie that you regretted?

102.) Have you ever done something you regretted?

103.) What secret fear did you have as a kid that you now realize was ridiculous?

Deep questions to ask your boyfriend

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

105.) What’s something you wish your friends and family understood about you?

106.) How would you describe me to your friends?

107.) What did you like about me when you first met me?

108.) Who would win in a fight between Superman and Batman?

109.) How have I changed since we started dating?

110.) Would you rather have intelligence over looks?

111.) Have you ever cried in public? What happened?

112.) What are your coworkers like? Are you friends with any of them?

113.) How did you know you loved me?

114.) What’s one thing I don’t already know about you?

115.) How do you build friendships with other guys?

116.) Which villain do you secretly admire? Why?

117.) What was the most important lesson you’ve learned from a past relationship?

Deep questions to ask your girlfriend

118.) Have you ever had your heart broken? What did it feel like to you?

119.) Have you ever asked a guy out on a date?

120.) Which parent are you closer to and why?

121.) Can you cook me your favorite meal?

122.) Who is that one person you can talk to about just anything?

123.) How have your parents impacted your view of love and relationships?

124.) Would you go back and invent social media over again?

125.) What movie made you cry the hardest?

126.) What does your perfect vacation look like?

127.) What are some of the cultural pressures that people put on you as a woman?

128.) If you could change one decision you made when you were younger, what would it be and why?

Deep questions to ask your ex-boyfriend

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

130.) What would you do differently if you knew nobody would judge you?

131.) What do you think leads people to cheat in relationships?

132.) Am I holding onto something I need to let go of?

133.) What’s something you value about your self-image?

134.) When was the last time you said “I love you” to me and meant it?

135.) What do most women love that you just don’t care about?

136.) Would you ever take back someone who cheated?

137.) Have you ever written a song or poem about me?

138.) Do you think once you love someone, you will ALWAYS love them? Or do you think love can fade away with time?

139.) Do you ever make excuses for your bad behavior?

140.) If you could change one thing about yourself, what would it be?

141.) Do you think anyone can cheat, or only cheaters cheat?

142.) What was the biggest lesson from our breakup?

Fun questions to ask people

143.) Imagine you lived in a society without money. Would it be a better or worse society?

144.) When was the last time you listened to the sound of your breathing?

145.) If you could instill one piece of advice in a newborn baby’s mind, what advice would you give?

146.) What would you be if you had to wear one Halloween costume every day for the rest of your life?

147.) What’s the worst color that was ever invented?

148.) What is the worst TV advertisement you’ve seen recently?

149.) What song would make the best theme music for your life?

150.) What is your favorite sleeping position of all time?

151.) What was the weirdest conversation you overheard?

152.) Which instrument has the funniest sound?

153.) If animals could talk, which would be the rudest?

154.) Which word would you use if you could only use one for the rest of your life?

155.) If “hello” were to be replaced by another word as a greeting, what word would that be?

156.) If you could live inside any movie, what movie would it be?

Questions for colleagues

157.) Do you love working from home or in the office? Is there a balance of both that you like best?

158.) Do you collect anything?

159.) Do you have houseplants in your office?

160.) What’s your favorite word?

161.) Where do you work most frequently from at home? Your office? Your kitchen table? The backyard? Your bed?

162.) What’s one thing you’re learning now or learned recently?

163.) Who inspired you to pursue the career you have today?

164.) What’s the worst job you’ve ever had, and what did you learn from it?

165.) Which movie have you seen recently, or what are you watching on Netflix?

166.) Who would it be if you could meet any person, living or not?

167.) What did you want to be when you grew up?

168.) What drains you at work?

169.) What’s the most significant misconception people have about your position?

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

171.) Who has been the most significant influence in your life?

172.) What is your life philosophy?

173.) What would it be if you could go back in time and change one thing?

Deep Questions FAQs

Here are some frequently asked questions about deep questions.

Final Thoughts

As you can see, there are a lot of different questions you can ask in design. It all depends on what your goal is. Finding the right questions can help you start a conversation and build a better understanding with anyone.

This list isn’t necessarily a blueprint you need and comes to every meeting. All you have to do is genuinely listen and connect to whom you talk.

By Sara Thomas

Sara is a writer based in St. Paul, Minnesota.

Etcetera

You are on our Deep Questions To Ask page.

You might also like the following:

This or That Questions

Truth or Dare Questions for Friends

Hard Trick Questions