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750+ Deep Questions To Ask If You Really Want To Get To Know Someone

Filed in Articles by on June 23, 2021

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It has been said many times, that the best way to learn and to get information is to ask questions? This seems to be a very credible statement as one can learn virtually anything from simply knowing deep questions to ask. Certainly, knowing deep questions to ask will give you the opportunity to access whatever information you need about a person or a situation.

Deep Questions to Ask Your Friends

Honestly, it is difficult to completely know a person or even yourself very well. Selecting some deep questions to ask yourself and any other person will afford you a better perspective and idea about your personality and that of others. Interestingly, people ask questions all the time. Unfortunately, many times they ask the wrong questions.

Evidently, to get the right answers, you need to ask the right questions. Thus, this calls for having the knowledge of deep questions to ask.  In this article, you will be able to find really deep questions to ask anyone and yourself too.

Deep Questions to Ask Your Friends

It is just too necessary to know who you call your friend on a deep level.  For this reason and other critical ones, you need to have deep questions to ask them. Consider these questions below.

1.  If you died tonight, what would you regret not doing?

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

3. Do you believe in life after death, and why?

4. Do you like who you are now?

5. When was the last time you laughed so hard? “Deep Questions to Ask a Friend”

6. Would you relocate to a place where you don’t have any family or friends?

7. What secret trait do you wish that people know about you?

8. What is your personal philosophy in life?

9. Do you consider yourself spiritual or religious?

10. If all your wishes were granted today, how would you describe your life five years from now?

11. What is your worst memory of elementary school?

12. Are you close to your parents, and why?

13. Do you prefer looks or brains?

14. What is your best childhood memory?

15. What’s the one trait or personality you’d like to change about yourself?

16. Do you consider yourself an introvert or an extrovert?

17. What book and movie spoke to you, and in what way?

18. Are you assertive or a pushover?

19. What is your major turnoff in a romantic relationship?

20. Would you do a crazy thing for a friend?

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

22. Do you believe that the present is really better than the past?

23. Have you seen an extreme example of poverty, and if so, how would you describe it?

24. What realities or truths are you in denial about?

25. Do you feel that you’re making a difference with the way you live your life?

26. Are you willing to share your password with your romantic partner, and why?

27. How do you feel about a cheating partner?

28. At what age do you think people should get married?

29. Do you think you will be a great parent, and why?

30. What would you do if your parents did not approve of your partner?

31. Do you believe that people of the opposite sex can be the best of friends?

32. Have you ever lost someone who’s very close to you?

33. Who is the person with whom you can talk about anything?

34. Do you believe in burning bridges when it comes to exes?

35. Do you prefer someone cheering you up, or being left alone when you’re in a foul mood?

36. How judgmental are you?

37. What is your description of a perfect weekend?

38. Have you broken someone’s heart recently?

39. Are you willing to relocate for love?

40. Do you keep a journal, and if yes, how often do you write in it?

41. What are the top five things you are grateful for? (Here are 120 gratitude prompts you can use during this type of conversation.)

42. Do you think that cheating partners should be given a second chance?

43. What do people constantly misunderstand about you?

44. How would you describe your perfect vacation?

45. What are the two greatest lessons you’ve learned from a past relationship?

46. Do you think that people can find true love online?

47. Do you regret anything in life?

48. What are three things that are on your bucket list?

49. What excites you the most?

50. When you’re alone, what do you usually think of?

51. How meaningful is your life?

52. What gives your life meaning?

53. What would your three wishes be if someone could make them come true?

54. Are you willing to lay down your life for someone, and who is it?

55. What top five lessons have you learned the hard way?

56. Do you believe in magic or in science? “Deep Questions to Ask a Friend”

57. What would the world be like if you hadn’t been born?

58. What is your definition of fame?

59. Do you wish to be famous?

60. What would you want to be famous for?

61. What is the greatest invention of this age?

62. Would you be willing to go the extra mile for something or someone?

63. Which one wins: reality or imagination?

64. When was the last time you said “I love you” to your parents?

65. Who do you look up to in life?

66. Do you give advice to others, and why?

67. Which is the better option: being a heartbreaker or being heartbroken?

68. f you could swap lives with someone for a day, who would you choose and why?

69. Which emotion best represents you, and why?

70. What do you think will bring about humanity’s extinction?

71. Do you feel happy when you use social media?

72. Will you encourage the younger generation to use social media?

73. If you had a billion dollars, how would you use the money to benefit the less privileged?

74. Which one is a better situation: broke or lonely?

75. When you die, would you prefer to be alone or surrounded by people you know?

76. What’s the lowest point in your life this year?

77. What’s the highest point you’ve experienced in your life this year?

78. Who’s hiding behind the mask you present to the world?

79. Is your life going in the direction you want?

80. If your life was a movie, what would the title be and why?

81. Have you experienced any miracle in your life?

82. Does art have any significance in society?

83. On a scale of 1 to 10, how fulfilled are you about life?

84. When was the last time you were moved to tears by a movie?

85. How do you define “a life well lived?”

86. What regrets would you have if you were to die today?

87. Can humans avoid being in love?

88. Is there such a thing as absolute freedom?

89. If you were given free rein to design the ideal metropolis, what would your city be like?

90. Is there such a thing as lasting peace?

91. Do you approve of stealing from the rich to give to the poor?

92. Do you believe that each one of us has a special mission in life?

Queries to Self

Deep Personal Questions to Ask Yourself about Life

As life goes on, you may start doubting your own very self and even the things you stand for. At this point, the best thing to do is to ask reflective questions. Thus, you need deep questions to ask yourself like the ones below.

1. What’s on your bucket list this year?

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

3. How do you feel about sharing your password with your partner?

4. What is the craziest thing you’ve ever done and would you do it again?

5. If a genie granted you 3 wishes right now, what would you wish for?

6. What’s your biggest regret in life?

7. What’s the one thing that people always misunderstand about you?

8. Are you confrontational?

9. If you could change one thing about yourself what would it be?

10. Do you judge a book by its cover?

11. What makes you feel accomplished?

12. When was the last time you broke someone’s heart?

13. What is your greatest fear?

14. Who was your favorite teacher and why?

15. What was the worst phase in your life?

16. Would you relocate for love?

17. What’s your philosophy in life?

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

19. What accomplishment are you most proud of?

20. What’s your favorite hobby to do alone?

21. Did you ever write a journal?”Deep Questions to Ask a Yourself”

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

23. What did your past relationship teach you?

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

25. Which parent are you closer to and why?

26. What was the best phase in your life?

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

28. Who are five people you are closest to?

29. Do you believe in second chances?

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

31. Have you ever lost someone close to you?

32. If you are in a bad mood, do you prefer to be left alone or have someone to cheer you up?

33. What’s the most exciting thing that’s happened this past year?

34. When have you felt your biggest adrenaline rush?

35. What is your idea of a perfect vacation?

36. What’s one thing that bothers you most about the world today?

37. Are you religious or spiritual?

38. Would you ever take back someone who cheated?

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

40.Do you consider yourself an introvert or an extrovert?

41. What’s your favorite book/movie of all time and why did it speak to you so much?

42. Are you more into looks or brains?

43. What’s the one thing you would like to change about yourself?

44.  Do I like who I am right now?

45. the hen was the last time I laughed so hard?

46. Have I done something recently that I could be proud of?

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

48. Must I take other people’s advice?

49. What annoys me the most?

50. Do others find me likable? (These social habits can make you more likable.)

51. When was the last time I fell head over heels with life?

52. Am I enriching other people’s lives with what I do?

53. How meaningful is my life?

54. What makes life meaningful?

55. Would I lay down my life for somebody?

56. How much money would I be willing to give to those in need if I won the lottery?

57. What is the day that I would like to live over and over is

58. Am I worthy of being loved?

59. If I had not been born, what would be different about the world?

60. What were the three important lessons that I should have learned 10 years ago?

61. If I could tell my 18-year-old self one thing, it would be?

62. If my life was made into a movie, the title would be?

63. Would I enjoy watching a movie made of my life?

64. Is my definition of success the same as everyone else’s?

65. Do I have a personal mission?

66. How would I describe the perfect day?

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

68. What are my top five negative habits that I must change to something better?

69. Who do I look up to?

70. What outstanding qualities should my best friend have?

71. When was the last time I told someone I love him/her?

72. Am I satisfied with the quality of my romantic relationship?

73. When have I compromised my personal beliefs because I was afraid to be left out?

74. What skill do I possess that I can do better than others?

75. How often have I said yes when I wanted to say no?

76. What important lesson have I learned this week?

77. What three words would my friends use to describe me to strangers?

78. Have I intentionally broken someone’s heart?

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

80. What surprised me about myself this week?

81. How many hours have I been spending on the Internet?

82. Do I engage in negative self-talk?

83. Am I living a simple or complicated life?

84. How can I simplify my life? “Deep Questions to Ask a Yourself”

85. Are there things that I should have done when I was younger that I can no longer do now?

86. What would I change if I were the most influential person in the world?

87. When was the last time I kept in touch with my family, and for how long was it?

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

89. What stresses me out the most?

90. How can I make my life easier?

91. When was the last time I gave something without expecting anything in return?

92. What is the most challenging experience I’ve overcome in the last five years?

93. Am I spending enough time doing the most important thing in my life?

94. What message can I share with the rest of the world?

95. How easily do I get discouraged?

96. What was it that I never told someone and still regret not telling them?

97. How assertive am I?

98. How old or young do I feel inside?

99. Do I resent others whenever I give in to their wishes?

100. What am I holding on to that I need to let go of?

101. If I were given an envelope containing the date of my death, would I open it?

102. Who among the people I know bring out the best in me?

103. Do I often make excuses?

104. What would I ask for if one of my wishes would come true?

105. Have I matured because of challenges or because of the enjoyable moments in my life?

106. Would I ever choose the easy way in life?

107. What’s standing between me and my greatest dream?

108. Where will I be five in years?

109. When was the last time I was furious?

110. What can I do to make a difference in people’s lives?

111. If failures are the best teachers, why is it so bad to fail?

112. Is it wrong to steal in order to feed a starving child?

113. What should I spend more time doing?

114. Am I missing someone today?

115. What mistake will I never make again?

116. How do I make the most out of life?

117. When was the last time I gave up on something that meant so much to me?

118. Who are the people I truly love, and what am I doing for them?

119. Do I ask questions, or am I content with what I know in life right now?

120. Would I be happy if I never had to work again?

121. Where do I find inspiration?

122. What can’t I live without?

123. Can I live without money, or without love?

124. When was the last time I lost track of time while doing something?

125. What was that activity?

126. How do I want people to describe me at my funeral?

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Questions to Ask Kids

You can also take out time to chat with kids. Kids these days are very unpredictable. As such, you need to know deep questions to ask them too.

1. Can you remember the last time you laughed so hard, you snorted?

2. How do you eat an Oreo?

3. What is your favorite letter of the alphabet?

4. Would you rather have to scream or whisper?

5. Do you have a favorite chore you like to help with around the house?

6. What is your favorite movie? Actor?

7. Would you visit the moon for one day if you could?

8. What is your perfect dessert?

9. Do you like board games? Which ones are your favorite?

10. When was the last time you had the best day ever?

Deep Questions You can Ask Know Someone

Virtually everyone can be made to share a little of themselves.  when the question is right, the reply will be forthcoming. Get yourself familiar with these deep questions to ask anyone you meet.

1. What’s the most spontaneous thing you’ve done lately?

2. What two radio stations do you listen to in the car the most?

3. If you could hire someone to help you, would it be with cleaning, cooking, or yard work?

4. Would you rather vacation in Mexico or Alaska, and why?

5. What is your favorite thing about your career?

6. If you could live anywhere, where would it be?

7. Who is your hero?

8. If you could choose to do anything for a day, what would it be?

9. What is the best gift you have been given?

10. What really makes you angry? “Deep Questions to Ask a Someone”

11. If you could choose to do anything for a day, what would it be?

12. Would you rather win the lottery or work at the perfect job? And why?

13. Have you ever had a nickname? What is it?

14. What would you do if you won the lottery?

15. Do you like or dislike surprises? Why or why not?

16. Would you rather ride a bike, ride a horse, or drive a car?

17.  In the evening, would you rather play a game, visit a relative, watch a movie, or read?

18. What is your favorite game or sport to watch and play?

19. If you could only eat one meal for the rest of your life, what would it be?

20. Who is your favorite author?

21. What is your favorite family vacation?

22. What is your biggest complaint about your job?

23. Which would you rather do: wash dishes, mow the lawn, clean the bathroom, or vacuum the house?

24. What is your proudest accomplishment?

25. Would you rather win the lottery or work at the perfect job? And why?

26. What’s your favorite zoo animal?

27. What makes you laugh the most?

28. Who would you want to be stranded with on a deserted island?

29. If you could go back in time to change one thing, what would it be?

30. If you could share a meal with any 4 individuals, living or dead, who would they be?

31. How many pillows do you sleep with?

32. What’s the longest you’ve gone without sleep (and why)?

33. What’s the tallest building you’ve been to the top in?

34. Where do you see yourself in five years?

35. List two pet peeves. Aside from necessities, what one thing could you not go a day without?

36. How would your friends describe you?

37. What would you sing at Karaoke night?

38. What is the worst gift you have received?

General Get to Know You Questions

General Get to Know You Questions

If you are meeting with anyone or a stranger some time, you might get talking and it might just be wise to ask him or her some deep general questions. Thus, you have below really deep questions to ask anyone any time.

1. What’s the spiciest thing you’ve eaten? Would you ever eat it again?

2. What unnecessary products or services do you consider necessary?

3. Which fictional villain made you feel real hatred towards them?

4. What habit do you have that you think not many other people have?

5. How often is your brain on autopilot?

6. What’s the grossest thing you’ve drunk?

7. If colors had a taste, what would each color taste like?

8. What names were ruined for you because you knew someone terrible with that name?

9. What’s the best conspiracy theory you can make up on the spot?

10. How often do you feel utterly worn down?

11. What gross and unhygienic things do people do that bother you?

12. What was the best thing about how your parents raised you?

13. Where is the craziest place you have danced?

14. If when you died, you got put into a room for eternity with people who died the same way, how would you want to die?

15. What would an amusement park filled with your biggest fears be like? What rides would it have?

16. If jobs/careers had slogans what would be some of their slogans?

17. What do people really need to chill out about?

18. What are the two biggest lessons you’ve learned from previous relationships?

19. Why do you think we dream?

20. If you could switch genders for a length of time of your choosing, would you? And if so, how long?

21. What inedible thing do you wish you could eat?

22. Which hairstyles fit with which personalities?

23. If you could choose the next president of the United States, who would it be?

24. What’s the most stress-relieving thing you can get/do for less than 20$?

25. What’s something you wish you had never learned how it was made or how it works?

26. If you were forced into a dance competition, what song would you choose to dance to?

27. How would the world change if health potions existed?

28. How do you feel about God?

29. What scrambles your brain every time you think about it?

30. What’s the weirdest wrong number text or phone call you’ve gotten?

31. What would be the absolute perfect day?

32. What’s a lame joke you use on a regular basis?

33. If you could change your first name, what would be the most epic name you could choose?

34. What do you think aliens would actually look/be like?

35. Should toilet paper hang over or under?

36. How often do you go into a room and forget why you went into the room?

37. Do you like or dislike surprises? Why or why not?

Classic Questions to Ask a Man

Classic Questions to Ask a Man

Some men can be so uptight and reserved. Thus to get them to open up and talk, you need to ask them some deep and profound questions. You can get ideas of deep questions to ask a man below. 

1.  What was your childhood like?

2. Did you have a close bond with your parents?

3. Do you have any brothers or sisters?

4. What was your first crush like?

5. Are you still friends with your exes?

6. If you had to describe your father, what would you tell me about him?

7. What was your biggest achievement?

8. Do you like animals?

9. What’s your favorite song from your teenage years?

10. What makes you feel happy?

11. Are you a competitive person?

12. Do you like any sports?

13. What’s your favorite book?

14. Would you lend it to me?

15. What do you think about death?

16. What about children?

17. What is your favorite memory from childhood?

18. What is your favorite scent?

19. How did you lose your virginity?

20. What’s your strongest character trait?

21. What is your weakest spot?

22. Do you consider getting married one day?

23. How do you like to dance?

24. What is your favorite album?

25. What was the worst winter of your life?

26. On a scale from 1 to 10, how good would you say you are at singing in public?

27. Are you left-wing or right-wing? Or in between?

28. Are you pro-choice or pro-life?

29. What’s the most important quality you enjoy in a friend?

30. Have you ever felt attracted to a queer person?

31. Did you ever participate in a protest?

32. Would you date two girls on the same day?

33. Would you ever date a blind person?

34. Tell me about the one who got away.

35. How many pairs of shoes do you have?

36. Do you own a suit?

37. Have you ever stalked someone?

38. What’s the biggest life lesson you have learned?

39. What’s the most significant love lesson you have learned?

40. What is your favorite summer memory?

41. What is it about us girls that makes you so horny?

42. What was the biggest letdown of your life?

43. What would you take with you on a deserted island?

44. What would you say about your relationship with God?

45. What would you change about social media?

46. What is one thing a woman can do to instantly impress you?

47. What has been your most embarrassing moment so far?

48. What is one thing a woman can do that would instantly turn you off?

49. What is your favorite compliment to receive?

50. What makes you smile even when you’ve had the worst day?

51. Would you rather own dogs or cats for the rest of your life?

52. Tell me something you’ve never told anyone else.

53. What was your favorite candy or treat as a kid?

54. What food would you never eat?

55. What do you think your best physical feature is?

56. What do you like the most about me?

57. If you could change your job right now, what would you be?

58. Give them three words you would use to describe yourself.

59. What does your perfect date look like?

60. What is the coolest vacation you’ve ever taken?

61. Name one country you really want to visit. 

62. Would you rather go camping or clubbing?

63. What are you most afraid of?

64. What’s the nicest thing you’ve ever done for a woman?

65. What’s the nicest thing a woman has ever done for you?

66. What is your biggest dating dealbreaker?

67. What’s your earliest childhood memory?

68. What is one thing that always makes you angry?

69. What has been your greatest achievement so far?


Personal Questions to Ask a Man

If you wish to go deeper into the life of a man, you need to be mindful of the kind of questions you ask. Certainly, you would not wish to be misunderstood as being too forward. Therefore, you need to check the kind of deep questions to ask a man about some personal details.

70. What is one thing you love about where you live?

71. What is one thing you hate about where you live?

72. What’s your go-to Starbucks order?

73. If you could get one gift, what would it be?

74. Do you prefer to get a gift or gift cards or money?

75. Would you describe yourself as more of an introvert or an extrovert?

76. If you could re-do one moment in your life, what would it be?

77. Where is your favorite place to go when you need to relax?

78. Do you like going to the gym or working out at home?

79. What was the last thing that made you cry?

80. What’s something a woman could do that you could never forgive her for?

81. Have you ever been betrayed by a friend?

82. What’s your favorite thing about your friends?

83. How did you meet your best friend?

84. What question do you always ask women on a first date?

85. Do you want kids?

86. What makes you want kids?

87. What’s the most trouble you’ve ever been in?

88. Would you rather vacation at the beach or in a cool city?

89. What’s your dream car?

90. What’s your favorite book?

 91. What’s the worst movie you’ve ever seen?

 92. Which superpower do you wish you had?

 93. What’s the most fun thing you’ve ever done with your friends?

94. Are you closer to your mom or dad?

95. Who is your favorite family member?

96. What kind of extra-curricular activities did you do for fun in high school?

97. What’s your weirdest pet peeve?

98. Which is better: asking for permission or asking for forgiveness?

99. What would you do if you inherited 1 million dollars tomorrow?

100. What’s the most embarrassing moment of your life so far?

What is?

More Unique Questions

You can still go ahead and gather more information about a man with these unique and deep questions to ask a man. 

101. What fictional character do you identify with the most

102. Are you a superstitious type of person? About what?

103. Where would you rather live – a big house in the suburbs or a tiny apartment in a great location in the city?

104. If you could have any job in the world, what would it be?

 105. Ever have any trouble with the law or get arrested?

106. Do you think it’s important to keep up with the news or do you not care?

107. What’s the nicest thing you’ve ever heard about yourself? What do you WANT to hear about yourself?

108. What do you want to have going on in your life in 5 years, or 10, or 15?

109. Which would you rather be, smart or happy, and why?

110. You can have one superpower – and only one. What is it, and why did you pick it?

111. What’s your biggest regret that you have in your life so far?

112. Which show on TV do you absolutely HAVE to watch live when it airs?

113. When did you have your first kiss and who was it with?

114. If you were a waiter and a customer was a JERK, would you spit in their food?

115. What’s your favorite food to eat?

116. What’s type of music do you listen to?

117. What’s the one movie you love more than any other?

118. If you could only eat one food for the rest of your life, what would it be?

119. What’s the funniest thing that’s ever happened to you?

120. Has anyone ever walked in on you naked?

121. How do you deal with people in your life that you don’t like?

122. What’s the funniest thing that happened in your childhood?

123. Do you like waking up early or staying up late?

124. What are you most afraid of?

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

126. Guess – what am I thinking about right now? 

127.  If you had to give me a nickname right now on the spot, what would it be?

128. Do you think it’s possible that we met in a previous life?

129. Pick one to live in: beach, city, or country?

130. How would you describe me to someone who doesn’t know me?

131. Which describes your personality… naughty or nice?

132. What’s the sexiest animal in the animal kingdom?

133. Who’s a celebrity you have a crush on?

134. You get to date one celebrity – who is it?

135. If you had the power to read someone’s mind, whose would it be?

136. What would you do in a week if you were told you only had a week to live?

137. Did you ever cheat on a test in school?

138. Do you feel like something is missing from your life?

139. What are you most passionate about?

140. What is one thing you’d love to learn more about?

141.  What is your favorite non-physical part about yourself?

142. What is more important to you: money or happiness?

143. What is your biggest pet peeve?

144. What was the last thing to make you cry?

145. What is the craziest thing you’ve ever done?

Interesting Questions to Ask a Lady

Thrilling and Deep Questions to Ask a Lady

This is another set of a complicated set of creatures. Ladies have many intricacies in addition to their natural disposition. Knowing the kind of deep questions to ask a lady is just too important. Ladies are just too sensitive and would not wish for your questions to annoy her.

1. What is the most romantic trip you dream of going on?

2. Which song comes to your mind and heart, while you think of me?

3. What is the best thing you like about me?

4. What is the best true love story you have ever heard?

5. When did you first fall in love with me?

6. What nickname/pet name you would call me lovingly by?

7. Is there such a thing as being too much in love?

8. What is your idea of the perfect romantic gift?

9. Which trait of mine first drew you to me? What is your favorite trait of mine now?

10. If you saw me out somewhere with another woman, would you think she was a relative, an old friend, or a girl I’m seeing on the side?

11. What did you think about me when you first saw me?

12. Can you share something from your life that you’ve never shared with anyone else?

13. What were you feeling when we had our first kiss? 

14. What is the one thing about our relationship that makes you most happy?

15. Do you prefer a good conversation or good sex?

16. Do you think you’ll ever want to settle down and have kids?

17. Do you prefer a good hug or a good kiss?

18. What’s your perfect date?

19. What’s the most romantic movie you’ve ever seen?

20. What’s the best thing about being in a relationship?

21. Can you share a secret about what you find attractive that you haven’t shared with anyone else?

22. If you could nickname me ice cream, what ice cream would it be?

23. What’s the most important trait for a romantic relationship to be successful?

24. Is communication more important than sex in a relationship?

25. What’s the one thing about a relationship that makes you most happy?

26. What are your feelings about our first kiss?

27. What are the memories between us that you cherish the most?

28. What is your dream honeymoon?

29. Do you want to have a big wedding? Or a small one just for those close to you?

30. Do you prefer a passionate kiss? Or a long, warm hug?

31. What’s the sexiest dream you’ve ever had?

32. Would you prefer love on a sandy beach or in the beach water?

33. What’s the most romantic date you’ve ever been on?

34. What’s your favorite romantic song?

35. Do you like hearing how beautiful you are?

36. If I could take you to any place in the world right now, where would you want to go?

37. Guess what I like about you most.

38. How do you like a guy to show his feelings?

39. Describe making love in three adjectives.

40. What’s your favorite thing about making love?

Personal and Deep Questions to Ask a Lady

Are you sewing for finite details about the lady, no need to beat about the bush? With comely and deep questions to ask a lady, you will get exactly what you need.

41. What are the qualities that you are looking for in a man?

42. When you were younger, what did you want to be when you grew up?

43. Do you think that you would be happiest living in a city or on a farm?

44. Do you pay attention to politics or do you tend to stay away from that?

45. What was/is your favorite subject in school?

46. Do you believe that the saying “nice guys finish last” has any truth to it?

47. What is your favorite type of music?

48. What is your dream car?

49. Do you care more about making money or pursuing happiness?

50. What is your favorite color?

51. What’s your philosophy in life? “Questions to ask a Girl”

52. If there’s one thing you could change about yourself, what would it be?

53. Would you consider yourself spiritual or religious?

54. Are you an introvert or extrovert?

55. What was your best phase in life?

56. What’s your favorite movie of all time?

57. If you could go back in time and give yourself advice, what would you say?

58. Do you care more about looks or brains?

59. If you’re in a bad mood, do you want someone to cheer you up, or do you prefer to be left alone?

60. What’s the perfect weekend for you?

61. What’s something you believe to be true that most people don’t believe?

62. What’s your most important quality in a friend?

63. Have you ever broken someone’s heart?

64. Do you prefer to be friends with introverts or extroverts?

65. What decade do you think you would most fit in? “Questions to ask a Girl”

66. Are you close to your family?

67. What is one activity where you feel most like yourself?

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

69. If you had one week to live, what would you do?

70. What is the real story behind your last Instagram post?

71. Would you rather be rich and famous or rich without fame?

72. When you read the newspaper, what section do you skip to immediately?

73. Are you superstitious?

74. If you could be a fictional superhero, what would you be?

75. Do you prefer big parties or small gatherings?

76. What’s something that happened in your past that you’re incredibly embarrassed about?

77. If you could be incredibly skilled at one thing, what would it be?

78. Are you a mountain or beach person?

79. Would you rather be in love or be rich?

Interesting Questions to Ask a Lady

Interesting Deep Questions to Ask a Lady

81. What’s one thing you’ve done, but will never end up doing again?

82. What’s the best present or gift you’ve ever received from someone?

83. If you could live anywhere in the world, where would it be? “Questions to ask a Girl”

84. What is your favorite and most treasured memory?

85. In four minutes, tell me your life’s story.

86. What or things or person has influenced you the most?

87. Who do you think knows you the best?

88. What’s your favorite childhood memory?

89. What’s the nicest thing someone could genuinely say about you?

90. If you had unlimited money, what would you do with it?

91. Can you speak in any foreign languages? If yes, can you show me?

92. What’s your dream career?

93. What’s one thing on your bucket list?

94. Are there any places you would love to travel to?

95. What is your greatest accomplishment?

96. Would you rather live in a small house with an amazing view, or a massive mansion in a subdivision?

97. Would you like to be famous, if so, in what way?

98. If tomorrow you woke up with new quality, talent or ability, what would you like it to be?

99. If your house caught on fire, what would be one thing you would have to save first?

100. What’s your most terrible memory that you’d love to forget about?

101. If you could have dinner with anyone in the world, past or present, who would you choose?

102. What skill would you like to become a master at?

103. If you could play the role in any movie, what person would you want to be?

104. What’s your favorite photograph of yourself?

105. What’s one thing you’ve learned that most people don’t know how to do?

106. How do you spend your free time, and where do you like to go?

107. What is one thing you were afraid to do but felt amazing after you accomplished it?

108. What role models do you respect the most?

109. What about yourself, do you find the most pride in?

110. What’s your favorite place in the world?

111. What’s your biggest fear?

112. What’s the weirdest thing you’ve ever bought?

113. If you could only own a few things, what would they be?

114. What’s your biggest regret

115. What’s your favorite memory?

116. If you could pick one, would you rather have infinite money or love?

117. If you could undo anything from the past, what would it be?

118. What celebrity would you switch lives with?

119. What would you change about yourself?

120. If you were able to see in the future, what would you tell yourself or want to know?

121. What in life are you the most grateful for?

122. What’s your ultimate goal in life?

123. If you could go back in time, what would you want to change?

124. What’s the best piece of advice you’ve ever received from someone?

125. What has inspired you recently?

Cute and Deep Questions to Ask a Lady

Do you want your heart to blush while replying to you? Thrill her with these deep questions to ask a girl.

126. Which do you like better: sunrise or sunset?

127. When you were a kid, what did you imagine your life would be like as an adult?

128. What is your favorite playground game?

129. What movie can you quote the most lines from?

130. Has anyone ever thrown you a surprise party?

131. What is your idea of the perfect birthday?

132. What is the best way to wake up?

133. How do you treat yourself?

134. Have you ever received a random act of kindness?

135. What is your favorite children’s book?

136. What is your favorite home-cooked meal?

137. Who was the best teacher you ever had?

138. What was your favorite toy as a kid?

139. What is the oddest thing you have kept for sentimental reasons?

140. Who do you call when you need advice?

141. What sounds or smells bring you comfort?

142. Which do you like better: giving or receiving gifts?

143. What is the best compliment you have ever received?

144. What do you look forward to the most when you think about getting old?

145. Do you daydream?

Random Questions

146. Would you ever enter a hot dog eating contest?

147. What bar competition would you win? (Darts, peanut toss, pool, etc.)

148. Can you juggle?

149. If you had to give up chocolate, wine, or coffee, which would you choose?

150. Have you ever been hit on by a woman? “Questions to ask a Girl”

151. What is the weirdest thing you’ve ever eaten?

152. Have you ever had déjà vu?

153. Do you remember your dreams?

154. What unhealthy food do you wish was good for you?

155. What’s the best magic trick you’ve ever seen?

156. Have you ever been hypnotized?

157. If you could steal the talent or intelligence from any one person, whose would you steal?

158. Besides social networking sites, what websites do you visit every day?

159. Would you ever be a Sugar Baby?

160. Did your parents ever ground you?

161. Have you ever seen a ghost?

162. Do you like having your picture taken?

163. Would you ever pose nude for a photograph or painting?

164. What do you like most about being a woman?

Innovative Mind

More Personal Questions

165. What is the real story behind the last Instagram picture you posted?

166. Do you screenshot the sweet texts that people send you? What is the last one you’ve received?

167. If you competed on a game show, which charity would you play for?

168. What is the last thing you wrote by hand instead of typed?

169. Which song do you always end up playing during long drives?

170. If you had to guess, what color is your aura?

171. Do you know your love language?

172. Which romantic gesture do you believe is overrated?

173. What small act of kindness do you believe is underrated? “Questions to ask a Girl”

174. Which piece of makeup gives you the most confidence?

175. What is the one compliment that people always seem to give you?

176. When was the last time you gave someone a second chance?

177. What is something you wish more people knew about you?

178. Do you hope to grow up to become more like your mother or your father?

179. What has changed the most about you since graduating high school?

180. Which milestone are you most proud of reaching thus far?

181. When was the last time you complimented a complete stranger?

182. Which pet name do you find the cutest (sweetie, honey, babe, etc.)?

183. Do you have trouble accepting compliments?

184. Who is the strongest woman that you personally know?

185. Where do you escape to when you want peace and quiet?

186. Do you believe in miracles? Have you ever experienced one?

187. If you wrote a book, who would you dedicate it to?

188. Which emojis do you use the most?

189. Do you feel comfortable in silence?

190. Does your family have any nicknames for you?

191. What do you think about more than you should?

192. Do you consider yourself a romantic or a skeptic?

193. What is the kindest thing another person has ever done for you?

194. What is your favorite candle scent to fill your home with?

195. What is the most surprising item on your bucket list?

196. Do you believe you have a greater purpose?

197. When was the last time you told someone you loved them?

198. Which day from your childhood do you wish you could relive?

199. How many people would you trust with your life? “Deep questions to ask a Girl”

200. What do you take the most pictures of (food, your pet, yourself, etc.)?

201. What do you consider the most beautiful thing about your personality?

202. What is your spirit animal?

203. Which season do you look forward to all year long?

204. What qualities do all of your closest friends have in common?

205. What song would you love to hear on your wedding day?

206. Which memory do you wish you could erase from your mind?

207. When was the last time you cried inside of a bathroom stall?

208. What have you been putting off for far too long?

209. Which person never fails to put a smile on your face?

210. Which book have you reread again and again?

211. What is the most romantic proposal story you have ever heard?

212. Can you honestly say that you love yourself?

213. Do you have anything you want to ask me?

Deep Questions to Ask a Lady Who Rarely Talks about Herself

Is she an introvert who does not like opening up? You can get her to pour out her heart with these deep questions to ask a lady. 

214. Which astrological sign do you never want to date? Why?

215. Which TV family reminds you the most of your own family?

216. What kind of personalities are you the most uncomfortable around?

217. Are you usually the one who cares more or who cares less?

218. What’s the worst fuckboy experience you have ever personally gone through?

219. What is one thing you hope you accomplish by the end of the year?

220. Who do you think you deserve an apology from?

221. Do you check your Instagram stories to see if someone specific watched them? Who?

222. Since you’ve turned 21, what’s the longest amount of time you have gone without drinking?

223. What music do you listen to when you need background noise?

224. What was the most abnormal thing about your childhood?

225. Has anyone ever given you an actual reason why they broke up with you? What was it?

226. Have you ever dated someone while you were still in love with someone else?

227. Who is your favorite Thought Catalog writer?

228. Are you in any one-sided friendships?

229. Which restaurant do you wish existed in your state?

230. What are the most encouraging words your parents have ever spoken to you?

231. Who is the most famous celebrity you have ever met in person?

232. When you read the newspaper (or a magazine) what is the first section you flip to?

233. How do you think you’ve changed the most since you were in high school?

234. Have you ever bullied someone?

235. Has your favorite color changed since you were a kid? “Deep questions to ask a Girl”

236. Which canceled television series do you wish they would bring back for one more season?

237. Which 90s show do you wish they would reboot on Netflix?

238. What excuse do you most commonly use to get out of plans?

239. Would it be easier for you to give up your phone or your laptop?

240. In your opinion, what is the worst way for someone to propose?

241. What’s the weirdest app you have on your phone?

242. What is one thing you should know how to do by your age, but still can’t figure out?

243. If you could change your first name, what would you change it to?

244. What classic book do you hate?

245. How many friends from childhood do you still keep in touch with?

246. Do you consider yourself a strong person?

247. Do you like movies that make you cry? Or do you avoid them?

248. How many times have you truly hated someone? Who?

249. What is your favorite word in the English language?

250. Do you prefer saying goodbye or ghosting?

251. What is the most bizarre thing you consider a deal-breaker when dating?

252. As a teenager, did you ever get detention? Why?

253. What are your most commonly used emojis?

254. What are some emojis other people use all the time that you have never used once?

255. What’s the closest you have come to marrying someone?

256. How much thought have you put into your future wedding?

257. What phrase did you once use ironically, but has now become a part of your vocabulary?

258. What color pen do you prefer writing in?

259. Not who, but what, do you miss?

260. What is your favorite roller coaster you have ever ridden?

261. Would you want to date someone exactly like you?

262. Has a pickup line ever worked on you?

263. Do you consider yourself an old soul?

Dirty and Deep Questions to Ask a Real Lady

Do you wish to talk dirty? Is she the raw type? You can engage her with these deep questions to ask a lady.

264. What is your favorite thing to do in bed?

265. What is your least favorite thing to do in bed?

266. Where’s the weirdest place you’ve ever had sex?

267. Do you like giving and/or receiving oral sex?

268. Do you own a vibrator?

269. What is your favorite sexual position? What is your least favorite sexual position?

270. Do you like porn?

271. Have you ever been attracted to a woman? If yes – have you ever acted on it?

272. Does the thought of two men having sex turn you on?

273. Have you ever made a sex tape?

274. Have you ever been to a strip club? “Deep questions to ask a Girl”

275. What is the sexiest quality a partner can have?

276. Do you have a fetish?

277. Do you like to be dominated? Or do you prefer to be the dominant one?

278. What are your favorite places to be touched? Where are your least favorite places to be touched?

279. What do you fantasize about?

280. Do you read erotica? What is the sexiest book you’ve ever read?

281. Ideally, how long should sex last?

282. What is the hottest thing a lover can say in bed?

283. Do you like men in uniforms?

284. Have you ever made a booty call?

Deep Questions to Ask a Lady If You Want to Know Her Quirks

289. If you had to switch your career path right now to something totally different – and money was going to be no issue at all – what would you choose to do for a living?

290. If you could find out exactly what your life was going to be like in ten years from now, would you want to know?

291. If Hogwarts was real and your child received a letter, would you let them go?

292. If you were going to live in a nice, average house but one room in the house could be absolutely incredible, modern, and beautiful – which room would you choose? Bedroom, bathroom, family room, kitchen, etc?

293. If you were given the option to give $10 million to charity or to take $5 million for yourself, which option would you choose? “Deep questions to ask a Girl”

294. If you could redo just one decision of your life (so far), which decision would you alter?

295. If you could learn the answer to one of history’s unsolved mysteries, which one would it be?

296. If you had to lose one of your five senses, which one would it be?

297. If you could be an Olympic gold medalist, what sport would you want it to be in?

298. If you could be on the writing staff of any tv show in the world, current or from the past, which show would you want to be a writer for?

299. If you had the option of choosing between a chauffeur, a live-in chef, a personal stylist, a masseuse, and an around-the-clock assistant for the rest of your life – at no cost to you – which option would you go with?

300. If you could go back in time and tell off someone who hurt you, who would it be, and what did they do?

301. If you could get a free one-hour life counseling session from any celebrity or famous person in the world, who would you choose?

302. If you had the opportunity to learn exactly what every person in your life really thinks about you, would you take it?

303. Aside from water, if you could only drink one other beverage for the rest of your life (alcoholic or non-alcoholic), what would it be?

304. If you had to give up one of your limbs in exchange for there being a cure for cancer, would you do it?

305. If you said yes to the question above, would you still do it if no one ever found out that you’re the reason cancer was cured?

306. If you could get a $10,000 raise right now but it would decrease all of your coworkers’ salaries by $1,000 each (and they never knew it was your fault), would you do it?

307. If you could choose any superpower in the world, what would you choose?

308. If you had to cut off all communication with one of your best friends for five years, who would it be?

309. If you had to cut off all communication with one of your close family members for five years, who would it be?

310. If you had to read one celebrity memoir over and over again for the rest of your life, whose book would you pick?

311. If you could accomplish any heroic feat in the world but no one would ever know it was you (solve world hunger, instigate world peace, etc), what would you choose?

312. If someone paid you a million dollars to wear the same exact outfit every day for the rest of your life, would you do it?

313. If you could be a famous athlete, model, comedian, or serious actor, which option would you choose?

314. If you had to settle down in one place for the rest of your life, where would it be?

315. If there was only one insult word you could use against people for the rest of your life, which word would you pick?

316. If you could talk to any type of animal in the world, what would you choose?

317. If you could immediately have your dream body but it would give your best friend twenty extra pounds, would you do it?

318. How would you spend your free time if you could never watch tv, read a book, or spend any of your time on any smart device ever again? “Questions to ask a Girl”

319. If you had to marry a celebrity who was the opposite of the gender you’re normally attracted to, who would you pick?

320. Taking a shower, brushing your teeth, washing your clothes. You can only pick 2 out of the 3 for the rest of your life. Go.

Right from the beginning of things, questions have always been asked. Though, it has always been good questions that got good replies and brought about changes and knowledge.

Accordingly, you should not just ask random questions. You should be able to have deep questions to ask in order to get the answer you desire.

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