139 Deep Questions To Ask A Guy

by Updated on July 23, 2019

Trust us, when it comes to asking a man questions, it’s easy to guess how important the questions are to him, from the way he thinks them through. If he answers immediately he hears them, he’s a joker, and shouldn’t be taken seriously. But if he ponders on them briefly, supports his answers with additional statements, and still has room to say more, then that’s a guy who means business.

This may not apply in all cases, though. Search his mind, test his intellectual prowess and his commitment to you with the questions below:

Deep Questions To Ask A Guy

1: In the next 10 years, where will I find you?

2: Apart from the field of expertise you’re already in, which other work can you do successfully?

3: Have you had reasons to doubt your creative ability?

4: What drives you toward becoming successful?

5: Who is the first person that hears about your day at work?

6: Where would you want to spend the rest of your elderly life?

7: What influenced your style of dressing?

8: Do you think you would have lived better if you weren’t raised by your parents?

9: What influenced your choice of music?

10: Who is your most revered intellectual icon?

11: If you become the president of your country, what will you change or introduce in your first tenure in office?

12: How well do you deal with disappointments?

13: Have you ever had any reason to betray anyone?

14: Can you count your career breakthroughs so far?

15: Where would you rather not visit in the world if you were given access to travel?

16: How do you assess strangers: by their dressing or manners?

17: Which one event changed your mind about humanity?

18: How do you figure out what to do when on a crossroad?

19: Have you been in an abusive relationship?

20: What’s your take on domestic abuse?

21: How do you handle unbearable people?

22: Under what circumstance would you choose peace over conflict?

23: Have you ever considered skydiving?

24: How often do you drink water in a day?

25: What is your style preference when it comes to wristwatches?

26: How well have you grown after college?

27: If you meet a psychopath now, would you be able to identify him?

28: What crucial ways will you train your children?

29: Has any life experience taught you an unforgettable lesson?

30: In your choice of a life partner, what three factors make the topmost list of your priority?

31: Which decision have you made that you wished was never taken?

32: In politics, do you think that the masses are ably represented by the ones they elected?

33: Which invention do you term the most revolutionary in the history of mankind?

34: What did you give up on, that you regretted not waiting a bit patiently for the end?

35: What is the landmark achievement that you attained, which helped you climb higher in your career ladder?

36: What time of the day are you most productive?

37: Which is better, efficiency or effectiveness?

38: Which invention on earth do you consider very unnecessary?

39: Can you forfeit wealth for knowledge?

40: Are you conversant with astrology?

Deep Questions To Ask Your Boyfriend

Deep Questions To Ask Your Boyfriend

41: Do you believe we have a future together?

42: Have you had any cause to doubt our love?

43: Do you trust me?

44: Which challenge do you avoid having in your life?

45: What’s your biggest fear about us?

46: Can you give up your job for a move with me?

47: How much do you esteem my family members?

48: What can you let go of me for?

49: Do you think our relationship is progressing healthily?

50: Will you cherish becoming a single father?

51: What are your thoughts on extramarital relationships?

52: Tell me, do you honor me more than your dreams and aspirations?

53: What is your favorite activity with me?

54: Which food won’t you mind eating on a daily basis?

55: What will you do if I cheat on you?

56: How will you react if I exhibit any sign of jealousy when I see you with a lady?

57: Between both of us, who is the most tolerant?

58: How much do you believe that I love you?

59: What’s your most recent pet peeve?

60: When will you move from your parents’ house?

61: What’s the most appropriate time to start a family?

62: Will you be okay if I got a job outside our present location?

63: Do you think the distance between us will affect our relationship?

64: Am I your only girlfriend or one amongst many?

65: How much do you value education?

66: What offence will trigger you to beat me?

67: Were you abused as a child?

68: Will you like to be the kind of father your dad was, to your children?

69: What’s that one dream you can never give up for anything?

70: If asked to choose between us and your parents’ wish, which one will you hold onto?

71: What’s your relationship with your mom like?

72: How well do you know your friends?

73: What new thing did you learn last week?

74: Will you want a marriage based on love or one based on trust?

75: What, in your opinion, needs to change in our relationship?

76: Do you think I’m getting along well with your sisters?

77: What has changed in you ever since you met me?

78: Do you think I can disappoint you?

79: What has been your biggest achievement in life?

80: Will you ever want us to move in together before marriage?

81: If we break up today, will you miss me?

82: Can you tell me where I go wrong if I do?

83: Asides loving me, what else do you have for me?

84: Will you want me to have nothing to do with other men, given the opportunity?

85: Which of my friends do you feel more comfortable talking with?

86: What do you think can strengthen communication between us?

87: Which childhood fear of yours happened?

88: What’s your love language?

89: Are you proud of me?

90: What has our relationship denied you of?

91: Where will you want us to live if things eventually works out between us?

92: Is there any secret you’re keeping that you think I should know?

Questions To Ask Your Crush

Questions To Ask Your Crush

93: What is your biggest dream in life?

94: How well do you get along with your sisters?

95: What are you the happiest about?

96: Will you ever fall in love with me?

97: Do you like my company?

98: Have you found the one you love?

99: What was your past relationship like?

100: Are you a work kind of person or a fun kind of person?

101: Are you in love with me or the idea of us together?

102: Does love scare you?

103: What do you want from life that you’re yet to have?

104: Have you ever been burned by love in the past?

105: Who is the most loving person in your life?

106: Do you have an ex?

107: Have you ever been in love?

108: Is there any hope of a relationship between us?

109: What is the singular reason why you will give up on love?

110: Do you esteem a relationship exclusive of others?

111: Are you a playboy?

112: Will we ever go out on a date?

113: When will we have a second date?

114: Do you think that I am your kind of girl?

115: After schooling, what’s next for you?

116: What attracted you to me?

117: Will you like to start a relationship with me?

118: Have you ever considered asking me out?

119: How much passion do you have for me?

120: What’s your thought on sex before marriage?

121: Do you think we can bond well as friends?

122: What do you get most excited about us?

123: If we start a relationship, what will be different from what you’ve had before?

124: Will you like us to just be friends?

125: Do you have female friends?

126: Am I smarter than you are?

127: What makes you want to talk with me?

128: Do you love partying?

129: Will you be happy if we started a relationship?

130: What’s your favorite restaurant?

131: Who do I remind you of?

132: If we don’t become a couple, will you get jealous if you see me with another man?

133: What’s your thought about our friendship?

134: Did you ever think we would start talking to each other?

135: How confident are you?

136: What line of career are you pursuing?

137: Do you believe in God?

138: What activity do you engage in during your leisure?

139: How do you handle loneliness?

Also Read: 137 Flirty Questions To Ask A Girl

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