Deep Questions to Ask a Guy (100+ Questions)


Deep Questions to Ask a Guy: It is the most preliminary thing to know that what kind of person you are living with. But it is still a challenging to gather the things to ask him to know him better as a person. This may sound a bit of serious and extra mature to you but it is really necessary to know a person well before involving in him completely.

Deep Questions to ask a guy

If you are not able to figure out that how to go with it then you need not to worry anymore. I am here to take care of all your problems. Here are some of the amazing deep questions to ask a guy. These questions are not the one of regular kind. But these are something which will really help you to know him better.

100+ Deep Questions to Ask a Guy

1). Can there be any understanding between two people from which one is dumb and other one is deaf?

2). Do you believe in the second chance given by life?

3). Do you think that we should live as if this is the last day of our life?

These types of deep qestions to ask a guy are totally hilarious. You never know what is in his kitty to revert back on this. A guy should be full of life so that he can keep you happy as well. This will let you know that whether he is energetic or just bring lad.

4). Can there be a feeling of love between two arrogant people?

5). Do you believe in demons and angels?

6). Have you ever relied on just the fate and it actually worked out for you?

7). If you know my best friend and she doesn’t know you then would you make a move on her in a night club?

8). Have you ever harassed someone but repented on it later on?

9). If you marry someone with different religion then whose religion would your children follow?

Now this is something which is really serious and deep questions to ask a guy. This can really let you know about his beliefs and acknowledgment towards culture and religions. He should have a broad perspective. And this will clear your doubts that whether he is pure from inside or he is just faking it.

10). Do you find it okay for you to insult someone in front of everyone?

11). What is your idea of correcting someone over certain issues?

12). Have you ever pulled off a prank so bad that it made someone cry?

13). Do you believe that it is because of some incident that you became what you are today?

14). What are the essential qualities that should be there in a person?

15). What is that one thing that you want to change forever in the world’s ritual?

16). Whom would you consider more in an argument, me or your mom?

This is an obvious thing that all boys are mamma’s boy. And there is nothing to be wondered if he takes his mom’s side. But still such deep questions to ask a guy are really fun. You never know when he turns out to be more favorable towards you.

17). Who is that female cousin of yours with whom you share everything?

18). Have you ever got into an ugly fight with your parents?

19). Have you ever abused in front of your parents accidently?

20). If you find someone more perfect than me then would you leave me for her?

21). Do you have any kind of grudges in your heart for someone?

22). Do you feel like going on a holiday and never come back?

23). What is the weirdest fantasy that you have ever created in your mind space?

Now this is something which is like much deserved deep questions to ask a guy. This fantasy can be really weird. And sometimes this can be really adorable too. You cannot guess that what your guy thinks in his leisure time. These questions are just the perfect way to dig into his life.

24). How would you define yourself in just one word?

25). Did you ever think of being a detective?

26). Have you ever spent you whole day doing nothing and still felt so tired?

27). What was that weekend which you would rate 10 out of 10?

28). Which was the most amazing birthday you have celebrated till date?

29). Would you hang out with one of your friend if he is a gay?

Such deep questions to ask a guy is a reality check on their mentality. This is not a crime for a guy to be a gay. And you should know that fact that how he treats everyone. This is really important to know his reviews over the point that how he thinks about all the people.

30). Have you ever felt like that sunset is giving you negative vibes?

31). What do you think is the most important thing for a long term relationship?

32). Where do you rate me in the list of your priorities from 1 to 10?

33). Have you ever felt like being on your own and talk to no one?

34). Do you have heavy debts that you could not pay till date?

35). Do you think that a couple must have a joint account?

36). If moving somewhere else gives me a successful career then would you let me go?

You should always know that whether he loves you this much that he can let you go for your happiness. I know this is totally a hypothetical situation. But still sometimes these deep questions to ask a guy can give you the direction of your relationship.

37). If you could work out without restrictions then how many hours would you spend in the gym?

38). Do you believe in god and his powers on humans?

39). What do you think is the best way to show you affection to someone you really love a lot?

40). Have you ever gone through such situation when you had to see a raunchy advertisement in front of your parents?

41). Do you think that it is necessary to go to the church daily for being religious?

42). Do you find it right to show off when you have lots of money?

43). What is that one thing of your father that you want to adapt?

A guy is always half of what his father is. Such deep questions to ask a guy would let you know his question with his father. There is always that one thing that guys usually copy from their dad. This would be easy for you to know that what that one thing in his case is.

44). Have you ever tried mimicking your mom and get caught?

45). What was the longest duration you had sex for?

46). Do you find it awkward having public display of affection?

47). Have you ever embarrassed someone on a dinner date?

Such deep questions to ask a guy can more sort of like fun. You can revive all his memories of his crazy childhood or of some crazy dinner. These types of questions can lead you to a totally insane conversation with your guy.

48). Did you ever act like drunk when you were actually not?

49). Have you ever excessive amount of drugs forcefully?

50). What are the advantages of being single according to you?

51). What do you think is the most powerful weapon in this world?

52). Have you ever seen someone slut shaming a girl and you remained silent?

53). If you see an accident and you are the only one out there then what would you do?

54). How far would you justify the slut walk by women?

These types of deep questions to ask a guy can prove to be really ice breaker between you two. This is the best way to know his reviews on every single detail of his life). It would make it totally clear that how he thinks about women and feminism.

55). What are the obvious reasons for you to not take drugs in your entire lifetime?

56). Do you feel that there is a song which is totally ridiculous and should not have been composed?

57). Have you ever been hired for a part time job?

58). Have you ever received a friend request from an escort which you accepted?

59). What are the probabilities of you having a threesome?

60). Whom would you consider a morally correct person?

61). Do you think that having a big fat wedding makes it more successful?

62). Are you a shopaholic and that also a brand conscious?

This is just a light question to be asked to a guy. You just get to know his habits more through such deep questions to ask a guy. You can also know that whether his shopping spree landed him to some serious troubles or not.

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63). Would you consider marrying a girl just because of her money?

64). Do you believe in the philosophy that if you betray someone then you get betrayed too?

65). If you are allowed do die on someone else’ behalf then who it would be?

66). What do you think is the true manliness?

67). In the five elements of the body which do you think you belongs the most to?

68). which video game would you choose to live your life like and why?

69). How would you save yourself if you get caught on a crime scene but you didn’t do anything?

Such deep questions to ask a guy are totally crazy. You just don’t know what outcome can turn out to be through such questions. You can get to know that how he handles any difficult situations in his life. This is so unpredictable that when he would have to face such situations.

70). How would you survive if go broke suddenly?

71). If you have to spend your entire life with one animal then which one would you choose?

72). Do you believe in making five year plans for your life?

73). If you have to repay a huge loan then would you sell your home for it?

74). Do you like joint families or nuclear families?

75). What do you think is the best place for a child to grow up at?

76). Would you accept being immortal although your partner is not being immortal?

Such kind of deep questions to ask a guy reveals a lot about a man’s personality. This would let you know that whether he is a self centered person or he really values love and sacrifice in his life. These little things really matters a lot in a relationship.

77). If you were a vampire then would you date any human?

78). What do you think eternity is?

79). Do you believe that there is hell and heaven right here on earth?

80). Do you think that aliens exist?

81). How would you repay the debt of saving your life to someone?

82). Among your entire family if there is only one whom you can save from dying then who it would be?

83). Would you involve in the cut throat competition to achieve success?

In this modern world everyone possesses the feeling of revenge and competitiveness. Such deep questions to ask a guy is just measure to know that how far he can go to achieve success in his life.

84). Would you call off your marriage if you suddenly realize that you do not love your partner anymore?

85). What do you think that one thing which can replace millions of dollars in your life?

86). How would you manage to convince someone unknown to you to give his money to you?

87). Have you ever seen someone dying in front you and you could not do anything?

88). Have you ever fantasized about someone this much that you ever forgot to eat?

89). What excuse would you make if you do not want to go on a date with some girl?

Such deep questions to ask a guy can be very useful for you for the near future. Whenever he will make an excuse to drop the idea of hanging around then you will come to know it easily.

90). Have you ever seen a two faced person?

91). Did you ever tried something and then thought why did you ever try it?

92). How sinful do you think that sex outside marriage is?

93). Have you ever been the victim of racism?

94). Have you ever felt like working for an NGO?

95). What is that one thing that keeps you happy even in the odd times?

Such deep questions to ask a guy are the quite light things. You should know that what makes him happy and what not. So in the hard times you can keep him cheer up always). This is important for you to keep him happy go lucky always.

96). Do you sometimes find yourself totally self obsessed?

97). Do you think that selfie addiction is a type of abnormal mental condition?

98). Have you ever generated hatred towards a person so much that you visualized yourself killing them in dreams?

99). Do you think that everyone has a muse in their life?

100). Do you think that being adventurous makes you coolest among all?

101). What is the true meaning of life for you?

102). If given a chance would you kill someone you do not like at all?

These types of questions can tell you a lot of things about your guy. Such deep questions to ask a guy are a must for you . You can know that whether there is someone in his life whom he hates a lot or not.

103). Did you ever felt like petting a wild animal in your home?

104). Do you feel that your life could have been much better without cell phones?

105). What was the worst outcome you faced because of lying?

106). Have you ever felt god’s presence around you in your tough times?

107). Have you ever been admitted to a rehab centre in your life?

Such deep questions to ask a guy are a spot light on his past. It can also be possible that he does not want to talk about it anymore to anyone.

108). Do you think that juvenile culprits should also be treated the same as the adult ones?

109). Have you ever been abused physically?

110). If you could swap a thing or two from a different profession then what it would be?

111). If given a chance would you even die for your country?

112). If you are fuming over someone in public then what is that thing which holds you back from hitting him?

113). What do you want to do so that people can remember you after you die?

114). If you could make travelling free to a specific place then which it would be?

115). If you have to elope with someone on an islan then whom would you take along and why?

Now such are interesting as well as deep questions to ask a guy. You should know that whether there is someone else in his life or not.

116.if you could bring something from god’s place then what it would be?

117). Which song motivates you a lot?

118). Which would you consider the most thrilling job in the whole world?

119). If you could implement a law then what it would be?

120). What is your favorite one liner to try on girls?

121). Have you ever managed to make headlines in the newspaper for something good?

Such deep questions to ask a guy are really interesting ones. This can be out of something bad as well.

122). If you could master something from music or art then what it would be and why?

123). Which would you call a perfect day? complete a dare which language would you choose to sing a song in?

125). Why do you want to travel the time?

126). Have you ever tested your friend’s friendship and does he even know about it?

Such deep questions to ask a guy can bring back his bitter memories too. So take care while asking such questions.

127). What time of your life you want to relive again?

128). Which is that one memory of your past you wish never happen to you again?

129). If you had to change your name then which one would be the new?

130). If you could be part of an event from history then which one it would be?

131). Which is that one photo from your childhood that you do not show to anyone?

132). What inspires you to earn more and more money?

There should not be any negativity connected to it. I mean there should not be something evil that inspires him for this. Such deep questions to ask a guy are really important.

133). If you could live like one Disney characters then who would you pick?

134). What do you want to be the last words from you?

135). Would you share your accounts password to someone while dying?

136). What is that one thing that you managed to not change since your childhood?

137). What was that dream of yours that turned out in reality?

138). Do you think that spending too much of money on your wedding is correct?

Such deep questions to ask a guy are just an idea to know his mind set about it.

139). Will you marry the girl you do not like just to complete your mother’s last wish?

140). What is your craziest fantasy about nature?


These awesome deep questions to ask a guy are really wonderful. I hope you have gone through all of them now. And I really look forward to the fact that now you would not be having any difficulties to lead the conversation.

These deep questions to ask a guy are simple and do not contain any hidden meaning. It is always good to keep the things simple between you and him. The great straight forward you will be, the more things will lead to an easy going direction.

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Nagama Ansari is a well-known blogger and digital marketer, working in the industry from several year, and has written more than 1000+ well-researched information guides and product testing review articles..