Questions to Ask Your Best Friend


In this post, I have listed out some interesting questions to ask your best friend. No matter for how long you guys are besties, but digging more is never too bad. It is your turn to take some initiative and take the friendship between you to a next level.

Let’s get started.

Questions to Ask Your Best FriendQuestions to Ask Your Best Friend

1). What was the name of the person you had a crush on in school?

2). Have you ever liked the same person as I did but never told me about it?

3). Did you ever double cross me in school or college?

4). What are the things you are regretful for doing in your life?

5). What are the things you are regretful for not doing in your life?

Its ok, if you do not know about the past of your bestie, you can still know it through the questions to ask your best friend. You should know that what they always wanted to do but could not and they are still regretful about it.

6). Which parent do you resemble the most?

7). Who do you find closer to among both your parents?

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

9). Can you hula hoop for 10 times in a row?

10). Which ice-cream flavor is your favorite one?

11). Where do you often eat out when alone?

12). What do you like to cook on weekends?

13). What embarrasses you the most about yourself in public?

14). Have you ever thought about entering politics?

15). What are the things you are most passionate about?

16). What are the things that you keep as a secret from everyone but can share with me?

17). What do you often like to talk about?

18). Where do you wish to live one day?

19). Which country’s citizenship you want to have?

20). Who do you feel really envy with?

You should know that who that person they are really jealous or envy of is? Questions to ask your best friend are a great way to let them get over with their hard feelings about someone.

21). Who do you think is the person around you who is really blessed?

22). What are the things you really struggled for?

23). If you are not able to have children of your own then would you ever adopt one?

24). What would you do if you find out that your parents are not your real parents?

25). What is the thing you are embarrassed of committing but you really enjoyed it?

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26). How far do you think you are materialistic?

27). Do you have any kind of obsessive possession about something?

28). Did any of your partner had an obsession about you?

29). How many relationships you have been into?

30). What was the last time you cried like hell and why?

31). If you were a pastry then which flavor it would be?

32). What would you pick among ice-cream and chocolate?

33). Have you ever baby sit a child of your relative?

34). Have you ever done something as a freelance work to earn some extra money?

35). What is the most important piece of thing in your bedroom that you cannot live without?

36). Which is that memory that you cherish a lot?

37). What was the age of your mother when you born?

38). At what age you first learnt to ride a bicycle?

39). Did you ever fail in any grade in school?

40). Do you repent about some incidents you were sorry for but could not say it?

41). What would you like me to do to make you feel happier?

42). If you had to pick a sport for us to try out together then which one it would be?

43). Which is that celebrity you want to befriend?

44). Have you ever envied me all in your heart?

45). What would you pick among 3 kittens and 3 dogs?

46). If you had to give me the right of making one important decision of your life then which it would be?

47). Are you happy with the current phase of your life?

48). What are the things that you are not happy about right now?

49). Have you ever suffered a fracture?

50). What were the things you were good at in school?

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51). Did you ever won any medal or award for anything in school or college?

52). Who is that celebrity you have a huge crush on?

53). If you could buy something and money was not the issue then what would you buy?

54). Which are your favorite flowers?

55). What piece of art would you like to have in your room?

56). Which is that piece of food you would not like to eat at all at any cost?

57). How would you like someone to comfort you when you having a bad time in your life?

58). Have you ever suffered a life changing incident in your life?

59). Did you ever get life threatening calls from someone?

60). What kind of partner do you want to spend the rest of your life with?

61). Do you believe in aliens?

62). Which do you think the most beautiful place on earth is?

63). Who is that relative of yours you would never want to visit in your entire life?

64). Do you believe in ghosts or god?

65). Have you ever encountered something which was hard to believe but was 100% real?

66). Do you eat expired items sometimes?

67). What is the yummiest item right now in your fridge?

68). Where do you like to spend your holidays?

69). What is your shoe size?

70). What song instantly turns your mood off?

71). What are the things that can cheer you up instantly?

72). What do you keep under your bed?

73). Which is your favorite pizza chain?

74). Which is that song you are never tired of listening?

75). Have you ever pulled off a prank on someone and succeeded too?

It is always interesting to listen to the things which makes both of you smile. Questions to ask your best friend is a way through which you can explore the unheard things of each other’s life.

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76). What was the last time when someone bluffed you?

77). Do you make any plans for future?

78). Where do you like to spend you alone time?

79). What do you to reduce your anger?

80). Do you feel like there is someone else in your room and you can feel it but cannot see it?

81). Who are the top three celebrities according to you?

82). Who do you think is the really overrated actor or actress?

83). What did you ever aspired to be as a kid and do you think you are anywhere near to it now?

84). Who do you think should be the ruling party right now?

85). What was the best book that you ever read in the recent times?

86). Which is that one activity you would like to recommend me to do on a daily basis?

87). What makes you feel really weak?

88). Where you inner strength lies?

89). What are the situations that makes you feel miserable?

90). Who is your favorite author in the recent times?

91). What is the adverse effect of being modern according to you?

92). What is your least favorite childhood memory of all time?

93). Which is your favorite pet animal and why?

94). Which is that company you want to work for at least once in your lifetime?

95). If you get the presidential powers for a day then what would you do out of it?

96). Which is that theory you really believe in?

97). If sky is the limit then name the profession you want to practice once?

98). If could own a piece of land then where it would be?

99). What would you name the home you bought?

100). Do you like someone?

101). Why do you think getting married is important?

102). Who is that person in your life who has influenced you a lot?

103). Who is that celebrity whose interviews you like to watch a lot?

104). Which are your favorite lines from any song?

105). What do you like more, fit clothes or loose ones?

106). On the first day of your job, how would you try to befriend everyone?

These are some of the open ended kind of questions to ask your best friend. This is like getting to know them but in a totally different way that you never try to discover before.

107). If you get all the powers to rule the world for a day then how would you handle it?

108). If you ever going to open up a business then what would you name it?

109). What is the weirdest thing you have ever done on a date?

110). What are the things you want to achieve by the time you get retired from your job?

111). If you look back in the last year, what are the things that made you smile so far?

112). Who is your favorite sleep over buddy?

113). What would you choose between a bottle of wine and a bottle of champagne?

114). Which is your favorite flavor of a candy bar?

115). Which is that place that you want to visit once?

116). Which is that illegal work that you want to do at least once no matter what its results are going to be?

117). What is your idea of being so energetic all the time?

118). If you are to buy a new house then where would you like to buy it?

119). Between a cute kitty and a wise own what would you choose?

120). Which is your all-time favorite cartoon movie?

121). What do you love the most about the life that you are leading right now?

122). What do you find so awkward that people do publically?

123). Have you ever been to a rave party?

124). Do you have any police case running on you right now or ever in the past?

125). If you had to get a new tattoo then what it would be all about and where would you like to get ink it on your body?

This is one of the most thoughtful kind of questions to ask your best friend. Tattoos are like the representation of your thoughts and the choice of their tattoo represent what is running in their mind.

126). How much do you want to save for yourself until you get retired?

127). Which is the most romantic things that you have ever done for someone?

128). What would you like to rate me on a scale of 1 to 10.

129). What is the most critical situation that you have ever handled in your life?

130). Would you ever come back if you get a job out of the country?

131). Can you kiss someone just for the sake of a bet or money?

132). What you do not like about your life?

133). What are the things that you want to change about your parents?

134). If you could change your surname and keep whatever you wanted to then what would you do about it?

135). Have you ever thought about moving out of your parents’ home?

136). If money was not an issue then what kind of job you would be doing right now?

137). Which is the most bizarre incident that has ever happened with you?

138). Why do you want to get married and get settled with someone?

139). What would you go for, love marriage or arranged marriage?

140). If there could be a place where you could spend time when upset then what it would be like?

Hand Picked Stuff for You:


This section has all the flavors of your friendship combined together. These questions to ask your best friend are crazy, open ended, funny, some intense and mostly all are answerable. There is nothing like objectionable that I have listed out in this section.

I hope you guys have good time knowing each other more and more. And it will only end up strengthening the bond of your friendship like never before. So, go ahead and break the barriers and seal your friendship for a lifetime. Because friends are the only one who would keep up with all your tantrums even for a lifetime.

Keep vising to get new questions to ask your best friend.

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Nagama Ansari
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..