145 Fun Questions To Ask Your Best Friends

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best friends laughing together
Self

Your best friend is your partner in crime. She’s the one you know will be the Thelma to your Louise, and the Butch Cassidy to your Sundance Kid. She’s your confidante, your ride-or-die, and the one who acts as an absorbent shoulder when that one guy breaks your heart.

You love her to pieces and are a good friend to her, but even if you’ve known her for years, you might not know everything about her.

The more you know about your best friend, the more you will love her. It helps you and can make a huge difference in the way you see one another. That’s just the way friendship goes!

Even if you’ve been friends since grade school, these conversation starters will give you something to talk about. And I’m willing to bet that these questions to ask your best friend will help you go deeper in your friendship.

RELATED: 150 Inspiring Friendship Quotes To Show Your Best Friends How Much You Love Them

Plus, even if you’re just getting to know someone other than your close friends, it will make your heart rest easier knowing you’ve put in effort to form a connection.

145 Questions To Ask Your Friends

Fun Questions to Ask Friends

1. What was the greatest prank you’ve played on someone?

2. What was your most embarrassing memory?

3. If you could live anyone’s life for a week, who would it be?

4. You just found out that you’re a distant relative to royalty, and you now have a royal title. What 5. title would you want, and what country would you want to represent?

6. Which TV show would you star in?

7. If you could travel to one of the planets, which planet would you go to?

8. What would you like to be known for?

9. What would you name your next pet?

10. Who is your hero and why?

11. What is one thing you’d like to cross off your bucket list?

12. If there was a zombie apocalypse tomorrow, what is the first thing you would do?

13. What is your most treasured possession?

14. If you had to be reborn again, who or what will you choose to be?

15. If you could have a magical power, what power would you choose?

16. Where is the worst smelling place you’ve been?

17. When was the moment in your life you laughed the hardest?

18. What would be your perfect day? Plan it out from waking up to bedtime.

19. What do you do when no one else is around?

20. If you had three wishes, what would you wish for?

21. You just won $10,000, what would you do with the money?

22. What is the luckiest thing that's ever happened to you?

23. If you had to create an alter ego for yourself, who would it be and what would you name them?

24. If you had to describe yourself in only three words, what would you choose?

25. If you could time travel, where would you go?

Deep Questions to Ask Your Best Friends

26. What are you most afraid of?

27. What do you think is your biggest accomplishment today?

28. If you could have a “life redo,” what would you do differently knowing what you do now?

29. How do you comfort yourself after a terrible, horrible, no good, very bad day?

30. Do you believe in reincarnation? Why or why not?

31. Which friend of yours impresses you the most? You’re not allowed to say me.

32. Which family member do you feel closest to?

33. Do you have any recurring dreams?

34. If past lives exist, what do you think your past life was?

34. What emotion do you feel you experience the most?

36. So far this year, what do you think was your best moment?

37. Were there any careers that you almost pursued, only to change your mind at the last minute or just have it not pan out? What happened? Do you regret it?

38. If you could do anything for the rest of your life, what would it be and why?

39. What is your biggest fear?

40. Where do you hope to be five years from now? Ten? Fifteen?

41. If money was no object, what would you buy?

42. When have you felt the most proud?

43. When have you felt the most challenged?

44. What would you change about your life if you could?

45. Do you have any phobias?

46. Who do you look up to the most, and what qualities do you love about that person?

47. Do you want to have kids one day? How many?

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

RELATED: 55 Epic Songs About Friendship To Share With Your Best Friends

Random Questions to Ask Friends

49. Did you ever experience something paranormal? If so, what did you see?

50. If you could have dinner with any famous historical figure, who would it be and why?

51. If you could be an animal, what would you be?

52. If you could have the perfect day, what would it look like?

53. What is your least favorite food and why?

54. If you could hang out with any celebrity, dead or alive, on a regular basis, who would it be?

55. What do you think life will be like when we’re 85?

56. What superpower would you want to have?

57. What is your favorite flavor of ice cream?

58. Let’s say you lived in a fantasy world. What mythical being do you think you’d be born as?

59. Which cartoon characters did you love as a kid? Which ones did you hate, and why?

60. If you could pick an age to stop aging at, what age would you want to stay? Why?

61. Do you believe in aliens?

62. What did you dream about last night?

63. What is your favorite thing you own and why?

64. Which celebrity would you want as your other BFF and why?

65. If you could travel anywhere in the world, where would you go?

66. If you had to eat one expired item in your fridge, what would it be?

67. If you could make one wish right this second, what would it be?

68. Do you believe in ghosts?

Questions to Ask New Friends

69. What is your all-time favorite song?

70. What was your favorite memory that you had at school?

71. Who is your favorite reality TV star?

72. Do you have a go-to dinner recipe you swear by when you want something tasty but impressive? What is it?

73. What are the first three laws you’d try to pass if you became president?

74. What is your opinion on couples’ costumes or costume parties? Do you think it’s overkill or adorable?

75. What time period would you live in, if you could live in any time?

76. What is a skill you’ve always wished you had, but never quite managed to get a hang of?

77. Is there a cartoon character you can really relate to? Who is it, and why?

78. Out of all your family members, who are you closest to?

79. What is your favorite quote?

80. What did you want to be when you grew up?

81. What food will you absolutely never eat and why?

82. What one cause are you passionate about?

83. If you were an animal, what would you be?

84. Do you believe in soulmates?

85. Do you like roller coasters?

86. If you could only listen to one singer or band for the rest of your life, who would you choose?

87. What is your favorite holiday and why?

88. What is one thing most people don’t know about you?

89. What book has impacted you the most?

90. If you were going to get some ink, what would you choose and why?

91. What would your dream vacation consist of?

92. What is your absolute dream job?

93. What are your top three biggest pet peeves?

94. Who was your very first crush?

95. What foreign language(s) would you want to master and why?

Awkward Questions to Ask Your Friends

96. What would you do if your significant other didn’t want to work anymore, and expected you to support them?

97. When was the last time you cried?

98. What is the most childish thing you still do?

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99. What is the dirtiest thought you’ve ever had?

100. What is the most disgusting thing you’ve ever done?

101. What is the most disturbing fantasy or dream you’ve ever had?

102. What is the most awkward experience you’ve had with a crush?

103. What is the meanest thing you’ve ever said to someone?

104. What is the cruelest thing you’ve ever done to someone?

105. How many people can someone sleep with before you secretly judge them for their “number”?

106. What is the first thing you’d do if you woke up one day and you were the opposite sex?

107. What is the biggest romantic fail you’ve ever experienced?

108. What is the weirdest thing you’ve done when you were alone?

109. When is the last time you were flat-out rejected and how did you handle it?

110. What is the most embarrassing thing your parents have caught you doing?

RELATED: 50 Friendship Quotes To Share With Your Best Friend, Human Diary And Other Half

Questions to Ask Your Friends About Yourself

111. What did you first think when we met? Did you think we’d be friends this long?

112. Is there a smell that reminds you of me?

113. If we met earlier, do you think we’d still want to be friends? Or, do you think we’d be way too different?

114. Do you have any advice for me that you’ve been wanting to tell me, but haven’t gotten around to saying it quite yet?

115. What am I most afraid of?

116. What has been my greatest accomplishment?

117. When did we meet?

118. Who was my biggest crush when we were younger?

119. Why do you think we get along so well?

120. What do you do that makes me laugh the hardest?

121. What drives me crazy?

122. Which two fictional BFFs are most like us?

123. When were you most impressed by me?

124. What are the best and worst dates I’ve ever gone on?

125. What is the first thing I would do if I won the lottery?

Juicy Questions to Ask Your Friends

126. Who was the worst boyfriend you ever had, in your opinion?

127. Did you ever send someone a gift that they clearly hated? What happened?

128. Did you ever drop acid or have a hallucinogenic trip? What was it like?

129. What is a little-known skill you have?

130. Has anyone ever mistaken you for someone else, only to do something they regretted because of it?

131. What is the one thing you’d do in bed with someone if you had no inhibitions whatsoever?

132. What is the biggest mistake you’ve ever made in bed?

133. What is the weirdest thing you’ve ever done in front of other peopler?

134. What is the biggest dating disappointment you’ve experienced so far?

135. How far would you go to land the guy or girl of your dreams?

136. What is the biggest lie you’ve ever told without getting caught?

137. What is the one aspect of a guy’s personality that is either an immediate turn-on, or turn-off?

138. What would be on the gag reel of your life?

139. What ridiculous thing has someone tricked you into doing or believing?

140. Do you have any regrets? If so, what are they?

141. What is the craziest thing you’ve ever done to attract a crush?

142. What do you like most and least about your own appearance?

143. If you could erase one past experience, what would it be?

144. What is your favorite go-to move for getting attention from the opposite sex?

145. What is the last lie you told?

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Ossiana Tepfenhart is a writer based out of Red Bank, New Jersey. She writes primarily about lifestyle, food, finance, and relationships. You can follow her on Twitter.