150 Engaging Questions to Ask a Friend for Great Conversations

A meaningful conversation requires interesting starters! We have a long compilation of amusing questions to ask a friend that will make your discourse flow joyously.

Aastha Pahadia
Written by Aastha Pahadia , Certified Relationship Coach
Updated on Feb 08, 2024 | 02:59 PM IST | 1.2M
Here are the Funny and Enjoyable Questions to Ask a Friend
Here are the Funny and Enjoyable Questions to Ask a Friend

Do you often wonder how to take a new friendship to the next level? Of course, hangouts are a great way to get to know a person better. And when you plan a get-together, engaging in a meaningful conversation and keeping it going with fun-filled questions to ask a friend can assist you in getting to know the likes, dislikes, and interests of your pals. 

Asking questions is not just about simply getting a response! A list of juicy questions can aid in building deeper conversations by decoding the viewpoints of your mate. Moreover, it also helps in understanding the personality of your friend. Whether you want to spice up an old friendship, bring a tinge of excitement to your slumber party, or challenge your familiarity with your closest buddy- prepping a list of questions beforehand will add a touch of amusement to your companionship. 

So, keep reading for our curated list of interesting questions that call for a fun and interactive sesh with your friends.

From humorous, warm, and personal to witty, explore the list of great questions below to improve your acquaintance with your mate.

Juicy Questions to Ask Your Friends at a Party

Juicy Questions to Ask Your Friends at a Party

  1. Have you ever done any weird things? When, what, and where?
  2. What is the most embarrassing memory you have of yourself? 
  3. Can you describe the most unusual text message you have ever received?
  4. What activity do you enjoy but feel guilty about?
  5. Have you ever tried any weird sexual activity?
  6. Did you ever upload a cringe-worthy post on social media?
  7. What’s the cheesiest thing you have ever done for your ex?
  8. What can woo you instantly? Intelligence or physical appearance?
  9. What is your definition of an ideal weekend?
  10. What’s your life’s biggest regret?
  11. What is your definition of a deal breaker in a romantic relationship?
  12. With whom do you enjoy having meaningful conversations the most?
  13. What is one key tip that you have learned from all your past relationships? 
  14. Is intimacy important for you to be in a relationship?
  15. Fill me in with the numbers of your healthy relationships.
  16. Tell me one of your most awkward moments.
  17. Which activity do you prefer to relieve your stress?
  18. Do you have any odd sexual fantasies?
  19. Are you passionate about anything in your life?
  20. Are you a gossip queen/king? What is the latest gossip you have listened to and passed to others?
  21. What do you prefer more: A big birthday party or a more intimate one? 
  22. How would you define your type?
  23. Did you ever ditch someone?
  24. Have you ever cheated on someone?
  25. What could be a valid reason for someone to cheat on their partner?


Fun Questions to Ask Friends to Know Their Likes/Dislikes

Fun Questions to Ask Friends to Know Their Likes/Dislikes

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26. What do you love about yourself?

27. What is your hobby?

28. Are you into reading? 

29. What kind of music do you prefer to listen to?

30. What’s your favorite season?

31. Do you cook? Share some interesting recipes of yours.

32. Do you have a pet? 

33. Do you play games? Which is your favorite?

34. Which place you would like to go on a vacation and with whom?

35. Do you have any aspirations? 

36. Would you like to communicate via messages or phone calls?

37. Are you a cleanliness freak or despise doing household chores?

38. Which ingredient, snack, or food do you always keep in your refrigerator?

39. Are you a health aficionado or a junk lover?

40. What is your source of inspiration?

41. How do you keep yourself motivated during the low phases of life?

42. Are you a chill-breezy person or do you get super competitive?

43. How do you like to spend your weekend? 

44. What would you pick between partying or binge-watching a series?

45. If you had to choose just one color for your entire wardrobe, which color would you choose?

46. Do you like horror movies or comedies?

47. Which is your most loved snack?

48. What is your favorite family tradition?


Deep And Meaningful Questions to Ask Your Friends

Deep And Meaningful Questions to Ask Your Friends

49. If you were given an entire day to indulge in any activity, what would you choose to do?

50. Are you satisfied with your career graph?

51. What is something that you take pride in regarding yourself?

52. If you want to start your career from the very beginning, would you still choose the same profile or a different one?

53. What is the greatest achievement that you have accomplished in your life so far?

54. What piece of advice would you like to give to your younger sibling?

55. What are some of the things that you are still hoping to achieve in the future?

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56. What is that one skill that makes you stand out as a person?

57. What is something about yourself that you wish more people knew?

58. Which do you tend to focus on more: the past or the future?

59. Is money important for your happiness?

60. Did I ever hurt you?

61. Which is that one thing that can make you lose your temper super fast?

62. Which area of your life are you currently working on to make it better?

63. For you, what is the key ingredient for a long-lasting friendship?

64. Do you see your future with your current partner?

65. What was your first impression of me?

66. Do you hold your anger for long? Or are you a forgive-and-forget type of person?

67. How many times have you experienced the feeling of being in love?

68. Which movie inspired you the most?

69. Do you believe in love at first sight?

70. Do you generally make decisions based on your emotions or your logical thinking?

71. When you receive good or bad news, who is the first person you usually message?

 

Questions to Ask a New Friend

Questions to Ask a New Friend

72. Tell me about your dream house.

73. Do you have any weird fantasies?

74. How do you maintain your health?

75. Are you an emotional person?

76. How do you feel about open-ended questions?

77. What is your preferred icebreaker game?

78. Do you like heels or sneakers? 

79. If you had to ask me a random question, what would it be?

80. On a scale of 1-10, how would you rate your conversation skills?

81. Have you ever tried online dating?

82. What are your opinions about casual flings?

83. Tell me about your fond childhood memories.

84. Which phase of your life so far has been your favorite?

85. What new life experience would you like to gain?

86. If you want to enhance your one skill, what would it be?

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87. What is your comfort food?

88. Do you easily adjust yourself to new surroundings?

89. What is your love language?

90. What is your biggest fear?

91. Have you ever been bullied?

92. Which celebrity or character is your favorite?

93. How do you spend your leisure time?

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

95. If you wish to change your one attribute, what would you pick and why?

96. What has your hardest goodbye in life been so far?

97. What is your tactic to avoid a boring conversation?

98. How do you make a conversation meaningful?

 

Questions to Ask New Guy Friends

Questions to Ask New Guy Friends

99. Who is your celebrity crush?

100. Did you ever have a crush on me?

101. What is that one thing that can turn you on instantly?

102. What are the biggest turn-offs for you?

103. Are you practical or emotional?

104. What do you consider your best physical feature?

105. Is there anything that stresses you out a lot?

106. Do you love watching the sunrise or the sunset?

107. Are you a night owl or an early riser?

108. What are the worst and best decisions you ever made in your life?

109. If you could go on vacation anywhere in the world and money wasn't an issue, where would you go?

110. When was the last time you were jealous and why?

111. Tell me about your career dreams.

112. What is your biggest strength?

113. Are you practical or sentimental?

114. What according to you is unforgivable?

115. How do you resolve disputes and disagreements in your relationship?

116. What advice would you like to give me?

117. What is love for you?

118. If you ever find your partner cheating on you, what would you do?

119. Would you rather be an expert at one thing, or pretty good at many things?

120. What is the one thing you are obsessed with?

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121. What did you dream about last night?

122. What qualities attract you the most toward a girl?

123. Did you ever go on a blind date?

124. What is happiness for you?

125. What are the questions that you tend to ask most often to start a conversation?

 

Personal Questions to Ask Friends

Personal Questions to Ask Friends

126. Are you a spice lover or a dessert person?

127. What are your views on traditions and culture?

128. Do you follow any skincare routine? 

129. What’s the worst nightmare you ever witnessed?

130. Do you feel that you’re young at heart, or an old soul?

131. What is that one quality that can change your emotions towards a person?

132. Who is your role model?

133. If you could live anywhere in the world, where would it be and why?

134. Do you hate any quality in yourself? What and why?

135. Are you a crib-and-cry person or let go of things without even talking about them?

136. What is your philosophy in life?

137. Any life lessons you would like to give to your younger self?

138. Introvert or extrovert — what do you consider yourself?

139. Who is the first person you would dial when you hear a piece of good or bad news? Why?

140. Did you ever drunk dial your ex?

141. Do you accept your partners as they are or try to change them according to your liking?

142. Would you say you are a social media addict?

143. Can you ditch someone because of their physical appearance?

144. Do you believe in astrology?

145. Did you ever protest against something?

146. What exactly do you look for in a partner?

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147. Do you believe in long-term relationships or short-term ones?

148. Have you ever been involved in a one-night stand?

149. What does your dream future look like?

150. How would you like to receive comfort when you are feeling low or upset?

Conclusion

Let your conversations go breezily with our picks of interesting questions to ask a friend. From rejuvenating a chit-chat with an old mate to revealing the personality of your new friend, good questions can do wonders for bonding. Play around with these questions to build a thoughtful conversation to know them better. You can also give a game spin to this questionnaire for a more funny, impactful, and effective discourse.

ALSO READ: 100+ Great Questions to Ask to Get to Know Someone Better

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About The Author
Aastha Pahadia
Aastha Pahadia
Certified Relationship Coach

Aastha is a certified Relationship coach and she strives to help those who seek expert advice on relationships.

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