Even the most seasoned social butterflies struggle to articulate a good conversation starter at times. When you are at a business meeting, a party, or simply spending time with friends or family, coming up with an interesting conversation starter can be incredibly difficult. 

Chances are you don’t want to use mundane topics and begin a conversation upon boring small talk. It’s time you put the questions surrounding the weather and what they did the previous weekend to rest. No one wants to really answer those types of questions. Nor are they very insightful or entertaining.

Yet, you need to consider the fact that not every conversation starter is appropriate for every setting. You won’t say the same thing on a date that you would while talking to children or your family. Ultimately, conversation starters can only truly be effective if used in the right context and setting. 

When considering the 101 conversation starters listed in this article, remember that they are meant to break the ice. They are not meant to get someone to like or adore you immediately, but they will likely pique their interest and make them want to learn more about you. So without further ado, let’s dive in and look at 101 of the best conversation starters that you can use in a multitude of different situations.

The 101 Best Conversation Starters

1. Would you consider yourself a spiritual person, and if so, what do you think it means to be spiritual? 
2. What has been the most challenging thing you have ever had to go through in your lifetime?
3. Are you a fan of podcasts, and if so, what is your favorite one that you like to listen to?
4. In the last year, have you been to any exotic or interesting locations? 
5. What would you say is something that someone is always shocked to learn about you?
6. Are you happy and content in your current job, or do you see yourself doing something else with your life in the near future?
7. If you had the ability to solve one significant world issue, which one do you think you would choose?
8. If you found out that your life was ending tomorrow, what would you choose to do with your last day today?
9. What life lesson do you think took you too long to figure out?
10. During your lifetime, what is the best advice you have been given? 
11. Are you someone who can’t live without technology, or would you be comfortable living off-grid in a cabin in the woods? 
12. Do you believe karma is real and if so, why? 
13. Before you make a telephone call, do you prepare what you are going to say?
14. Out of everything in the world, what is the one thing you can’t see yourself living without?
15. Do you believe climate change is a natural phenomenon, or do you believe it is one of the biggest lies of current times?
16. How many countries have you explored since you began traveling, and where do you plan on traveling to next?
17. What movie or TV series can you repeatedly rewatch no matter how old it becomes?
18. If you could banish one thing from your life, what would it be?
19. Would you say that you find it easy to open up to people, or are you a guarded person? 
20. Are you an exuberant social butterfly or more of an introverted soul?
21. If you could converse with any famous person who has passed away, who would it be?
22. Is there a particular talent that you wish you had?
23. Is there a charity that you want to volunteer at, and if so, why?
24. What action have you managed to achieve in life so far that you never believed possible years ago?
25. Do you want to own a home in the future, and if so, can you explain what your dream home looks like?
26. If you were gifted the chance to start your own company tomorrow, what type of business would you open?
27. In 10 years, where do you see yourself living?
28. Could you share with me one of your most cherished memories?
29. Do you think there is a purpose for humankind in this world?
30. Which people, past or present, have made you into the person you are today?
31. Do you stick to your opinions and conclusions even if you have been proven wrong?
32. Is there a certain quality that you possess that you want to nurture more, and if so, what is it?
33. If you were gifted the chance to visit any place in the world right this moment, where would you choose to visit?
34. Who is your favorite musician and why? 
35. What is something expensive that you indulge in that you deem worth it?
36. Do you believe chivalry still has a place in modern society?
37. Are you a team player or someone who works better alone?
38. What would you say has caused you the most hurt in life?
39. If you were lost in the Amazon jungle or desert, which two people would you want with you?
40. Do you find it unchallenging to make friends at social gatherings?
41. Can you tell me the one thing you fear most in this life?
42. Do you feel love is a natural phenomenon or simply a chemical reaction meant to ensure the procreation of the human race?
43. If you found out you were a millionaire when you woke up tomorrow, what would be the first thing you would purchase or do?
44. What in your life are you most grateful for?
45. What do you think the best personality traits are that a person can have?
46. Are you a loving person, and if so, what do you deem to be your love language?
47. Do you think human society can exist without laws or rules?
48. What is the most dangerous activity you have ever participated in?
49. What do you think the future you will remember about your current self?
50. Do you believe in twin flames or soul mates?
51. What is the strangest conspiracy theory that you believe?
52. Are you a person who can remain friends with your ex?
53. Are you someone who can love more than one person at the same time?
54. What would you deem to be the most interesting thing about yourself?
55. If you weren’t here talking to me, what would you be doing?
56. Can you tell me five fun facts about yourself?
57. Who is the person you look up to the most?
58. Do you have an extensive bucket list, and if so, what are the top three items on it?
59. Do you think opposites attract, or do you believe like-minded people are more compatible in romantic relationships?
60. Do you think love is a personal choice or a feeling?
61. Do you believe in the supernatural and extraterrestrial life?
62. How well do you think you would be able to survive a global disaster that wholly changed the way the world is now?
63. Do you see yourself having a few children in the future, and if not, why?
64. Would you be willing to date or marry someone who has different political views from you?
65. Do you think jealousy is a healthy trait in a relationship, or do you believe it’s one of the most toxic?
66. Is it better to have a broad knowledge of many topics or a deep knowledge of a select few?
67. Do you believe in unconditional love?
68. Can you tell me what the most controversial opinion you have is?
69. What about the future scares you the most?
70. Do you believe there should be certain limitations on free speech?
71. Is there a particular invention you would uninvent if you had the chance, and what is it?
72. If you were a social media influencer, what would you be famous for?
73. In your opinion, what does the perfect marriage look like?
74. If you could choose to be on a reality television show, which one would you prefer to be on?
75. Would you grab the opportunity to take your boss’s job if it was offered to you?
76. If you had no commitments, what would you want to do every day?
77. Are you someone who prefers to spend money or save money?
78. Is there anything you would change about yourself if you had the opportunity to do so?
79. What age would you want to stay if you were granted immortality?
80. Where do you find the most enjoyment in the world?
81. If you suddenly became a trillionaire, would you still choose to work every day?
82. When you think about getting older, what are you looking forward to the most?
83. What activities do you love to do in your free time?
84. Who is the most important person in your life currently?
85. Are you someone who believes that social media is destroying people’s social communication skills?
86. Is there anything that you have failed at recently?
87. What inspired you to choose your current profession.
88. Which movie do you think earns the title of being the “funniest ever made?”
89. What is something you think is popular right now that won’t be in five years?
90. If you could create one new law that everyone in the world had to obey, what would it be?
91. Are you close to your family?
92. Can you tell me the worst trend that you have taken part in?
93. What event has ultimately changed how you view something, and what view did it change?
94. Do you feel it is ever okay to tell a lie?
95. Are you dealing with any childhood traumas that you think I should know?
96. In life, what are you the most afraid of losing?
97. Are you a person who loves to live in the moment, or do you prefer to plan every detail of your future?
98. What is the most absurd social media trend you have witnessed lately?
99. When you think of love, who or what comes to mind immediately? 
100. Do you think it’s wise to fail at something for the sake of trying, or do you believe that something should not be attempted if it’s likely you will fail? 
101. Do you believe our choices matter in the grand scheme of things? 

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