Last Updated on March 15, 2025 by Team CrazyJackz
Now tell me honestly..
How many times did you want to start a conversation with someone new and couldn’t know what to talk about..? How many times did you plan to chat with your loved ones, but couldn’t potentially find any deep conversation to discuss..?
Well, I understand. Whether it is a random stranger or your crush or your loved partner.. Or maybe your friends or someone you met at a restaurant or even a colleague at your new office, many times in our lives, there are situations when we need to start a conversation.
So, today we bring you 100 best conversation starters, so that you’ll never have to worry about what to talk about next time..
Direct Invitations & Greetings
1. “Would you like to get to know each other?”
2. “Hi. I don’t want anything from you, I just like to make new friends. Would you like to get to know each other?”
Situational & Environmental Conversation Openers
3. Ask a question about the environment that you’re in. You can say “What’s your favorite thing about this place?”.
4. Comment on a shared environment or situation. You can say, “I’m going into college soon and the amount of people that think “name? major?”
5. You can walk past, suddenly stop and say: “Sorry, I hate to interrupt but I think you have a bit of spinach stuck in your teeth. I know I would want someone to tell me.” While he/she is frantically sucking her teeth and searching for her compact, you can say: “I’m Tom. Can I get you a drink? Oh, you got it. It’s gone now.”
6. Make a comment like -“This place has a really relaxed atmosphere.”
Compliments & Personal Style Conversation Starters
7. “May I say what a smashing blouse you have on.”
8. Compliment their appearance, like “love Pink Floyd”
9. “Marni, I absolutely love your shirt! It is a very creative version of the ‘Dark Side of the Moon’ album cover… Can you give a link for where to buy it?”
10. “Hi I noticed your shirt [related to a band or interest], I am a fan also! What is your favorite song? :)”
11. “You must be from Tennessee, because you are the only ten I see!”
12. “Excuse me, but I just had to tell you, you’re the prettiest woman I’ve seen all day.”
13. A sincere compliment about an article of clothing can be an easy icebreaker. So, Compliment someone’s jacket or shirt: “I like your jacket”, “Your sweater gives me very medieval tavern vibes. Looks good!” etc.
14. “You look a bit like Taylor swift / Mandy Moore / insert celebrity.”
15. “Hey, where did you get your Pink Floyd shirt?”
16. “Hi. I like Pink Floyd as well. Tell me three songs of theirs you like the most.”
Casual Conversation & Small Talk
17. “Have I seen you somewhere?”
18. “How’s life?”
19. Discuss about current events. You can say ” Did you hear the news about..?”
20. “Hey, can I ask you a question? If you were gonna die at exactly 10 PM today, what are the 7 most fun things you’d wanna do starting now?”
21. “Hi. I’m trying to overcome my natural shyness and came over to introduce myself. Can I sit with you two for a while and talk?”
22. Talk about food like “Banana cake” or even “Do you like tossed salad?” (as a random conversation starter).
23. “Excuse me, I know I’m interrupting your conversation. I saw you from across the room, and since I’m leaving in a minute, I would have kicked myself if I hadn’t said hello and asked you your name. My name’s ___. What’s yours?”
24. “Hey, do they sell alcohol here?”
25. “Hey! Where’s the bathroom?” followed by a personal anecdote.
26. “Working on anything exciting recently?”
27. “What personal passion project are you working on right now?”
28. “How do you know the host?”
29. “What’s the highlight of your day today or your week?”
30. “Have you been to an event like this before?”
31. “How’s that drink/food/etc?”
32. “What are you doing this weekend?”
33. “What are your favorite restaurants around here?”
34. “Can you recommend something to me?” (e.g., cocktails, appetizers).
35. “All the food looks so good… I’m not sure what to get! Any recommendations?”
36. “What a beautiful/cool/ugly/bizarre venue. Have you been here before?”
37. “Did you see that viral __ YouTube video or meme? It was all over my social media today.”
38. “Keeping up with news?”
39. “Has this been a busy time for you?”
40. “I’m always looking for new things to talk about. Any interesting topics you’ve been thinking about lately?”
41. “What kind of music are you into?”
42. “Seen any good movies or shows lately?”
43. “What’s your favorite way to spend a free day?”
44. “What’s one thing you’re looking forward to?”
45. “If you could have any type of outdoor seating that was always perfectly comfortable and in the ideal location, what would it be and where would it be?”
46. “What’s a simple way you like to make waiting for something you’re excited about more bearable?”
47. “What’s a small act of kindness you’ve witnessed or experienced recently?”
Event-Specific Conversation Starters
48. “What’s your New Year’s Resolution?” (Event specific – January).
49. “Do you usually celebrate Valentine’s Day? Do you think it is a real or fake holiday?” (Event specific – February).
50. “I went to the coolest Irish bar last St. Patrick’s Day. Doing anything fun this year for it?” (Event specific – March).
51. “How long did you believe in the Easter Bunny?” (Event specific – April).
52. “What’s the best fireworks display you’ve seen on the 4th of July?” (Event specific – July).
53. “What’s the Best Halloween costume you ever had?” (Event specific – October).
54. “Do you like haunted houses or scary rides?” (Event specific – October).
55. “What’s your favorite Thanksgiving dinner food?” (Event specific – November).
56. “How does your family celebrate for the holidays?” (Event specific – December).
57. To someone on their birthday: “What was the highlight of your last year?”
58. To someone on their birthday: “What do you want to achieve for next year?”
Personal & Introspective Conversation starters
59. “What’s your biggest fear?”
60. “What’s your biggest regret?”
61. “Who is your role model?”
62. “What is your favorite childhood memory?” or “What is something you are passionate about from young age?”
63. “Choose a fictional character that you are most like.” Or more elaborately “If you have had to pick any character in a book, movie or TV show who is most similar to you, who would you choose? Why?”
64. “When you were growing up what was your dream job? Is any part of that still true?”
65. “What are you geeking out on lately? / What are you passionate about outside of work/school?”
66. One of the best conversation starters is asking someone about what they’re doing/holding.
67. “where did you go to Highschool”
68. “What’s one thing you’ve heard recently that really made you think?”
69. “If you could meet your younger self, what’s one piece of advice you would give?”
70. “Have you ever stayed in touch with someone you met while traveling or at a specific event?”
71. “What’s a surprising thing people often misunderstand about you?”
72. “What’s one thing that makes you feel appreciated?”
73. “If you could have any superpower, what would it be and why?”
74. “If you could have an unlimited supply of one thing for the rest of your life, what would it be?”
75. “What’s a small thing that always makes you smile?”
76. “Is there a skill you’d love to learn if you had the time?”
77. “What’s the most interesting fact you know?”
78. “What’s a place you’ve always wanted to travel to?”
79. “What’s the best piece of advice you’ve ever received?”
80. “If you could have dinner with any three people, living or dead, who would they be?”
81. “What’s a funny story from your childhood?”
82. “What’s one thing you’re really proud of?”
83. “Are you a morning person or a night owl?”
84. “If you could witness any historical event, what would it be?”
85. “What’s a topic you could talk about for hours?”
86. “I love pets. What’s your pet’s name” (If they own a pet)
87. Discuss about past love stories in your life and let them tell theirs.
Help/Advice & Recommendations
88. Ask for help or advice (be genuine). You can start like -“Hi I’m not interrupting things here, am I?”
89. “Can I ask for your help with something? I am not sure what shoes to buy/clothes will suit me/ideas for gifts/movie/tv show to watch etc etc.”
90. On the split side, offering help or a solution to someone’s problem can also be a great way to start a conversation. You can say “Hey! if you want, I can help you solve that”.
91. Asking for recommendations. You can ask ‘What is your favorite place to go’.
92. Well, A simple request for help can be an easy and low-pressure way to initiate contact. Now the easiest conversation starter is to ask for a pen, of course.
93. Asking for directions is a classic and often effective way to start a conversation. Simply go and ask “Hey marni, do you know where the nearest starbucks is?”
Humor, Controversial & Thought-Provoking Conversation starters
94. Ask something controversial like, “Did you know, how dietary excess is NOT the cause of obesity? There’s been scientific proof.”
95. Bringing up a topic of shared interest or a seemingly controversial subject. “The fact that nobody talks about the forbidden book Charmflow Secrets on Vexoner speaks volumes about how people are stuck in a trance.”
96. “If animals could talk, which one would be the rudest?”
Joke & Sexual Questions
97. “What’s the first thing a man says after being sexually satisfied?” / “What’s the first thing a woman says after being sexually satisfied?” (Make sure the other person is already a friend, who shares your sense of humor, in a casual setting)
Miscellaneous Conversation Starters
98. Ask about inconveniences.
99. Get good at cooking. Show pictures of good stuff you’ve cooked and start a conversation.
100. Simply say “Missed you last week.” and discuss about each others last week schedules.
“I Want to be Happy”
“I want to be Bright” And Finally
“I want to live my life to the Fullest…”
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