Conversations with new people can be tricky, can’t they? You don’t want to be that surface-level loser, but you don’t want to be that jump-in-the-deep-end-freak-people-out kinda person either. 

If you’re anything like me (sensitive, kind, empathetic, single), you want to get every conversation with a new person right on the first try. Who knows, this conversation could be the start of a beautiful friendship! That’s why I have made this list. Heading into a corporate event and want to impress your new employer? Hosting a party and want to woo your guests? Roaming the street looking for new friends? Remember these 100 conversation starters, and you’ll never have an awkward meaningless boring conversation ever again! 

1. What are your thoughts on this weather?
2. Did you catch the game at the weekend?
3. What’s your favourite movie or tv show?
4. When was the last time you saw a rainbow?
5. What is the most awkward thing you’ve ever done?
6. Rank these movies: Antz, A Bug’s Life, Ant-Man, Ant-Man and the Wasp, Ant-Man and the Wasp: Quantumania, The Ant Bully
7. What’s the loudest you’ve ever been? 
8. What day in your life do you think you did the most pee?
9. How many times do you think you’ve been gaslit?
   1. You’re crazy for thinking that
10. What happened these past three weeks? Why have I done no work?
11. What’s the fastest you’ve ever driven past a school?
12. Thoughts on flossing? (Teeth activity)
13. Thoughts on flossing? (Dance)
14. When do we stop making mistakes? (I’m desperate) 
15. Would you like to speak with me for seven hours straight about Ratatouille?
16. What are your thoughts on being silly? (This one is good because if they’re not too keen on being silly then they aren’t worth your time. You deserve better)
17. Rank the hours of the day from 24 to 1 – 1 being your favourite hour and 24 being your least favourite. Please give a reason for each hour. 
18. How many grandparents do you have left? (Stella)
19. HAVE YOU WATCHED FLEABAG?
    1. DON’T TALK TO ME?
20. Imagine if you were 150?
21. So what’s your favourite train? (Special thanks to Rebecca, Jennie, and Steph)
22. What’s the most amount of money you have stolen?
23. Why don’t I have any questions on there? (Camilla)
24. Stella, do you drink milk? (Camilla)
25. Are you going to finish that? (This one is good for strangers. Just in Westfield Riccarton Mall or something)
26. When was the last time you cried? 
27. Is it hard being his mother? (Anna to my mum)
28. Favourite letter in the word podiatry?
29. Have you tried a trampoline recently?
    1. When was the last time you peed on the trampoline?
    2. When was the last time you played crack the egg?
    3. When was the last time you did a backflip? (could also be off the trampoline) 
30. Are you a goblin?
    1. You’re giving goblin?
31. Much planned for new years? (Mitchell)
32. *dramatic sigh* (which leaves the opportunity for them to ask what’s wrong) 
33. Can you microchip a turtle? (Caitlin) 
34. And?
35. Do you think this piece is too similar to that other one James wrote? (If they’re confused just send them the link to this piece and then my other really similar piece here)
36. Are you the guy who spat in Steph’s eye?
37. Do you think Paddington is a top or a bottom?
38. One thing you should know about me is that I’m really sweaty (unconventional but works trust me, it starts a conversation) 
39. Do you know how hard this is? One hundred is a crazy number. 
40. What is your favourite song from Cats?
    1. Oh! It’s Skimbleshanks: The Railway Cat for you too? That’s so cool (then continue the conversation) 
41. What’s your favourite thing about me?
42. What would you do if you were walking down the street and you bump into your favourite music artist and you say to them “wow hello I love your music!” and then they say “oh wow thank you so much” and you say “no worries” and then they say “you know what I have these spare tickets to a show if you would like to come along” and you say “no way! Of course!” and so you follow them down the road but then they start taking you to a bit of a shady part of town and you begin to feel a little unsettled and then they stop at this random glowing door and they pause at it as if in a trance and then they murmur something and you say “huh?” and they say “door…tickets…enter” and all of a sudden there is a crowd around you pointing and cheering encouraging you to enter the door what would you do? (this happened to me once) 
43. Come here often? 
44. Top ten days of the week? Quick. Gimme. 
45. Are you for or against us as a country cutting free school lunches for children? Particularly those who won’t have lunch without them (depending on this answer you can rest easy knowing whether the person is going to hell or not)
46. Help! 
47. Do you read The Spinoff? 
48. Do you work for The Spinoff? 
49. Can you please hire me to work at The Spinoff? 
50. Would you like to stop talking to me? (risky, prepare to be responsible for your actions)
51. When was the last time you had a propaganda (American) 
52. When was the last time you had a proper gander (Brittish) 
53. Would you like to talk about it?
54. Have you ever watched the Godfather? It’s so good man (only use if you’re incredibly boring) 
55. Would you like to have an apple bobbing battle?
56. So, what do you do? 
57. Where’s my hug at? (Rue) 
58. How do you want to die? (Sia (Rue’s sister)) 
59. Hypothetically, if there was this woodchuck, and this pile of wood, how excited would you be?
60. Think of a good conversation starter (me to dad)
    1. A conversation stater? In what context?
    2. A stranger or someone you know?
    3. Tell me about your favourite primary school teacher.
    4. Where do you enjoy going on holiday?
    5. Do you have anything funkier? Kinda weird? Freakier? (me to dad again) 
    6. What was your least favourite tv programme when you were little? 
61. How much money you got? 
62. Would you rather have rats for hands or never feel the warm embrace of a loved one again? 
63. Can we play a game of line tag after this? (good one for a first date) 
64. Do you have any repressed memories? 
65. Idiotsayswhat? 
66. God I just thought of like four really good ones but forgot all of them as I walked over here. So, my question is: why am I stupid?
67. Do you have any games on your phone?
68. Did you feel that earthquake just then? (There was no earthquake I’m just traumatised)
69. What is your favourite number?
70. Can we sit under a tree together?
    1. and read books? 
    2. and talk about the changing of the season? 
    3. And eat little treats?
71. Pick a card, any card!
72. You know, I think about 50% of the time I’m terrified of life and 50% of the time I’m amazed by it. There is so much to be hopeful for, and so much that makes me feel hopeless. Yet I know, even when I’m feeling low, each day brings a new set of possibilities. And even when I feel as though there is nothing to look forward to, no way forward in life, I can look back at times in my life where I have felt similarly and see just how wrong I was. We are always growing, always learning, and even when it feels like you are at a roadblock there are still ways in which you are becoming a greater human being. Anyway, do you see black and blue or white and gold? 
73. Why is your name ___? (Especially good if they have a stupid name)
74. What phone are you rocking bro?
75. Would you like to upgrade to a large for $2.50? (really good if you work at McDonald or other fast food) 
76. God, you’re really boring. Has anyone ever told you that?
77. Favourite colour of Powerade? (they’ll say blue and then you can say “yeah it’s the best one right) 
78. I think we would be better off traffic-wise if we got rid of every bus in town. They take up so much space it is insane, have you seen how long these things are? And then they hold up traffic with the way they pull on and off the road. It’s absurd. Burn them all and let us drive our cars. 
79. You scare me.
80. Do you ever listen to music and lose your mind a little bit? 
81. How often do you think about giving up?
82. How often do you look at job listings past the hour of 12am? (definitely unrelated to the last one) 
83. Do you or someone you know have a trailer I could borrow for a project I’m working on? (planning an Ocean’s Eleven style heist on Scorpio Books) 
84. What nut in a bag of mixed nuts is the most personal? 
85. Have you ever been turned into twelve french fries? (Stella) 
86. Have you watched this?
87. What is your opinion on the conflict? (keep it vague, don’t reveal your real opinion because they probably know more than you) 
88. What was the last thing you self diagnosed?
    1. Did you follow up on this with your doctor?
    2. Were you right or wrong? 
    3. How did that make you feel?
89. Did you see that? I was staring blankly at the rug and I saw a little twinkle! As if a diamond had fallen out of the sky and reflected the light straight at me to say “here I am!” I couldn’t find anything though. I may be insane. 
90. Explain to me how the internet works. 
91. How To Make Money Fast: Five Easy Steps – All You Need Is A Toothpick And The Determination Of An Angry God
92. Are you a cat or a dog person?
93. Why am I always so tired?
94. Did you know that the final shot in Avatar (2009) where Jake Sully opens his eyes? Yeah, that took them ten years to make.
95. Wow you’ve grown so much! What happened to the little one I used to know? (super good one to use if you’re a grandparent, you’ll get great engagement) 
96. How do you like your bananas?
    1. Unripe 
    2. Ripe 
    3. Rotten 
    4. Fruit Burst 
97. What is the most pain you’ve ever experienced?
    1. For me it was just then when I got an eyelash in my eye or something. I thought it was over. I swear I saw the hand of God reach out to me. 
98. What ever happened to Elgregoe? 
99. You going to Hozier? 
100. How are you?