Smiles are contagious, don’t you think? Sometimes all it takes is the right question to make someone light up, laugh out loud, or remember something sweet they hadn’t thought about in years. Whether you’re spending the night with friends, going on a date, hanging out with family, or just trying to brighten someone’s day, the right kind of playful, thoughtful, or silly questions can work wonders.

And because I’m all about helping you create meaningful and joy-filled connections, I put together 100 unique questions you can ask to make someone smile. These aren’t your usual overused “What’s your favorite color?” or “What’s your dream job?” kind of questions. Nope. These are fun, quirky, heartwarming, and downright silly questions that actually get people to loosen up, laugh, and share.

Before we dive into the list, here’s a little tip: keep a cute notebook or journal nearby where you can jot down funny answers and memories. I personally love the Promptly Conversation Journal or a simple Moleskine Classic Notebook (both on Amazon) because it feels extra special to have a keepsake of your laughter-filled nights. Find more conversation starters here.

Now, let’s get into the good stuff, your stash of 100 smile-sparking questions.

100 Questions to Ask to Make Someone Smile

Silly and Playful

1. If your pet could talk, what would they roast you about first?
2. What’s the most ridiculous excuse you’ve ever come up with on the spot?
3. If you had to rename yourself after your favorite snack, what would it be?
4. Which cartoon character would totally babysit you better than your parents did?
5. If you could only wear one silly hat for a year, what hat would you pick?
6. What’s the weirdest but funniest nickname you’ve ever been given?
7. If you opened your own amusement park, what silly ride would be the star?
8. What’s your go-to funny face when you want to make a kid laugh?
9. If you were a kitchen utensil, which one would you be and why?
10. If you could prank any celebrity without consequences, who would you choose and how?

Wholesome and Heartwarming

11. What’s the nicest compliment that still makes you smile when you think about it?
12. Can you remember a tiny kindness that changed your whole day?
13. Who in your life can make you laugh without saying a word?
14. What memory always warms your heart no matter how long ago it happened?
15. If you could bottle up a single moment of happiness, what would it be?
16. What’s the funniest childhood memory your family still teases you about?
17. Who was your childhood best friend, and what silly thing did you do together?
18. If you had to dedicate a funny song to your best friend, which one would it be?
19. What’s the most random inside joke you still laugh about?
20. Who is the most unexpectedly funny person you know?

Quirky “What If”

21. If you had to speak only in song lyrics for a day, which artist’s lyrics would you use?
22. If you woke up with a tail tomorrow, what’s the first thing you’d do?
23. If laughter was money, what’s the “richest” you’ve ever been?
24. What would happen if you swapped lives with your 10-year-old self for a day?
25. If you could star as the funniest character in any sitcom, who would you be?
26. If you could invent a holiday based only on laughter, what would you call it?
27. What’s the most laughable superpower you can imagine?
28. If your thoughts came out as subtitles over your head, how much trouble would you be in?
29. If animals opened comedy clubs, which animal would be the best comedian?
30. What silly law would you make if you were president for a day?

Food and Fun

31. What’s the funniest food accident you’ve ever had?
32. If pizza could talk, what would it say to you right now?
33. What’s the weirdest food combo you secretly love?
34. If you could only eat snacks shaped like animals, which one would you start with?
35. What’s the most dramatic reaction you’ve ever had to tasting something new?
36. Which dessert do you think would tell the best jokes?
37. If you were an ice cream flavor, which one would you be and why?
38. What’s your funniest memory involving birthday cake?
39. If you were a breakfast cereal, what would your mascot look like?
40. What’s one food you can never eat with a straight face?

Just for Laughs

41. If you had a laugh track following you everywhere, what would it sound like?
42. What’s the most random thing that ever made you burst into laughter?
43. If you had to make your old teacher laugh, what would you do?
44. Which emoji secretly represents your laugh?
45. What’s the funniest autocorrect fail you’ve ever sent?
46. Who would win a joke battle—you or your best friend?
47. Have you ever laughed so hard at something you couldn’t even explain why?
48. What’s your go-to funny story to tell when a room gets quiet?
49. If laughter added years to your life, how long would you live?
50. What’s your favorite so-bad-it’s-good joke?

Nostalgic and Sweet

51. What’s a childhood TV show moment that still makes you smile?
52. Did you ever believe something silly as a kid that you laugh about now?
53. Who taught you the funniest lesson when you were younger?
54. What school memory makes you grin every time you think about it?
55. Did you ever have a silly “fashion phase” you secretly loved?
56. What’s your favorite funny memory from a family gathering?
57. What’s the best birthday surprise you ever got?
58. Did you have a childhood imaginary friend? If so, what were they like?
59. What’s the funniest memory from a school trip or vacation?
60. What’s one tradition in your family that always made you smile?

Randomly Fun

61. If you could swap laughs with someone, whose laugh would you want?
62. What’s your guilty-pleasure movie that makes you laugh every time?
63. Which animal do you think has the most contagious laugh?
64. If you had to create a silly new sport, what would it be?
65. Which board game always brings out the most laughter for you?
66. What’s the funniest commercial you’ve ever seen?
67. If you had a comedian alter ego, what would your stage name be?
68. What’s your funniest karaoke memory?
69. What’s the weirdest place you’ve ever laughed uncontrollably?
70. Which toy from your childhood still makes you grin to think about?

Deep but Lighthearted

71. What’s the best advice you’ve heard that made you smile instantly?
72. What silly thing always cheers you up no matter what?
73. What’s a song lyric that makes you laugh every single time?
74. Which movie character would be your funniest best friend?
75. What’s one thing that never fails to give you the giggles?
76. Who’s the funniest family member you’ve ever had?
77. If you had to laugh at the same joke forever, which one would you choose?
78. What’s the funniest compliment someone has ever given you?
79. What’s the best prank you’ve ever seen or pulled?
80. What funny thing makes you feel instantly closer to people?

Out-of-the-Box

81. If you could only laugh in animal sounds for a day, which animal would you choose?
82. Which celebrity do you think would be the worst at telling jokes?
83. What’s the funniest outfit you could imagine wearing to a wedding?
84. If laughter was a perfume, what would it smell like?
85. What’s the weirdest dream that made you laugh when you woke up?
86. Which historical figure do you think had the best sense of humor?
87. If you had to dance every time you laughed, what dance would it be?
88. Which fictional world would have the funniest comedy shows?
89. If laughter was visible, what color would yours be?
90. What’s the most random thing that makes you laugh every time?

Final Ten for the Fun Nights

91. What’s the most dramatic way you’ve ever told a funny story?
92. Who’s the last person who made you laugh so hard you cried?
93. If you could trade your laugh for a celebrity’s laugh, whose would you pick?
94. What’s one joke you secretly love even if no one else does?
95. What’s the funniest ringtone you’ve ever heard?
96. Who do you think in this room would win a comedy award?
97. What’s your funniest memory from a sleepover or late-night hangout?
98. If you could turn any object into a comedian, what would you choose?
99. What’s the most unexpected thing that’s ever made you giggle?
100. What’s your personal definition of a “happy laugh”?

Amazon Favorites for a Fun Conversation Night

Want to make your night even cozier while you go through these questions? Here are a few Amazon finds I personally love:

• TableTopics Original Edition – a card deck of fun prompts that get everyone laughing.
• Moleskine Classic Notebook – the perfect journal to jot down funny answers.
• Bedsure Fleece Throw Blanket – soft and cozy for those long laughter-filled nights.
• Bamboo Snack Board – because snacks are a must when you’re talking and laughing for hours.

A good laugh can shift the energy of the entire evening. With these 100 questions, you’ll have plenty of ways to bring joy, spark connection, and make memories that stick. Whether you’re on a fun night with friends, curled up with your partner, or hanging out with family, these questions are little keys to unlocking happiness.