There’s something magical about best friends. They’re the ones who know our secrets, celebrate our wins, and offer a shoulder to cry on during tough times. But even with your BFF, conversations can sometimes fall into the routine of “How’s your day?” or “What’s new?” If you’re looking to take your friendship to a deeper, more fun level, you’re in the right place!

In this blog post, I’ve curated 100 fun and unique questions to ask your best friend. These aren’t your usual “What’s your favorite color?” type of questions. Instead, they’re designed to spark laughter, uncover hidden stories, and strengthen your bond.

I’ll also recommend some cute Amazon finds to make your hangouts extra special, whether it’s a cozy night in or a fun adventure together. Let’s get started!

Why Fun Questions Matter in Friendships

Asking thoughtful, playful questions can:

• Strengthen your connection by uncovering shared experiences or dreams.
• Create hilarious moments you’ll cherish forever.
• Help you learn more about your bestie (even if you think you already know everything!).

Friendships thrive on communication and shared joy, and these questions are the perfect way to keep things lively and fresh.

Recommendations to Elevate Your Bestie Bonding Time

• Friendship Journals: Try the Knock Knock Bestie Journal for fun prompts you can fill out together.
• Matching Accessories: These Best Friend Necklaces are a sweet way to celebrate your connection.
• Game Night Fun: Grab a deck of Our Moments: Girls Night Out for even more hilarious conversation starters.

100 Fun Questions for Best Friends

Childhood Memories

1. What’s the most embarrassing thing you remember doing as a kid?
2. Did you ever have an imaginary friend? If yes, what were they like?
3. What was your most epic Halloween costume growing up?
4. Did you ever get in trouble at school? What for?
5. What’s one toy or game you were obsessed with as a kid?

Dreams and Aspirations

6. If money wasn’t an issue, what’s the first thing you’d do tomorrow?
7. What’s a childhood dream you still secretly think about?
8. If you could live anywhere in the world, where would it be and why?
9. What’s one skill you wish you could master overnight?
10. If you could open any kind of business together, what would it be?

Pop Culture and Entertainment

11. If your life were a TV show, what genre would it be?
12. Which celebrity do you think would play you in a movie about your life?
13. What’s the most random fun fact you know about a celebrity?
14. If you could hang out with one fictional character, who would it be?
15. What’s a guilty pleasure TV show or movie you secretly love?

Funny and Lighthearted

16. What’s the most ridiculous thing you’ve ever done to impress someone?
17. Have you ever made a terrible fashion choice you thought was cool at the time?
18. What’s your most unforgettable awkward moment?
19. If we were stuck in an elevator, what’s the first thing you’d do?
20. What’s the weirdest or funniest nickname you’ve ever had?

Friendship Memories

21. What’s your favorite memory of us hanging out together?
22. What’s the funniest inside joke we’ve ever created?
23. If we had a theme song for our friendship, what would it be?
24. What’s one trip we’ve taken together that you’ll never forget?
25. What’s something you appreciate about me that you’ve never told me?

Food and Drink

26. If you could eat only one dessert for the rest of your life, what would it be?
27. What’s the weirdest food combination you’ve ever tried?
28. What’s your go-to comfort food?
29. If we could create our own signature cocktail, what would we call it?
30. What’s the most over-the-top meal you’ve ever had?

Personality and Quirks

31. What’s one thing you do that instantly makes people laugh?
32. If you could change one thing about yourself, what would it be?
33. What’s a quirky habit you have that no one else knows about?
34. What’s your most random pet peeve?
35. What’s something super weird about you that you’re secretly proud of?

Travel and Adventure

36. What’s the most adventurous thing you’ve ever done?
37. If we could take a road trip anywhere, where would we go?
38. Have you ever been totally lost on a trip? What happened?
39. If you could teleport anywhere in the world right now, where would it be?
40. What’s one travel experience you’ll never forget?

Style and Fashion

41. What’s your go-to outfit when you want to feel confident?
42. What’s one trend you’ll never try, no matter how popular it gets?
43. If you could swap wardrobes with anyone, who would it be?
44. What’s the most expensive thing you own that was totally worth it?
45. What’s a fashion risk you’ve always wanted to take?

Relationships and Love

46. If your love life were a rom-com, what would it be called?
47. What’s the worst date you’ve ever been on?
48. If you could create the perfect first date, what would it include?
49. What’s the funniest or most awkward pickup line you’ve heard?
50. What’s one relationship lesson you’ve learned the hard way?

Imagination and “What Ifs”

51. If we switched lives for a day, what’s the first thing you’d do?
52. If you could time travel, what era would you visit?
53. What would you do if you won the lottery tomorrow?
54. If animals could talk, which one would you have as a sidekick?
55. If you could relive one day in your life, which would it be and why?

Music and Creativity

56. What’s your ultimate karaoke song?
57. If you could learn to play any instrument instantly, what would it be?
58. Who’s your favorite underrated musician or band?
59. What’s one creative project you’ve always wanted to try?
60. If you had to describe yourself using three songs, what would they be?

Serious but Sweet

61. What’s one piece of advice you’d give your younger self?
62. What’s one thing you’ve never done but want to try with me?
63. How do you define happiness?
64. What’s something you’re really proud of but don’t talk about often?
65. What’s a fear you’ve overcome that changed your perspective?

Games and Challenges

66. If we made up our own holiday, what would we celebrate?
67. What’s one challenge you think we could crush together?
68. What’s a dare you’d never back down from?
69. If we competed on a game show, what would our team name be?
70. What’s a prank you’ve always wanted to pull on someone?

Future Dreams

71. What’s one crazy dream you think we could actually pull off together?
72. Where do you see us 10 years from now?
73. What’s one thing you hope we’ll never stop doing as friends?
74. If we could plan the ultimate “best friend day,” what would it include?
75. What’s one goal you’re working on that I can help with?

Make It Fun and Memorable

Friendship is one of life’s greatest gifts, and nurturing it with fun questions is a simple but meaningful way to keep the connection alive. Whether you’re chatting over coffee, on a road trip, or just texting, these questions will spark laughter, deepen your bond, and create unforgettable memories.

Here’s to countless laughs and new adventures with your bestie!