If you grew up with cousins, you probably know they’re the built-in friends you didn’t exactly choose but couldn’t imagine life without. Some are practically siblings. Others are more like mystery relatives you only see at weddings and holiday dinners. But no matter your cousin dynamic, catching up with them can be such a good time especially when you have the right questions on hand.

As a wellness and growth blogger (and yes, someone who’s obsessed with making conversations more meaningful), I’m always collecting thoughtful, unexpected, and honestly fun questions to spark connection. Whether you’re planning a cousins only Zoom call, game night, reunion, or just want to deepen your bond with the fam, this list is for you.

So if you’re tired of the usual “How’s work?” and “What have you been up to?” questions, you’re in the right place. These 100 catch-up questions go deeper and sillier and give you all the tools to really reconnect.

And yes, I’ve added some recommendations to make your cousin catch-up time even more memorable, whether you’re journaling these answers, doing a game night, or planning your next hangout.

Related post: 100 “Would You Rather” Questions for Game Night with Cousins.

How to Use These Questions

• Pick a few and text them to your cousin.
• Play a “cousin connection” game at the next family get-together.
• Use them as journaling prompts to reflect on your relationship.
• Bring them on a road trip, brunch date, or cousins only vacation.

Wherever or however you use them, these questions are designed to bring out stories, laughs, and those “I totally forgot about that!” moments.

100 Catch-Up Questions for Cousins

1. What’s your all-time favorite memory of us growing up?
2. What family tradition do you secretly love?
3. Who do you think is the most dramatic person in our family?
4. What’s the weirdest thing that ever happened at a family gathering?
5. What’s a random talent you have that no one knows about?
6. If we started a cousin group chat, what would it be called?
7. What’s your current comfort show or movie?
8. If our lives were a reality show, what would be the title?
9. What’s something you’ve always wanted to ask me but never did?
10. Which family member do you think you’ve become more like over time?
11. What’s something you admire about our grandparents?
12. What’s one childhood game or toy you’d bring back in a heartbeat?
13. What’s your go-to karaoke song?
14. What’s the wildest dream you’ve had recently?
15. If we took a cousin trip, where should we go?
16. What’s your weirdest food combo that actually slaps?
17. Who was your childhood crush (TV or real life)?
18. What’s something you wish our family did more often?
19. What’s your most unpopular opinion?
20. If we swapped lives for a day, what would I struggle with the most?
21. What’s the biggest glow-up you’ve had?
22. What’s your current obsession (snack, app, trend)?
23. What’s the last thing that made you laugh way too hard?
24. What’s one thing you’re proud of but never brag about?
25. What memory of us makes you laugh out loud every time?
26. If you had to cook dinner for the whole family, what would you make?
27. What’s something you’ve learned about yourself this year?
28. Who in the family always gives the best advice?
29. What’s your go-to way to cheer yourself up?
30. What’s your hidden superpower?
31. What’s one thing you’d love to do together again from childhood?
32. What’s a song that instantly reminds you of me?
33. What’s something that makes you feel nostalgic lately?
34. Who in the family would win a cooking competition?
35. What would be your dream cousin group business?
36. What’s one thing you’ve always wanted to learn but haven’t yet?
37. If we had a cousin talent show, what would you perform?
38. What’s your love language these days?
39. What’s one piece of advice you’d give your younger self?
40. What’s your go-to self-care ritual right now?
41. What was your first ever job, and how did you feel about it?
42. If you had to choose a movie character to describe me, who would it be?
43. What’s something you thought was normal in our family but later realized was unique?
44. Who would win at family trivia night?
45. What’s one thing you’re currently healing from?
46. What was the best vacation you’ve ever taken?
47. What’s something about adulthood that still surprises you?
48. Who in the family do you wish you could talk to more often?
49. What’s something small that made your day recently?
50. What’s your idea of a perfect Saturday?
51. What was the most rebellious thing you did as a teen?
52. What’s your dream for the next 5 years?
53. What’s something new you’ve tried lately?
54. What’s the best piece of advice you’ve ever received?
55. If you could relive any age, which one and why?
56. What’s a random family story you wish was recorded on video?
57. What’s your ultimate go-to comfort meal?
58. Who in the family always knows how to get out of trouble?
59. What’s your current morning or night routine like?
60. If we wrote a book about our cousin memories, what would the title be?
61. What’s one thing you miss about childhood?
62. What’s something fun we should do before the end of the year?
63. Who’s the best storyteller in the family?
64. What’s your guilty pleasure right now?
65. What’s a family inside joke you’ll never forget?
66. What kind of legacy do you want to leave behind?
67. What’s one thing you never told your parents growing up?
68. What’s something that gives you butterflies (in a good way)?
69. If we created a family time capsule, what would you put in it?
70. What’s one thing you want to unlearn?
71. What’s something you’re super passionate about lately?
72. What’s one boundary you’ve created that has changed your life?
73. What’s your “power outfit” and how does it make you feel?
74. What’s one thing you’re surprisingly good at?
75. What’s a cause you care deeply about?
76. If you could master one skill instantly, what would it be?
77. Who in the family could easily go viral on TikTok?
78. What’s your personal theme song right now?
79. What’s your proudest moment so far this year?
80. What do you think makes our cousin bond special?
81. What’s something you thought you’d have figured out by now?
82. What does “success” look like for you today?
83. If you could redo one moment with better confidence, what would it be?
84. Who was your biggest childhood role model?
85. What’s your favorite family meal?
86. What would you name a cousin group podcast?
87. What’s something you’ve let go of recently?
88. What’s your love story—messy or magical?
89. What’s your idea of “living your best life”?
90. What’s your current definition of happiness?
91. What’s one tradition you’d love to start with just us cousins?
92. What’s one fear you’ve conquered?
93. What’s your current phone wallpaper and why?
94. What makes you feel most like yourself?
95. Who do you turn to when life gets real?
96. What’s something you think people misunderstand about you?
97. What’s your happy place—real or imagined?
98. What’s your go-to hype song?
99. What’s one thing you’ve changed your mind about recently?
100. What’s something you want me to remember about you?

Recommendations for the Ultimate Cousin Catch-Up Time

Want to make your cousin connection time extra special? These Amazon finds are so worth checking out:

• “We’re Not Really Strangers: Family Edition” – Deepen your cousin conversations with this card game designed to get past the small talk.
• The “Cousin Crew” Matching Shirts or Mugs – Because yes, matching cousin merch makes everything more fun.
• Promptly Journals – Conversations With Family – Great for capturing those stories you never want to forget.
• Portable Phone Tripod with Ring Light – For your next cousin TikTok or cozy Zoom game night.
• “Truth or Drink: Family Pack” – If you’re feeling bold and ready to level up game night.

Final Thoughts

Reconnecting with cousins doesn’t have to be awkward or surface level. These 100 catch-up questions are your invitation to get real, laugh harder, share memories, and deepen your bond with the people who’ve known you through every weird and wonderful family phase.

Whether you’re catching up over text, FaceTime, or during your next cousin getaway, let this list be your go-to guide to real, fun, and unforgettable convos.

So, which question are you asking first?