We all have that one friend—we were once inseparable, but then life got busy. Maybe they moved away, maybe work and responsibilities took over, or maybe it was just one of those “Let’s catch up soon!” texts that never actually happened. But now, you’re finally meeting up.

And while you’re excited, you also don’t want the conversation to feel forced or surface-level. You want to truly reconnect and to go beyond the usual “So, how’s life?” and really dive into what’s been happening in each other’s worlds.

That’s why I’ve put together these 80 fun, meaningful, and unique catch-up questions to help break the ice, spark deep conversations, and make your time together unforgettable. Whether you’re grabbing coffee, FaceTiming, or just texting, these questions will ensure your catch-up session is full of laughter, nostalgia, and genuine connection.

80 Catch-Up Questions for a Friend You Haven’t Seen in a Long Time.

General Life Updates

1. What’s the biggest change in your life since we last talked?
2. Have you picked up any new hobbies or passions?
3. If you had to describe the past year in three words, what would they be?
4. What’s been your happiest moment since we last met?
5. Have you traveled anywhere exciting lately?
6. What’s a new daily habit or routine that’s improved your life?
7. Have you moved, changed jobs, or made any major life decisions?
8. What’s one unexpected thing that happened to you recently?
9. What’s something you never thought you’d do, but ended up doing?
10. How do you usually spend your weekends these days?

Fun & Nostalgic Questions

11. What’s a funny or embarrassing memory from our past that still makes you laugh?
12. If we could time travel back to one of our best moments together, which one would it be?
13. What’s the wildest thing you’ve done since we last talked?
14. Have you tried any TikTok or viral internet trends?
15. What’s your go-to guilty pleasure TV show or movie?
16. If your life were a movie, what would the title be right now?
17. What’s the most ridiculous thing that has happened to you recently?
18. Have you come across any old photos or messages of us that made you nostalgic?
19. What’s one inside joke we have that still makes you laugh?
20. If we had a reality TV show, what would it be called?

Personal Growth & Self-Discovery

21. What’s something new you’ve learned about yourself recently?
22. Have you had any big mindset shifts over the past year?
23. What’s a piece of advice you’ve heard recently that really stuck with you?
24. Have you read any books or listened to any podcasts that changed your perspective?
25. What’s something you’re proud of that you never imagined achieving?
26. If you could go back and give your younger self advice, what would you say?
27. How do you handle stress or tough situations these days?
28. Have you started any self-care or mindfulness practices?
29. What’s one thing you’ve stopped caring about that used to bother you?
30. Have you had any “aha” moments lately that changed how you see life?

Career & Ambitions

31. How’s work going? Do you love what you do?
32. Have you changed career paths, or are you still on the same track?
33. What’s a recent work or business achievement you’re really proud of?
34. If money weren’t an issue, what would your dream job be?
35. Have you ever thought about starting your own business?
36. What’s the most exciting or challenging thing about your job right now?
37. Have you had any career “plot twists” that you didn’t expect?
38. Do you still have the same long-term goals, or have they changed?
39. If you could work anywhere in the world, where would it be?
40. What’s a career lesson you’ve learned the hard way?

Home & Daily Life

41. Have you made any changes to your home or living space recently?
42. What’s your go-to comfort meal these days?
43. Have you found any new favorite coffee shops, parks, or places to relax?
44. What’s your ideal way to unwind after a long day?
45. Are you more of a morning person or a night owl now?
46. Have you started any new home projects or renovations?
47. What’s your favorite way to spend a lazy Sunday?
48. Have you discovered any small habits that bring you unexpected joy?
49. Do you still live in the same place, or have you moved somewhere new?
50. If you could live anywhere for a year, where would it be?

Love, Relationships & Friendships

51. Are you dating anyone or in a relationship right now?
52. What’s one thing you’ve learned about love in the past year?
53. Have your views on relationships changed over time?
54. What’s your current love language?
55. What’s the best date you’ve ever been on?
56. Have you made any new friendships that surprised you?
57. What’s something you look for in a friend now that you didn’t before?
58. Do you still keep in touch with any mutual friends?
59. What’s one thing you appreciate more in friendships as you get older?
60. If we could take a trip together, where would we go?

Pop Culture & Entertainment

61. What’s the best movie or TV show you’ve watched recently?
62. What’s your current favorite song or music artist?
63. Have you read any books lately that you couldn’t put down?
64. What’s a social media trend that you secretly love (or hate)?
65. Have you attended any concerts, festivals, or live events?
66. Who would play you in a movie about your life?
67. If you could live in any fictional universe, which one would it be?
68. What’s one podcast you think I should listen to?
69. What’s a piece of pop culture nostalgia you wish would come back?
70. If you could meet any celebrity, who would it be and why?

Travel & Adventure

71. What’s been your favorite travel experience so far?
72. Have you ever considered moving to another country?
73. What’s the most spontaneous trip you’ve taken?
74. If you could road-trip anywhere right now, where would you go?
75. What’s one travel bucket list item you’re dying to check off?
76. Have you had any hilarious or wild travel mishaps?
77. Do you prefer adventure-packed vacations or relaxing getaways?
78. What’s one country or city you fell in love with?
79. Have you learned any new languages or cultural experiences?
80. If we could take a trip together, where should we go?

Final Thoughts

Reconnecting with an old friend is one of life’s greatest joys—it reminds us where we’ve been, how much we’ve grown, and why friendships are so precious. With these 100 unique questions, you’ll never run out of things to talk about, ensuring your next catch-up session is full of laughter, nostalgia, and deep connection.

Want more? Check out these Conversation Starter Cards on Amazon to keep the conversation going!

Now tell me which question are you most excited to ask your friend? Drop a comment below.