100 Questions to Ask Your Cousins

Catching up with cousins can sometimes feel like rekindling old friendships—you’re tied by blood but often apart by life’s twists and turns.

I’ve put together a list of questions that’ll help bridge gaps, spark laughter, and deepen bonds.

Whether you’re chatting at a big family reunion or just texting to keep the connection alive, these prompts can make every interaction count.

Icebreaker Questions

1. What’s the most exciting thing that’s happened to you lately?
2. If you could have any superpower, what would it be?
3. What’s your favorite way to spend a weekend?
4. What’s the best meal you’ve had recently?
5. If you could live anywhere in the world, where would it be?
6. What’s one thing you’ve always wanted to learn?
7. What’s your go-to comfort food?
8. If you could swap lives with anyone for a day, who would it be?
9. What’s the last movie or show you watched?
10. If you could only listen to one song for the rest of your life, what would it be?
11. What’s your favorite holiday and why?
12. What’s the most adventurous thing you’ve ever done?
13. If you could have dinner with any historical figure, who would it be?
14. What’s your favorite way to unwind after a long day?
15. What’s the coolest place you’ve ever visited?
16. What’s something you’re really passionate about right now?
17. If you could master any skill instantly, what would it be?
18. What’s the best piece of advice you’ve ever received?
19. What’s one thing that always makes you smile?
20. If you had to describe yourself in three words, what would they be?

Life Updates and Future Plans

1. How’s work or school going for you these days?
2. What have been some major highlights for you this past year?
3. Any big plans coming up that you’re excited about?
4. How have you changed in the last five years?
5. What are you most proud of accomplishing recently?
6. Have you moved to a new place or thinking about it?
7. Any relationship updates you’d like to share?
8. What are some goals you’re setting for the next year?
9. What’s the biggest challenge you’ve faced recently?
10. How have your interests or hobbies changed over time?
11. Are you planning any trips or vacations soon?
12. Have you started any new projects or ventures?
13. Is there a new skill you’re trying to master?
14. What changes are you hoping to make in the near future?
15. What’s the most important thing on your mind these days?

Childhood Memories

1. What’s your earliest memory of us hanging out together?
2. What was your favorite game to play when we were kids?
3. Do you remember any family traditions we used to have?
4. What’s the funniest thing that happened when we were little?
5. Do you remember any silly fights or misunderstandings we had?
6. Do you remember the first time we got in trouble together?
7. What’s a memory that always makes you smile?
8. Do you remember any secret clubs or games we made up?
9. Do you remember the first movie we watched together?
10. Do you remember any silly pranks we pulled on each other?

Family Connections and Traditions

1. What’s our family’s most unique tradition?
2. Do you remember how we celebrated holidays when we were younger?
3. Who in the family do you think has taught you the most?
4. What’s a family story you love to hear over and over?
5. How do you think our family is different from others?
6. What do you value most about our family culture?
7. What family recipe can you not live without?
8. What’s the best family reunion we’ve had?
9. What are your favorite family photos or videos?
10. What aspect of our family culture are you most proud of?

Dreams and Aspirations

1. What’s one dream you’ve always had?
2. If you could start any business, what would it be?
3. What’s the biggest risk you want to take?
4. What’s the next big step you’re planning towards your dream?
5. What’s a recent achievement that you feel is a step toward your aspirations?
6. What’s one thing you hope to learn that could change your future?
7. Are there any roles or titles you aspire to achieve?
8. What’s one adventure you must have in your lifetime?
9. How do you stay positive when things don’t go as planned?
10. What’s a dream you’ve had since childhood?

Hobbies and Interests

1. Have you picked up any new hobbies recently?
2. Do you have any creative outlets or talents?
3. How do you usually spend your free time?
4. Are there any activities or sports you love to play?
5. What’s the last book you read or movie you watched that you really enjoyed?
6. What kind of music are you into these days?
7. Do you have any collections or special interests?
8. Do you like to cook or bake? What’s your favorite thing to make?
9. Are you into any video games or board games?
10. What’s your favorite way to relax after a busy day?
11. Do you enjoy any outdoor activities like hiking or camping?
12. What’s a new skill or craft you’ve been learning?
13. What’s your favorite type of art or creative expression?
14. Do you have any pets? Tell me about them!
15. Do you enjoy traveling? What’s your favorite place you’ve been to?

Shared Experiences and Inside Jokes

1. Do you remember that time we got lost together?
2. What’s the funniest thing that’s ever happened to us?
3. Do you remember our secret handshake or code words?
4. What’s a silly nickname we used to call each other?
5. Do you remember that one family trip where everything went wrong?
6. What’s a prank we pulled on someone together?
7. Do you remember that time we laughed so hard we couldn’t stop?
8. What’s an inside joke that only we would understand?
9. Do you remember the first time we did something adventurous together?
10. What’s the most embarrassing thing that happened to us?
11. Do you remember that one game we used to play all the time?
12. What’s the best day we’ve ever spent together?
13. Do you remember that one time we got in trouble but it was worth it?
14. What’s a funny misunderstanding we had?
15. Do you remember the time we stayed up all night talking?
16. What’s the most random thing we’ve ever done together?
17. Do you remember that one inside joke we still laugh about?
18. What’s a memory that always makes you smile when you think of us?
19. Do you remember that time we did something really spontaneous?
20. What’s a tradition we’ve created between just the two of us?