100 Conversation Starters for Siblings

Siblings can be our best friends and sometimes our biggest mysteries. Finding the right topics to talk about can help bridge the gap and make your relationship stronger.

Whether you’re reuniting after a time apart or just looking to spark more meaningful conversations, the right approach can make all the difference.

In this piece, I’ll walk you through some practical conversation starters to help you connect better with your siblings. These suggestions range from fun and light-hearted to deep and thoughtful, ensuring there’s something for every moment.

Childhood Memories

1. Remember when we built that fort in the backyard?
2. What’s your favorite childhood memory?
3. Do you recall our funniest family vacation?
4. What cartoons did we always watch together?
5. Did you have a favorite toy growing up?
6. What was your favorite game we played?
7. Remember our first pet?
8. Do you remember any pranks we pulled?
9. What was your best birthday?
10. Did you ever get in trouble but didn’t admit it?
11. What was your favorite holiday as a kid?
12. Who was the best cook in the family?
13. What was the scariest movie we watched as kids?
14. How did we spend our weekends?
15. Do you remember our secret handshake?
16. What’s a funny story you remember about me?
17. Who was your best friend during our school years?
18. What’s the silliest fight we ever had?
19. What was the most memorable Christmas gift you got?
20. Did we have a favorite bedtime story?

Family Traditions

1. What’s your favorite family tradition?
2. Do you remember how we celebrated holidays?
3. Which family event do you look forward to every year?
4. What special meals did we have during the holidays?
5. How did we usually spend Thanksgiving?
6. What quirky family traditions do you miss the most?
7. How did we celebrate our parents’ anniversaries?
8. What traditions do you want to keep alive?
9. Did we have any unique holiday rituals?
10. What’s one tradition you would like to start?
11. What did we do every New Year’s Eve?
12. How did we celebrate birthdays?
13. Did we have any traditions around school events?
14. What was our Saturday morning routine like?
15. How did we typically celebrate achievements?
16. What did we do on the first day of school?
17. What’s your favorite family holiday photo?
18. How did we decorate the house for the holidays?
19. What’s a tradition you didn’t like but appreciate now?
20. How did we spend lazy Sundays?

Life Updates

1. How’s work going these days?
2. Have you picked up any new hobbies lately?
3. How’s the family doing?
4. What shows or movies have you been watching?
5. Any upcoming trips you’re excited about?
6. How’s your health been lately?
7. What’s the highlight of your week so far?
8. How’s your best friend from high school doing?
9. Have you read any good books recently?
10. Do you have any new favorite restaurants?
11. Are you working on any personal projects?
12. How’s your significant other?
13. Any exciting plans for the weekend?
14. Have you learned anything new or interesting?
15. How are your neighbors?
16. How’s your garden (or plants) doing?
17. Did you attend any fun events recently?
18. How’s your new job/house/car?
19. Do you have any upcoming celebrations?
20. How’s your pet doing?

Hobbies and Interests

1. Have you tried any new recipes lately?
2. What’s your current favorite song or album?
3. Any new shows or movies you recommend?
4. Have you read any good books recently?
5. What’s your current favorite hobby?
6. Are you learning any new skills?
7. Have you taken up any new sports?
8. What podcasts are you listening to?
9. Have you visited any cool places recently?
10. What’s your favorite way to relax?
11. Do you play any video games?
12. Have you been to any art exhibits lately?
13. Do you like any new board games?
14. Are you following any interesting YouTube channels?
15. What’s your favorite thing to do on weekends?
16. Have you taken any interesting classes?
17. What’s your go-to comfort food?
18. Do you have any travel destinations in mind?
19. What crafts or DIY projects have you done?
20. What’s your favorite outdoor activity?

Future Plans

1. What’s your next big goal?
2. Do you have any upcoming trips planned?
3. Are you planning any big changes this year?
4. What’s your dream job?
5. Where do you see yourself in five years?
6. Any plans for further studies or courses?
7. Are you planning to buy a house/car soon?
8. What’s one thing you hope to achieve next year?
9. Do you plan to start any new hobbies?
10. Are you planning any renovations to your home?
11. What’s on your bucket list?
12. Do you have any financial goals?
13. Are you planning any family events?
14. What’s your fitness goal?
15. Any upcoming milestones you’re excited about?
16. Do you plan to volunteer or give back to the community?
17. Are you considering adopting a pet?
18. What vacation spots are on your mind?
19. Any plans for career advancement?
20. What’s one skill you plan to master?