150 Conversation Starters for Grandparents

Discover Stories, Wisdom, and Laughter—One Question at a Time

Get to know your grandfather like never before with this thoughtfully designed box set, featuring 150 engaging questions that spark meaningful, fun, and heartfelt conversations between grandkids and their beloved grandpa. From lighthearted memories to deeper reflections, every card opens the door to connection across generations.

Inclusive and designed for grandkids of all ages, the questions are paired with a blank notebook for jotting down answers, memories, or even new questions of your own—turning shared moments into lasting keepsakes.

Highlights:

• 150 Thoughtful Prompts – A mix of silly, serious, and sentimental questions

• ✍️ Includes Blank Notebook – Record memories, insights, and favorite stories

• Beautifully Boxed Set – Makes a perfect gift for Father’s Day, birthdays, or “just because”

• Whimsical Illustrations – Fun, approachable design for all ages

Sample Prompts:

• What about being a grandfather has surprised you?

• Who was your childhood best friend and how did you meet?

• What traits do you see in me that remind you of yourself?

• Are you good at keeping secrets? Why or why not?

• What is your all-time favorite meal?

• Tell me how you first learned you were going to become a grandmother. How did you feel?

• What has surprised you most about the twenty-first century?

• What nicknames have you had throughout your life?

• Were you ever bullied? What did you do?

• What is something that never fails to cheer you up?

Whether you're sitting around the dinner table or taking a quiet walk together, Grandfather & Me makes it easy to share stories, spark laughter, and create memories that will be treasured forever.