JournalConversation3 min read

40 Conversation Starters That Get Grandparents Talking

"How are you?" gets "Fine." These questions get stories. Use them at the dinner table, on a visit or during a weekly phone call.
A grandfather telling a story to his teenage granddaughter while they look at old photos

Ask a grandparent "How are you?" and you'll usually hear "Fine." Ask "What did you do on summer vacation when you were ten?" and you might get twenty minutes of stories nobody in the family has ever heard.

Talking about the past, sometimes called reminiscence, is one of the easiest and most enjoyable activities for older adults. Long-term memories are often the strongest, and sharing them lets grandparents be the expert in the room. Here are 40 questions to get started.

Growing up

  1. What did the house you grew up in look like?
  2. What chores did you have as a kid?
  3. What was your favorite toy or game?
  4. Who read you stories, and which one did you love?
  5. What did you get in trouble for?
  6. What was your nickname, and where did it come from?
  7. What did you want to be when you grew up?
  8. What was your favorite candy, and how much did it cost?

School and work

  1. How did you get to school every morning?
  2. Who was your favorite teacher, and why?
  3. What was your very first job?
  4. What did you buy with your first paycheck?
  5. Who was the best boss you ever had?
  6. What job taught you the most?

Music, movies and fun

  1. What song takes you right back to being young?
  2. What was the first record you bought?
  3. Did you go dancing? Where?
  4. What was the first movie you saw in a theater?
  5. Which TV show did your family watch together?
  6. What did you do on a rainy Saturday?

Family and love

  1. How did you meet your husband or wife?
  2. What was your wedding day like?
  3. What is a family saying everyone repeats?
  4. Who was the best cook in your family, and what was their famous dish?
  5. Which family trip do you remember best?
  6. What do you hope our family never forgets?

Holidays and traditions

  1. Where did your family gather for Thanksgiving?
  2. What was your best Halloween costume?
  3. Where did you watch Fourth of July fireworks?
  4. What gift do you still remember?
  5. How were birthdays celebrated when you were young?

Wisdom and fun

  1. What is the best advice you ever got?
  2. What mistake taught you the most?
  3. What invention changed your life the most?
  4. What do you miss most about the old days?
  5. What is something you're proud of?
  6. If you could visit any year again, which would it be?
  7. What makes a good friend?
  8. What would you tell your 20-year-old self?
  9. What makes you laugh every time?

Tips for great conversations

  • Pick two or three questions, not twenty. Let one answer turn into a story.
  • Follow up. "What happened next?" and "What did it smell like?" bring memories to life.
  • Bring props. Old photos, a favorite song or a family recipe can unlock a lot.
  • Let kids ask. Grandchildren asking questions is a gift for both sides.
  • Write it down. Keep the best stories in a notebook or a keepsake journal. They become family treasures.
  • Skip what hurts. If a topic brings sadness, gently move to another one.

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