Awkward Family

A guide to awkward holiday conversations


Family dinners are a time to bring the generations together – for better or worse. For many of us, memories are made sitting around the dinner table telling family stories that connect us to each other.

However, getting everyone to open up and talk is often easier said than done. So before nosy Aunt Jane asks about Uncle Joe’s colonoscopy or Grandma asks if Abby is ever going to get married, here are a few conversation starters to help you bridge the generational gap and have some meaningful – and entertaining! – conversations around your holiday dinner table:

  • What was the best gift you received as a child?
  • Who is one of your heroes and why do they inspire you?
  • What was the first thing you ever saved money for?
  • What are the foods you remember from childhood?
  • What is the craziest thing you ever did when you were a kid?

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