We've all had the experience: you're on the phone with a parent or grandparent, and the conversation follows the same well-worn path. How are you? Fine. How's work? Fine. How are the kids? Good. Fifteen minutes later, you hang up having said nothing real.
It's not that your family doesn't have stories to tell. It's that we rarely ask the questions that invite them out. Here are five that work remarkably well.
1. "What were you like at my age?"
This one works because it's personal without being intrusive. It asks your parent to remember a specific time in their life — not in the abstract, but in comparison to where you are now. You'll hear about apartments they lived in, friends they had, mistakes they made, and dreams they were chasing. And you'll start seeing them as a person, not just a parent.
2. "What's a moment you think about more often than people would expect?"
This question skips past the highlight reel. It doesn't ask for the proudest moment or the happiest day. It asks for the ones that stuck — and those are often the most interesting. A conversation with a stranger on a train. A morning when the light looked a certain way. The time they almost made a completely different choice.
3. "What did your parents get wrong? What did they get right?"
This is a generous question because it gives permission to be honest. Most people have complicated feelings about how they were raised, and they rarely get asked about it directly. The answers often reveal patterns — things your parent consciously did differently, or things they repeated without realizing it.
4. "What's something you know now that you wish you'd known at 25?"
People love this question because it lets them be wise without being preachy. It's an invitation to reflect, not lecture. And the answers are almost always surprising. It's rarely about money or career. It's usually about worry, or kindness, or the way time works differently than you expect.
5. "Is there a story from your life you've never told me?"
This is the big one. Direct, a little vulnerable, and impossible to answer with "fine." Sometimes the answer is no — and that's okay. But sometimes a door opens that's been closed for decades. A story from before you were born. A chapter they never thought anyone would want to hear.
The trick: just listen
The best follow-up to any of these questions isn't another question — it's silence. Give your parent space to think, to remember, to find the thread. The stories that matter most often start slowly. Let them unfold.
And if you want to make sure you don't lose what they share, consider recording the conversation. Not with a camera in their face — just a phone call. Their voice, their words, preserved exactly as they said them.