The questions a kid asks their dad inevitably change—but even in adulthood, they shouldn't stop, according to East, a former NFL player who wrote The Courage to Commit and hosts a relationship and parenting podcast and YouTube channel with his wife, former Olympic gymnast Shawn Johnson East. He’s spent years thinking about how to say the things that matter before it's too late—something he did with his own dad. "You don't leave 'I love you' unsaid or 'I'm proud of you' unspoken," he says.
When East imagines the conversations he wants to have with his kids someday, this is one of the first that comes to mind—and it’s a telling one, coming from a man whose football career and later business ventures didn’t always unfold the way he imagined. He doesn’t want to hide that from his kids.
“What were you like when you were my age?”
Mark Papadas still remembers the conversation that transformed how he saw his father. He was in his late teens when he asked his dad about his own childhood and finally learned the losses and upheaval his father had grown up with. He never knew that his dad had a sister who’d died at 8, or that he’d been drafted into the Army at 18.
Even younger kids can benefit from this question, he says. A dad who says, “When I was 10, like you are now, here’s what I was up against, and here’s how I got through it” gives his child something to hold onto. “I’m sure that 10-year-old, when he’s 40, will remember that conversation,” Papadas says.
The photos matter to him less than the story behind them—and a wedding, he points out, holds a lot of story. In his own case, it meant blending Northern and Southern families with different expectations, priorities, and ideas about what a wedding should be. “How are we going to solve the money problems?” he remembers thinking. “How are we going to solve all these different visions?”
Retelling your family’s origin story lets you relive those memories, too. “Every time we retrieve it, we re-remember it,” Feiler says. Every retelling gives us a chance to revisit our lives from a new vantage point.
“Will you teach me something you love to do?”
“You don’t think of your parents before they were parents,” says Chip Leighton, author of Dad Can You Not?: A Dad's Guide to Being Less Cringey. To a kid, a dad has simply always existed, fully formed, with no history before they came along. “It would be an interesting thing to talk about that most kids wouldn’t think to ask.”
“What did you want to pass on from how you were raised—and what did you want to do differently?”
The question invites men to explain their parenting not as something that simply happened, but as a series of choices. What did your dad inherit from his own parents? What did he look at and decide, this stops with me?
Ask your dad this, Papadas says, and the answer will probably surprise you. Kids tend to assume they know the script: You’re proud of me for the A-plus, the trophy, the college acceptance. More often, what a father is proudest of is something else entirely.
“Are you OK, Dad?”
It’s a deceptively simple question, but sometimes a hard one to answer honestly. After Maguire’s son was born, he developed postpartum depression—something he’d been watching for in his wife but never imagined for himself. Then a friend asked how he was doing, and Maguire caught himself before he went on autopilot. Instead of “fine,” he said the true thing: “I’m not OK. I’m really not OK.” It changed the friendship for the better.
“If you were to give me your blessing, what would it be?”
Real means "blessing" not as a religious rite, but as a father's stamp of approval and wish for his child to live their best possible life. He'll always remember asking his own dad for one as an adult. At the time, his father had ALS and was paralyzed, but could speak with Real's mother holding the phone to his ear.
Real, who has spent decades helping men find words for the things they feel, has practical advice if you’re hoping to have a conversation like this. For one thing, don’t ambush your dad. Springing heavy, vulnerable questions on a parent out of nowhere rarely works—it's jarring, Real says. Preface the question by asking your dad if he feels up to having a serious conversation.
Then, have a little patience and grace. A lot of fathers, especially older ones, haven’t had much practice navigating these types of deep conversations. “Just because you’re asking your dad these questions doesn’t necessarily mean he’s going to open up and answer them in big, heartfelt ways,” Real says. “You may have to work for it.”
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