Andrew East’s kids are at the age when the questions never stop. His 2-year-old points at the world and asks, “Daddy, what’s that?” His 4-year-old wants to know why—why the family’s chickens get one particular type of food, why a fire needs kindling before logs, why the trail goes up before it comes back down. And his 6-year-old has started reaching for the bigger ones: “Where’s Papa now?” she asks about her late grandfather. “What was he like?”

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.

We asked East and five other thoughtful dads what they hope their kids will someday ask them—and what questions they’d like to ask their own dads.

“Dad, what scars do you have—and what did you learn from them?”

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. 

“There’s so much power in telling the truth of the things that have gone well and the things that have gone poorly,” he says. The lesson he hopes his kids take away isn’t that life goes according to plan. It’s what to do when it doesn’t. “It doesn’t mean you stop going,” he says. “It means you learn, you redirect, and you keep pressing forward.” A scar, after all, is proof that something healed.

“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.

“It gave me a whole new version of him,” says Papadas, who founded the youth character-building program I Am for Kids. Decades later, the conversation has stayed with him. 

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.

“What was it like getting married? What were the best and worst parts?”

Author Bruce Feiler wishes more kids would ask their parents about their engagement and wedding because it opens the door to much more than a love story. Weddings are where families intertwine, traditions get negotiated, conflicts surface, and new chapters begin. Feiler felt that when he got married. Sitting at the edge of the dance floor holding his wife's hand, he says, “I time traveled”—first imagining himself as a child looking at his parents' wedding photos, then picturing his own future children someday looking back at his. The irony that still gets him: his daughters are now 21, "and they've never looked at our wedding photos." 

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?”

That tension is exactly why he doesn't want parents to tell the polished version of their family history. Children benefit most from true stories that include both triumphs and setbacks, he says. 

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?”

Kevin Maguire, founder of the popular newsletter and community The New Fatherhood, has offered more than once to teach his kids to DJ—a craft he’s loved since working at a record store. The response has been underwhelming. That’s the cruel comedy of parenting: sometimes, whatever you do is the least-cool thing imaginable. (Even rock stars, he points out, come home to kids who’d rather not see the concert footage.) Still, he hopes one of them takes him up on it someday. A kid who wants to learn what their dad loves is really asking to know him, he says—not as the guy who packs lunches, but as a person with a whole life and a passion that predates them. 

“What was it like when you became a dad?”

“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?

Real especially likes this follow-up: “And by the way, Dad—how do you think you did? Did you do it differently, or did you repeat more than you wished you had?” The question asks for honesty rather than perfection. It gives fathers permission to talk about the gap between their intentions and reality—something many rarely discuss.

“What makes you proud of 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.

“They might have gotten a C in math,” Papadas says, “but you saw them working, and they were putting their best effort into it, and they weren’t giving up.” That’s the thing a dad carries, he says. “I’m proud of your resilience. I’m proud of your work ethic.” It’s a small question that teaches a child what their dad actually values—and, often, gives them permission to value it in themselves.

“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.

That's what makes this question so powerful coming from a kid. Maguire has felt it with his own children: his 7-year-old can sense a heavy day and will come over and ask, “Are you OK today? Have you had a good day today?” It isn't about making a child responsible for a grown-up's feelings—it's the plain comfort of being noticed. Young kids take a lot of care and energy, Maguire says, but “they give so much back.”

“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.

"May nothing in my life, and nothing in my history, stop you in any way from realizing your fullest potential," he told his son. Real has carried those words ever since. 

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.

Make it clear you're asking as an adult, not as a child. A script like this can be helpful to follow, says Real: “I was a child, and I’m glad you protected me. I’m an adult now—you don’t need to protect me anymore. I want to know who you really are.” And when in doubt, “Frame it as a favor to you,” Real says. “‘I want to be closer to you. I want to understand you better.’”

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.”