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12 Questions to Ask Your Dad Before He’s Gone

If you have the opportunity to connect, don't let it pass.

There are plenty of reasons why it can be difficult for men to connect with their fathers. Maybe your relationship isn’t exactly a model of emotions and vulnerability. Maybe you’re both too busy to sit down and have a meaningful chat. Maybe you don’t know how to even broach such a topic. When he’s gone, though, all of those reasons will turn into regrets and thoughts of “What if…?” when it comes to what may have been. The point? Don’t waste time, succumb to pride, or entertain doubt when considering what you’d like to know about your father. 

For those who still have the ability, the chance to connect with one’s father is nothing short of a treasure. “For my clients, this realization often comes in the form of a wake-up call,” says Michael Ceely, a marriage and family therapist who is an expert in family dynamics and primarily works with men and athletes. “Maybe their father has received a terminal diagnosis of cancer and suddenly has six months to live. Or maybe there’s a horrible accident. Some clients even seek to confront their fathers about abuse, or unfortunate things from their own childhoods. It’s a conversation that many men want to have, but don’t know how.” 

Connecting with your father as an adult adds far more nuance to the relationship, too. It’s much different than getting a lecture as a punk teenager home past curfew. Dad’s wisdom is likely poignant, his life experience is well-documented, and his words are cherishable. Ideally, a conversation with Dad is a conversation with a father, a friend, and a mentor, and a man all wrapped up in one. And in order to make the most of such an opportunity, you have to know where to start. 

“Men often avoid asking deep questions until it’s too late,” says Ceely. “But it doesn’t have to be that way.” So what are some questions to ask? To help get things started, Ceely provided a dozen questions men should ask their father before it’s too late.

1. What are you most proud of in your life?

Chances are, he’s going to say you. Right? “The default answer will probably be family,” admits Ceely. “But, that doesn’t mean it isn’t true.” On the other hand, Ceely says he might surprise you by saying something else — something he’s personally proud of. Either way, this is one of those great, feel-good questions that can really get him to open up. A question like this can strengthen your father/son relationship through one of the most important qualities it can have – honesty. “Maybe it’s something he’s never shared with anyone before,” says Ceely. “Or maybe he’s only shared it with a few close friends, or your mom. It’s a way to bring yourselves to a new level of honesty without prodding.”

2. Why did you choose your career?

“As sons, our fathers’ careers have huge influences on our own career choices,” says Ceely. It’s good to understand: Was your dad’s career his passion? Or did he make a practical choice to provide a stable income for his family? “Knowing why your dad chose his career can give you very valuable insight into your own career path, as well,” he adds. The information is important to know to shade in more about who your father is. But if you’re at a career crossroads, Dad’s wisdom is even more sacred. “What he says might not make you change your career overnight, but it might make you think about things and re-examine exactly why you’re doing your current job.” 

3. Who was the most influential person in your life?

The answers here are boundless. It could be his dad. It could be John F. Kennedy. It could be John Belushi. Whoever it is, that person will give you insight into what your dad values, even if he doesn’t come right out and say it. “Influential people in our lives typically have characteristics we want to develop,” Ceely explains. “This question will allow you to gain insight into the principles that are most important to your dad.” Ceely says clients have cited teachers, coaches, and even former employers as candidates for the question — different people, for similar reasons. “The answer to this question will be someone who came into your dad’s life and showed him something important about himself. That’s a great thing to know.”

4. What do you admire most about your own father? 

Depending on your father’s relationship with his own father, this could be a point of pride or a sore spot. But either truth can serve to bring you two closer. Your father’s relationship with his own father may have been wonderful, or it may have been challenging, notes Ceely, so you may not want to force it. But usually, he says, even if their relationship was rocky, your dad will be able to describe at least one thing. Maybe he was tough, but a good provider. Maybe he was a jerk, but he worked hard his whole life. Even if he doesn’t have an answer, now you’ve got a perfect excuse to tell your dad what you admire most about him.

5. What’s your biggest life lesson?

This question, per Ceely, can elicit a profoundly valuable response not just for you, but for your own children as well. Of the many, many lessons your dad has learned over the decades of his life, he’s giving you the biggest takeaway. But, dads are full of life lessons, right? How do you get him to choose just one? If he’s struggling to answer, then break it down into life domains. You could ask him about his biggest life lesson related to marriage. Or raising kids. Or finances. When you were a teenager, Dad’s lessons and lectures hit differently. Now that you’re an adult, those same speeches are sacred parts of his legacy.

6. Is there anything you regret not doing in your life? 

“I asked my dad this question,” confesses Ceely. “He told me about a career opportunity that he had earlier in his life, and how he turned it down. He said he’ll always wonder what would’ve happened if he would’ve taken that job.” It also may be great to flip the question to ask if there’s anything he does regret doing. This inquiry is more about reflection and less about gossip. “You don’t want dirt on your dad,” says Ceely. “You want to respect the vulnerability inherent with this question as he admits what he never got to do. His answers might be surprising, and could definitely give you ideas about what you can add to your own bucket list.”

7. How would your father describe you? 

This can be a really sensitive topic, warns Ceely. But it gives you a chance to put yourself in your dad’s shoes. If you have a son, and your son asked you that question, what would you say? “When you listen to your dad’s answer, think about that,” says Ceely. “Make no mistake, this is a high-risk/high-reward exploration into your dad’s mind — especially if his relationship with his own father is less-than-stellar. But a cautious approach can yield beautifully honest results. Consider what you know about his relationship with his father first. “You could even want to reframe it as, ‘What would your father say is the best thing about you?’ if you think that might elicit a more honest answer that skews positive.”

8. What mistake taught you most about life? 

“Offer your own answer first,” suggests Ceely. “This is called ‘disclosure reciprocity’. If you warm things up, you’ll be more likely to get an honest answer, or at least give him an idea of what kind of answer you’re after.” This is a chance for you and your dad to share something rare and precious and to be vulnerable with one another. “If you learn that your dad has made similar mistakes to ones you’ve made, it becomes a great opportunity for growth,” says Ceely. “It’s cliche, but everyone really does make mistakes. Even dads.”

9. What world event had the most impact on you?

This is a great question to get a sense of generations.  “Most people’s minds go to negative, catastrophic events when they hear a question like this, so hearing your dad’s answer will give you a sense of historical perspective, likely from before you were born.” Misery loves company, and if both of your answers happen to skew toward tragedy a bond can grow. “Commiserating over something of this magnitude is a chance for a real conversation,” adds Ceely. “And world events affect us all.” 

10. What do you enjoy most about being a father?

“If I’m asking my dad that question,” says Ceely, “I’m guaranteed to reframe my perspective as a father too. It’s such a good, positive question, with so many possible answers.” Questions like this one give Dad a chance to reminisce with stars in his eyes, rather than tears, as he looks back on his accomplishments as a father. “It’s very easy for dads to be self-critical,” says Ceely. “So a question like this just allows him to focus on joy – simple joy – and what he loves about being a dad.”

11. What was the hardest moment for you as a father? 

“This is a gut check moment for dad,” says Ceely. “Remember, though, these questions are about conversation, not interrogation. Ultimately, hearing his answers to tough questions like this one can help you become a better parent.” Maybe it was the time you broke your arm learning to ride a bike. Maybe it was your first broken heart. Maybe it had nothing to do with you and involved a sibling or loved one. Whatever the moment, there’s a reason it happened. “This question could very easily turn into life-changing advice,” adds Ceely. “It’s very easy for dads to start preaching when they self-reflect.”

12. What’s one story I don’t know about you? 

As iconic, legendary, and seemingly mythical as your dad may be, remember: he’s still a human being. “This is a great question because it gives your dad a chance to humanize himself in your relationship,” explains Ceely. Most of us naturally idealize our fathers. As we get older, and as they feel more comfortable sharing stories about their lives, we learn that they’re human. They have faults. They’ve done crazy things in high school or college. Things that you’d never believe as a kid. By sharing an outlandish tale or two, Dad is giving you the nod by letting you know that, while you’re old enough now to appreciate his shenanigans, you’ll always still be his little kid.