20 thoughtful questions to ask your dad

One day, it will be too late to ask our dads questions. The best time to hear his stories and preserve his wisdom is right now.

It's sobering to think that our dad won’t always be around to share his stories, give advice or shoot the breeze over a cup of tea. Many of us take our father figures’ presence for granted. And yet, whether they're biological dads, adoptive fathers, stepfathers or grandfathers, these men play a huge role in shaping us. 

This realisation inspired us to compile 20 thoughtful questions to ask your dad. Whether you're looking to transform superficial conversations into meaningful moments, or simply explore new ways to celebrate his life, these important questions uncover chapters in your dad's history and preserve them as keepsakes.

The power of asking questions

Initiating deep conversations with your dad may feel uncomfortable at first. After all, many of us struggle to open up and that's completely normal. 

If your relationship with your father is complex or a little distant, or perhaps the exercise just feels awkward, structuring conversations around predefined questions is a useful approach. Skip questions that make either of you uncomfortable and focus initially on sharing happy memories. This should relax you both, build trust and encourage openness over time. 

Whether you choose to meet in person, on video chat or even over the phone, we suggest starting these conversations with some icebreaker questions:

Lighthearted questions to ask Dad

• What do you most like doing in your spare time?

• What's your favourite film or book and why?

• What three items would you take with you to a desert island?

• If you could learn any new skill in one day, what would it be?

Uncovering the hidden Dad lore from photos

Now the conversation’s flowing, start flipping through his old pictures – you might uncover a treasure trove of unheard stories that piece together his version of “Dad Lore” – the TikTok trend where people share stories about their fathers' lives before they met their mothers. Tales are frequently filled with adventure, drama and intrigue, leaving children amazed at the untold chapters of their dad’s past. 

When looking through his travel photos, concert snaps and football team portraits, ask him: "What's the story behind this photo?"

Photos are such a powerful tool when used this way – expect this question to prompt stories about travels, long-lost friends and youthful adventures. You can also explore memories of his undocumented younger years by asking more general, nostalgic questions about Dad’s childhood. 

Nostalgic questions to ask your father

• What hobbies did you enjoy as a teenager? 

• What are your best memories of the town you grew up in?

• Who were your best childhood friends, and what did you get up to together?

• What was the best holiday you went on before I was born?

Understanding his fatherhood journey

Delving a little deeper into your dad's experience of fatherhood can help you understand the joy and growth he experienced as a parent. Try exploring these perspective-shifting questions:

Questions about fatherhood to ask your dad 

• What was going through your mind on the day I was born?

• What was your favourite thing about raising me?

• How has becoming a dad made you a better person? 

• What advice would you give someone who is about to become a parent for the first time?

Reflecting on Dad’s greatest life lessons

We've all heard those classic, often exaggerated stories from our dad's youth: "When I was your age, I had to walk 10 miles to school, uphill both ways!" 

While these tall tales can elicit eyerolls, they can also be a springboard for deeper conversations about your father's important life lessons. 

Instead of dismissing these anecdotes, try turning the tables and ask him: "When you were my age, what were you struggling with, and how did you overcome it?"

This unconventional question invites him to reflect on his fears, his mistakes and the resilience he's developed. To dig deeper into his well of fatherly wisdom, try these additional topics: 

Life lesson questions to ask Dad 

• What's the best advice you received growing up?

• If you could go back in time and change one thing about your life, what would it be?

• What was your proudest moment in your career, and what did the experience teach you?

Meaningful questions to ask Dad about his legacy

It's not often that we are asked to reflect on life's bigger purpose and the kind of legacy we hope to leave. Creating space to hear about your dad's deeply held beliefs and hopes for future generations could ignite connection on a profound level.

Deep and meaningful questions to ask Dad  

• What do you believe gives life meaning and purpose?

• If you could pass down one piece of advice for future generations, what would it be?

• What impact do you hope your life will have on others?

Preserving the memories that matter with Popsa

These deep conversations with your dad are invaluable and should be preserved as cherished memories to share with future generations. 

Consider documenting your “Questions to ask Dad” project in various formats. You could keep notes and jot down his memories in a journal. Or you can capture the entire conversation, using voice recording tools like Otter AI to instantly convert your conversation into text.

To make the experience of sharing memories more tangible and enriching, create a Photo Book of the pictures you discussed and the stories behind them. The Popsa app makes it easy to design your Photo Book and add captivating captions that highlight your dad's unique philosophy on life.

Share your memory book projects and Father’s Day photo gifts with @Popsa on Instagram. We'd love to see how you transform meaningful conversations into treasured family keepsakes.