When I first visited Paddington Bear’s fictional home at 32 Windsor Gardens, I wasn’t sure what to ask him. After all, this is a bear who’s lived in London for decades, survived countless mishaps, and somehow always managed to bring out the best in people. What struck me most wasn’t his marmalade sandwiches or his red hat — it was his quiet wisdom, the kind that comes from living with kindness as your compass.

If you ever get the chance to talk to Paddington, here are the questions I’d recommend asking — and why they matter.

1. “What made you decide to leave Peru and come to London?”

Paddington’s journey from darkest Peru to Paddington Station is the start of his entire story. By asking him this, you’re not just tapping into the plot of his origin — you’re inviting him to reflect on courage, curiosity, and trust. He left everything familiar behind, guided only by the hope that strangers might be kind. It’s a beautiful and brave decision that says a lot about who he is.

2. “How did you feel when the Browns first took you in?”

This question gets to the heart of Paddington’s emotional world. He went from being alone and unsure to finding a family that, while not always understanding him, always tried. Asking him about those early days opens up a conversation about belonging, patience, and the small ways people show they care — even when things go wrong.

3. “What’s the most important lesson you’ve learned in London?”

Paddington has had countless adventures — and misadventures — in his time here. But beneath the surface of each story is a gentle moral, often about kindness, honesty, or the importance of trying your best. Asking him this gives you a glimpse into how he makes sense of the world, even when it doesn’t make much sense at all.

4. “How do you stay so polite even when people aren’t kind to you?”

This is one of my favorite questions to ask Paddington. In a world that often feels impatient and unkind, his unwavering politeness is a kind of resistance. He never retaliates, never gives up on people — and that’s not naivety. That’s strength. Talking to him about this might just remind you how powerful a simple “please” or “thank you” can be.

5. “What’s your favorite thing about London?”

London isn’t just a backdrop for Paddington’s life — it’s a character in its own right. From the station where he was found to the museums he loves to visit, Paddington’s relationship with the city is deep. Ask him this, and you’ll hear stories that reflect his curiosity and appreciation for the small joys in life.

6. “Do you ever miss Peru?”

It’s easy to forget that Paddington came from another continent, another culture. Asking him if he misses home is a respectful way to acknowledge his roots and his identity. His answer might surprise you — it’s likely filled with both longing and gratitude, a balance many of us understand.

7. “What’s the funniest misunderstanding you’ve ever had?”

Paddington is famous for his misunderstandings — they’re the source of much of the humor in his stories. But these mishaps also reveal something deeper: how language and culture shape our experiences. Asking him this opens up a lighthearted but meaningful conversation about how we connect with others, even when we don’t always get things right.

8. “How do you handle it when things go wrong?”

Because things do go wrong for Paddington — often in spectacular ways. Yet he rarely gets discouraged. Talking to him about how he deals with setbacks might offer you a new perspective on resilience. He doesn’t dwell on mistakes; he moves forward with optimism and a willingness to learn.

9. “What does ‘home’ mean to you?”

Paddington’s answer to this might surprise you. After all, he started out as a stranger in a strange land. But over time, home became more about the people around him than the place itself. Asking him this question could lead to a deeply touching conversation about love, memory, and the quiet comfort of belonging.

10. “What would you tell a new bear arriving in London today?”

This is a question that invites Paddington to reflect on everything he’s learned. It’s also a way to hear him pass on his wisdom in a way that feels personal and generous. His advice would likely be simple — and all the more powerful for it.

Talking to Paddington Bear isn’t just a whimsical idea. It’s a chance to connect with someone whose kindness cuts through the noise. If you’re curious about his answers, there’s a place where you can ask him yourself.

Learn about & chat with Paddington Bear