How to deepen your relationships with Tim Dean


Knowing how to get the most out of the people we meet, live with and love is so important to living a meaningful life.

But too often we struggle to communicate our true selves. We fail to connect deeply or have conversations that allow us to reveal our vulnerability and naturally relate to others. Instead, our chitchat can feel like it’s in a rut - mundane, dull and filled with innocuous nonsense about events, plans or the weather.

According to Tim Dean, the ability to be sociable and to relate to other people is a learned skill, and one that requires emotional intelligence - enhancing our ability to connect with those around us, and ourselves.

Tim Dean is a philosopher, science journalist and a faculty member of The School of Life - and in this rich conversation we discuss some big and bold topics, including:

  • How we can be better listeners to our friends and family;

  • How we can use social media mindfully;

  • How we can ask better questions so that we have richer conversations;

  • How we can handle family events where we have to interact with people that we don’t agree with very much.

Tim has so many wonderful tips for deepening our relationships and embracing difference, that I’ve found it’s enhanced the connection I have with my own friends, family and colleagues since trying his advice. I hope for you that it does the same.

This episode is a must listen for anybody looking to have richer conversations, more meaningful interactions, and to share your imperfections with others in a way that’s true, honest and joyful.



“When you really listen to somebody you signal to them that you care.”


Asking Better Questions Exercise:

There are two different types of questions: surface questions and deeper questions.

We often spend a good portion of our daily interactions asking these ‘surface’ questions. Surface questions are generally event based questions - the wheres, whats, whens and hows of life. These can include:

  • What have you been up to? What did you do next? Where did you study? How did you go?

While these questions undeniably have an important role in day-to-day life, they also limit our ability to connect with others deeply when we fail to ask them more meaningful or poignant questions.

Now, consider these deeper questions:

  • How do you feel now that that’s happened? Are you concerned about the implications? What are your fears if that happens?

When we truly listen to others and ask them deeper questions, we create an opportunity to connect. We show them that we truly care. That we respect them. That we can be trusted. It feels so good to be deeply listened to by another person. Offering somebody our true attention is a gift.

Try this at home:

  • Sit down with a friend and share the questions above.

  • Set a timer for two minutes. Your goal is to have a conversation where one of you asks the other surface questions about a single topic (for instance: your weekend plans). Do not stray into the deeper questions - they’re for later. Think of as many surface questions as you can in the two minutes.

  • Swap roles.

  • Setting your timer again, revisit the same topic but ask deeper questions this time. It will be harder, and you’ll probably have to think before asking questions. That’s okay, take your time. Challenge yourself to think of as many deep questions you can in the two minutes.

  • Swap roles again.

  • Reflect on how the two conversations went, how often you rely on surface questions in daily life, and how you can introduce deeper questions in your daily interactions.


“There’s a global listening deficit. Because we are so motivated to talk and express our views and feelings we don’t really give ourselves and others the chance to go deeper. We all want to be listened to more than we have the capacity to listen to others. Learning how to listen well is an incredibly powerful way to build relationships.”


Via The School of Life: We often think that the best way to have friends is to be deeply impressive and accomplished. In fact, the route to true friendship always flows through vulnerability.


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Kayla Robertson