Going Deeper — In Conversations and Relationships

In a world of curated highlight reels and shallow small talk, real connection can feel like a lost art. In this episode, Chris and Patrick argue that deep, meaningful connection requires us to be a little messy, a little vulnerable, and a lot more intentional. They explore why we often feel most connected during our least polished moments — and how embracing emotional risk creates space for deeper conversations. Along the way, they share practical tips and mindsets to help you go deeper with the people in your life and start building bonds that actually matter.

What You’ll Learn:

• Why vulnerability is essential for true connection
• How shallow habits (like quick replies) are silently blocking intimacy
• Practical ways to deepen your everyday conversations
• How better listening and better questions can transform your relationships

Building deeper relationships starts with asking better questions. Here are five conversation starters designed to move beyond the surface and open the door to real connection.

1. "What’s something you’re excited about that most people wouldn’t expect?"

This helps reveal hidden passions and sparks surprising conversations.

2. "When was a time you felt truly seen by someone?"

A powerful way to invite emotional vulnerability and personal storytelling.

3. "What’s something that’s been on your mind lately, even if it feels small?"

Shows care for the little (but meaningful) thoughts we often keep hidden.

4. "What does feeling 'at home' mean to you?"

Gets at people's sense of belonging, safety, and authenticity.

5. "What’s something you wish people would ask you about more often?"

A direct, generous way to offer someone the chance to share what matters most to them.

Remember: Use these questions not as checklists, but as invitations. Go slow. Stay curious. Listen deeply.

Connection isn't found by staying safe — it's built by going deeper.