Friendship: Why is it Hard to Make Friends as an Enneagram 5?

Fives pride ourselves on independence, but friendship requires letting people in.

In this honest and deeply personal episode, we explore what friendship means to us as Fives—and why it’s so complicated. We share stories of how our personalities have made friendship harder, how we’ve grown to value it more, and the unexpected ways we’re learning to show up more authentically and connect more deeply.

From childhood loneliness to cold plunges and community-building, we dive into the vulnerabilities, narratives, and patterns that shape our relationships, and what it looks like to break through them.

IN THIS EPISODE:

🔹 What Is Friendship? — Redefining friendship as a commitment to grow together, even on different paths.
🔹 Growing Apart (and Together) — Why outgrowing people is normal—and how we’ve navigated seasons of distance and reconnection in our own friendship.
🔹 Inner Circle Criteria — Cody’s candid process for moving people from acquaintance to close friend (including the role of "not annoying him").
🔹 The Five’s Castle — Why we’ve built walls around ourselves and what finally helped us start letting people in.
🔹 Loneliness and Belonging — The pain of feeling like we don’t fit anywhere—and how showing up as our full selves changed everything.
🔹 The Power of Ritual — How a weekly ice plunge ritual (yes, seriously) gave Josiah a real-life model for consistent, embodied friendship.
🔹 Letting People Love Us — From church wounds to substance use to old narratives about being “too much,” we explore what’s kept us from connection—and what’s finally helping us open up.
🔹 Practical Steps for Building Friendships — What’s working for us now, from simple check-ins to shared interests to just being a little more brave.

LINKS & RESOURCES:

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🗒️ Full transcript and show notes: enneagramfive.com/44

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📢 What’s your experience with friendship as a Five? Has it come easily, or has it felt like a mystery you’re still trying to solve? Come share your story

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RECOMMENDED NEXT EPISODE:

➡️ #27: Subtypes

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