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

Enneagram Five

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:

📩 Join the weekly newsletter: enneagramfive.com/newsletter
💬 Join the community: enneagramfive.com/community
🗒️ Full transcript and show notes: enneagramfive.com/44

JOIN THE CONVERSATION:
📢 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 in the community.

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🔹 Practical strategies to stop overthinking and start engaging.
🔹 Growth, connection, and energy management—without the fluff.

👉 Sign up free at enneagramfive.com/newsletter.

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RECOMMENDED NEXT EPISODE:

➡️ #27: Subtypes

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💼 Connect on LinkedIn
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Chapters

1. Introduction and Friendship Beginnings (00:00:00)

2. Defining Friendship (00:01:34)

3. Commitment and Growth in Friendships (00:02:02)

4. Outgrowing Friendships (00:05:01)

5. Friendship and Vulnerability (00:07:00)

6. Childhood and Social Awkwardness (00:15:19)

7. Survival Mechanisms and Social Anxiety (00:17:36)

8. Intentional Connections (00:30:16)

9. The Ice Plunge Community (00:35:31)

10. Bonding Through Shared Experiences (00:40:41)

11. Realizing Self-Imposed Isolation (00:44:30)

12. The Challenge of Authenticity (00:44:59)

13. The Influence of Media on Personal Growth (00:47:15)

14. Emotional Impact of TV Shows (00:48:42)

15. The Role of Vulnerability in Friendships (00:50:30)

16. Substance Use and Authenticity (00:53:31)

17. The Effects of THC vs. Alcohol (00:59:23)

18. Navigating Personal Boundaries (01:02:35)

19. Active Listening and Building Intimacy (01:24:40)

20. Invitation to Join the Community (01:26:49)