Friends of Fives: What's it Like to Be Lifelong Friends with an Enneagram 5?

Enneagram Five

Fives often feel like outsiders, but what if the group we’ve always longed for already exists?

In this episode, we invite two longtime friends to join us for a candid conversation about what it’s really like to be friends with a Five. From hilarious stories to hard truths, we explore the highs and lows of maintaining deep, long-term friendships—especially when you tend to live in your head.

We reflect on shared histories, missed connections, and the emotional work required to sustain meaningful relationships over time. If you've ever struggled with investing in friendships, drifting apart from people you care about, or wondering whether you're too much (or not enough), this one is for you.

IN THIS EPISODE:

🔹 Friendship from the Outside In — What it’s like to be friends with a Five, from the perspective of a Seven and a Two.
🔹 Drifting, Reconnecting, and Reconstructing — Why friendships with Fives often fade and rekindle, and what holds them together long-term.
🔹 Anxiety, Energy, and Avoidance — How social anxiety, overthinking, and energy management affect how Fives show up in friendships.
🔹 From Judgement to Acceptance — How shared religious backgrounds shaped our self-righteousness, shame, and eventual emotional growth.
🔹 The Power of Being Seen — Why honest feedback from close friends is vital—and how it can transform your relationship with yourself.

LINKS & RESOURCES:

📩 Join the weekly newsletter: enneagramfive.com/newsletter
💬 Join the community: enneagramfive.com/community
🗒️ Full transcript and show notes: enneagramfive.com/46

JOIN THE CONVERSATION:

📣 What has your experience been like maintaining friendships as a Five? Do you relate to the cycles of connection and withdrawal we talked about? Share your story in the community!

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👉 Sign up free at enneagramfive.com/newsletter.

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RECOMMENDED NEXT EPISODE:

➡️ #27: Subtypes

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Chapters

1. Introduction and Guest Introductions (00:00:00)

2. Discussing Friendships with a Five (00:01:34)

3. Brandon and Cody's High School Memories (00:02:05)

4. Cody Ray's Friendship Journey (00:03:09)

5. Deep Conversations and Self-Discovery (00:03:50)

6. First Impressions and Musical Connections (00:05:22)

7. Reflecting on Friendship Dynamics (00:06:52)

8. Bachelor Party and Transformational Experiences (00:11:52)

9. Challenges and Annoyances in Friendships (00:24:16)

10. Turning Negatives into Positives (00:29:03)

11. The Tendency to Drift Apart (00:29:36)

12. Reconnecting Through Deconstruction (00:30:39)

13. The Effort to Maintain Friendships (00:31:23)

14. The Cyclical Nature of Friendship (00:33:53)

15. Balancing Social Anxiety and Connection (00:38:06)

16. Emotional Growth and Self-Acceptance (00:39:59)

17. Reflecting on Past Judgments (00:42:16)

18. The Importance of Honest Feedback (00:52:01)

19. The Value of Lifelong Friendships (00:57:32)