This week’s episode dives into the quiet shame so many people carry about their relationship history — whether they’ve never had a long-term partnership, stayed too long in the wrong one, or feel stuck repeating the same painful patterns.
Inspired by a vulnerable clip from American Author Simon Sinek, we explore the assumptions society places on romantic timelines, why people judge themselves so harshly, and what our patterns are actually trying to show us.
Todd brings the lens of a long-married couples therapist; I bring the lived experience of someone whose path looks a lot more like Simon’s. Together, we unpack why these stories form, how they shape the way we date, and what it really takes to build healthier connections, without shame steering the process.
You’ll learn how to:
Recognise the hidden shame behind questions like “Why haven’t you been married yet?”
Understand the emotional patterns underneath both commitment avoidance and staying too long in unhealthy relationships
Reframe your relationship history without pathologising yourself
Identify where you may be attracting mirrors of your own unresolved wounds
Build the courage to step out of familiar patterns and communicate more openly
Stop seeing yourself as “the problem” and become more intentional about the connections you create
Why this matters
We live in a culture that tends to treat romantic milestones like checkboxes: marriage means success, singlehood means deficiency, and long-term relationships count more than emotional wellbeing. Those narratives create shame on both ends: the person who can’t seem to “make it work,” and the person who can’t seem to leave.
This episode challenges those assumptions and brings compassion back into the conversation. When you understand what’s driving your patterns (fear, loyalty, family roles, wounds you learned to carry), you stop blaming yourself and start working with what’s true.
We believe emotional awareness is the new revolution, and we hope this conversation offers new perspectives that help you tune into what feels true to you.
Timestamps
00:00 — Intro
01:00 — The Simon Sinek clip that sparked this conversation
03:00 — Why society judges single people so harshly
06:00 — Dannie’s experience with subtle social shame
08:00 — Avoidant vs. anxious patterns: neither is “the villain”
12:30 — What’s really behind the label “commitment issues”?
15:30 — The internal narrative that keeps us stuck
18:00 — How self-work can shift your relationship patterns
21:00 — The “right person” vs. the person who teaches you what you need
24:30 — Why people stay in unhealthy relationships
30:00 — The real cost of staying where you’re already lonely
33:00 — Questions to ask yourself from both sides of the struggle
35:00 — Closing reflections
💬 Your turn to reflect
What story do you tell yourself about your relationship history — and what might change if you told it with compassion instead of shame?
📩 If this episode resonated, we’d love you to share it with someone who might need the reminder that there is nothing wrong with them.
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Resources & Mentions
Simon Sinek full podcast interview: You’ll fail at love… until you realise this.
Simon Oliver Sinek is an American author and inspirational speaker on business leadership. His books include Start with Why (2009) and The Infinite Game (2019).
