EPISODE · Jun 1, 2026 · 51 MIN
Your Most Important Relationship Is With Yourself | Dating in midlife with Kerri Sackville
In this episode of Don't Let the Old Man In, we sit down with Kerri Sackville, author of Out There: A Survival Guide to Dating In Midlife, to unpack the truth about navigating relationships and dating in the next stage of life. We discuss the power of solitude, why people return to dating before they're ready, how to manage your own baggage, and the challenges men in particular face. Suggest a topic for us to cover: https://dontlettheoldmanin.com/suggestions/Subscribe to our newsletter: https://dontlettheoldmanin.com/subscribe/In this episode, we cover:Why dating after divorce demands emotional robustnessThe difference between loneliness and solitude (and why it matters)Why men so often lack emotional support networks post-separationRed flags that reveal themselves on the very first dateHow to build a relationship with yourself before seeking one with someone elseThe honesty test: why it solves 90% of dating problemsWhat midlife dating actually looks like ... without the sugar-coatingCHAPTERS:00:00 Navigating Emotional Needs Post-Separation05:47 The Dynamics of Dating in Midlife11:55 Honesty and Boundaries in Dating17:45 Lessons Learned from the Dating Scene25:18 The Essence of Relationships27:12 The Fear of Solitude30:29 Transformative Alone Time32:30 Self-Discovery Through Solitude36:29 The Impact of Social Media38:10 Understanding Solitude vs. Loneliness39:59 Practical Steps to Embrace Solitude42:11 The Role of Purpose in Life45:01 Navigating Loneliness and Grief48:08 Accepting Aging and Life's Cycles50:27 Finding Meaning in Good MomentsListen to this episode as a podcast: https://linktr.ee/dontllettheoldmanin Hosted on Acast. See acast.com/privacy for more information.
What this episode covers
In this episode of Don't Let the Old Man In, we sit down with Kerri Sackville, author of Out There: A Survival Guide to Dating In Midlife, to unpack the truth about navigating relationships and dating in the next stage of life. We discuss the power of solitude, why people return to dating before they're ready, how to manage your own baggage, and the challenges men in particular face. Suggest a topic for us to cover: https://dontlettheoldmanin.com/suggestions/Subscribe to our newsletter: https://dontlettheoldmanin.com/subscribe/In this episode, we cover:Why dating after divorce demands emotional robustnessThe difference between loneliness and solitude (and why it matters)Why men so often lack emotional support networks post-separationRed flags that reveal themselves on the very first dateHow to build a relationship with yourself before seeking one with someone elseThe honesty test: why it solves 90% of dating problemsWhat midlife dating actually looks like ... without the sugar-coatingCHAPTERS:00:00 Navigating Emotional Needs Post-Separation05:47 The Dynamics of Dating in Midlife11:55 Honesty and Boundaries in Dating17:45 Lessons Learned from the Dating Scene25:18 The Essence of Relationships27:12 The Fear of Solitude30:29 Transformative Alone Time32:30 Self-Discovery Through Solitude36:29 The Impact of Social Media38:10 Understanding Solitude vs. Loneliness39:59 Practical Steps to Embrace Solitude42:11 The Role of Purpose in Life45:01 Navigating Loneliness and Grief48:08 Accepting Aging and Life's Cycles50:27 Finding Meaning in Good MomentsListen to this episode as a podcast: https://linktr.ee/dontllettheoldmanin Hosted on Acast. See acast.com/privacy for more information.
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Your Most Important Relationship Is With Yourself | Dating in midlife with Kerri Sackville
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