EPISODE · Apr 2, 2026 · 38 MIN
Ep 22: Top 3 Post-Divorce Dating Mistakes That Miss the Right Man
from Love At Any Age with Laurie Gerber · host Laurie Gerber
What if the biggest mistake you could make after divorce is the exact one most women make on day one? A newly divorced mom went from dating nightmare after nightmare to finding a love that still feels right 11 years later, and she shares exactly what changed. Laurie Gerber sits down with Jackie Pilossoph, founder of Divorced Girl Smiling, for a conversation about dating after divorce, rebuilding confidence, post-divorce healing, and what it means to choose yourself first. Jackie opens up about the mistakes she made early on, the personal growth that reshaped her dating choices, and how she ultimately created a healthy, lasting relationship later in life. Her story offers grounded hope for women over 50 who want love that feels steady, mutual, and real. In this episode, Laurie and Jackie get into: ✅ The post-divorce decision that feels right but derails healthy dating ✅ The 4 types of men on dating sites and which ones waste years ✅ The moment she stopped chasing love, and how everything shifted ✅ The formula for balancing friendship, respect, and chemistry ✅ 9 signs of a healthy relationship ✅ The blended-family challenge that could have broken it, but didn’t, and why Timestamps 00:02:10–05:51 — The First (and Costliest) Mistake Post-Divorce. 00:05:51–10:44 — The Gap Year, and the Four Types of Men Online. 00:10:44–17:37 — The 3 Steps That Changed Everything. 00:17:37–21:53 — Forgiving Yourself and Rethinking Baggage. 00:21:53–30:15 — The Click: Meeting Her Partner of 11 Years. 00:30:15–34:48 — Knowing He Was the One, and Blended Family Reality. Links & Resources Divorce Girl Smiling: https://www.divorcedgirlsmiling.com Jackie’s Book: https://www.divorcedgirlsmiling.com/who-let-the-dogs-out-book/ If you want clarity on what a healthy partnership looks like for you, I walk you through the 3H method step by step in my free 75-minute training: 👉 https://www.lauriegerber.com/webinar Stay connected with Laurie YouTube: https://www.youtube.com/@lauriegerbercoach Instagram: https://www.instagram.com/lauriegerber_coach/ Facebook: https://www.facebook.com/lauriegerberdatingcoach LinkedIn: https://www.linkedin.com/in/lauriegerber Podbean: https://lauriegerbercoach.podbean.com/
What this episode covers
What if the biggest mistake you could make after divorce is the exact one most women make on day one?A newly divorced mom went from dating nightmare after nightmare to finding a love that still feels right 11 years later, and she shares exactly what changed.Laurie Gerber sits down with Jackie Pilossoph, founder of Divorced Girl Smiling, for a conversation about dating after divorce, rebuilding confidence, post-divorce healing, and what it means to choose yourself first.Jackie opens up about the mistakes she made early on, the personal growth that reshaped her dating choices, and how she ultimately created a healthy, lasting relationship later in life. Her story offers grounded hope for women over 50 who want love that feels steady, mutual, and real. In this episode, Laurie and Jackie get into:✅ The post-divorce decision that feels right but derails healthy dating✅ The 4 types of men on dating sites and which ones waste years✅ The moment she stopped chasing love, and how everything shifted✅ The formula for balancing friendship, respect, and chemistry✅ 9 signs of a healthy relationship ✅ The blended-family challenge that could have broken it, but didn’t, and why Timestamps00:02:10–05:51 — The First (and Costliest) Mistake Post-Divorce.00:05:51–10:44 — The Gap Year, and the Four Types of Men Online.00:10:44–17:37 — The 3 Steps That Changed Everything.00:17:37–21:53 — Forgiving Yourself and Rethinking Baggage.00:21:53–30:15 — The Click: Meeting Her Partner of 11 Years.00:30:15–34:48 — Knowing He Was the One, and Blended Family Reality. Links & ResourcesDivorce Girl Smiling: https://www.divorcedgirlsmiling.comJackie’s Book: https://www.divorcedgirlsmiling.com/who-let-the-dogs-out-book/If you want clarity on what a healthy partnership looks like for you, I walk you through the 3H method step by step in my free 75-minute training:👉 https://www.lauriegerber.com/webinar Stay connected with LaurieYouTube: https://www.youtube.com/@lauriegerbercoachInstagram: https://www.instagram.com/lauriegerber_coach/Facebook: https://www.facebook.com/lauriegerberdatingcoachLinkedIn: https://www.linkedin.com/in/lauriegerberPodbean: https://lauriegerbercoach.podbean.com/
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Ep 22: Top 3 Post-Divorce Dating Mistakes That Miss the Right Man
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