Podcast Summary: Ready For Love with Hilary Silver

Episode #94: Dating After Loss—How Charlene Found Real Love Again
Release Date: December 12, 2025
Host: Hilary Silver (Cloud10)
Guest: Charlene, Ready for Love alum, transformational health and life coach

Episode Overview

This episode centers on dating after significant loss and personal transformation. Host Hilary Silver interviews Charlene, an alumna of the Ready for Love program. Charlene shares her journey through grief following the deaths of her husband and both parents, her challenges in reentering the dating world, and the pathway to rediscovering herself and finding authentic love again. The conversation provides hope, practical insight, and empowering strategies for women navigating love, loss, and personal growth.

Key Discussion Points & Insights

1. Charlene’s Backstory: Grief and Wanting More

• [03:20] Charlene recounts the loss of her husband to cancer after a difficult illness and the subsequent deaths of both parents in the span of three years.

• She describes moving through different forms of therapy, ultimately realizing she still hadn’t truly healed when she tried dating again.

  “It was a rough three years. My mom, my husband, and then my dad. So three paramount people died in my life.” — Charlene [03:29]

• [05:15] Attempting to date prematurely, Charlene found herself attracting emotionally unavailable men with their own baggage, ultimately seeing her desperation mirrored back to her.

  “I was attracting men who were in the middle of divorces… emotionally unavailable, the whole nine yards. That was my big thing.” — Charlene [05:38]

2. The Truth about Widowhood and Relationships

• [06:22] Hilary talks about the diversity of widow experiences and the importance of NOT assuming that every widow is steeped only in grief.

• [09:05] Charlene discusses her tumultuous marriage, a dynamic of highs and lows, unmet needs, and her pattern of seeking affirmation externally.

  “I realized one of my big things was I was always looking outside instead of looking inside for affirmation… I was always hungry for that, and he provided that.” — Charlene [09:19]

• Charlene reflects on how, despite deep friendship, her marriage was characterized by cycles of clinging, manipulation, and her own diminishing sense of self.

• The experience of illness and loss eventually led to profound moments of connection and compassion.

  “When he got sick… for the first time in 12 years, that man leaned into me, and I was like, oh, there you are. I’ve been looking for you the entire… where the hell have you been?” — Charlene [10:51]

3. Recognizing and Repeating Patterns

• [14:23] Back in the dating world, Charlene finds herself falling into old patterns—attracting “people like him” and reliving past dynamics.

• She acknowledges the “blind spots” in repeating relationship cycles, and her need for help to interrupt them.

  “I’m attracting people like him… it was so intense. I’m going down the same rabbit hole… but I don’t know what to do about it. I need help.” — Charlene [14:23]

4. The Transformation: Tools and Learning from the Program

• [16:39] Charlene credits several program tools for her transformation:

  • Sunny Side Up Model: A visual metaphor (two fried eggs) for healthy relationships; helps women see how to “coexist together and stay exactly who you are” [16:39].
  • Ownership and Self-Awareness: Confronting patterns of seeking external validation, abandonment fears, and never asking herself what she truly wants.
  • ACE Conversations: Dialogues with her inner child, reparenting herself, and healing core wounds.

  “[The program] provides such great tools that just become part of your identity… I fell in love with myself in this program. I’m fucking awesome!” — Charlene [19:33]

• [19:33] A major breakthrough: realizing she had never defined her own values or non-negotiables in a partner. Doing this exercise “took three weeks” but completely shifted how she approached dating.

• [22:44] Living authentically and setting boundaries—“I’m living for me and I’m doing what I want to do.”

5. Love, Boundaries, and New Relationships

• [28:19] Charlene describes dating with newfound clarity, attracting higher-quality men, and—crucially—walking away if things didn’t align (even from “great” guys if the chemistry or values weren’t there).

  “We are abundant. We are a banquet. We’re not getting crumbs. We’re going for the whole fricking thing.” — Charlene [29:12]

• [29:57] She finds a partner who aligns with her values, encourages her creativity, and with whom she experiences “heat, heart, and head” all together.

• She emphasizes living in the moment—“no rush, not worried about outcomes,” and enjoying the freedom and joy of authentic connection.

6. Lasting Impact and Advice for Listeners

• [34:57] For women “on the fence” about doing the work:

  • Charlene urges courage, self-compassion, and taking up space in the world with authenticity.

  “If you’re on the fence, cross over… let the courage take grip… your whole life is going to change… you will be a force of love and nature that attracts exactly what you want.” — Charlene [34:57]

• [36:12] She frames her journey as a reclamation of selfhood and abundance, a process leading not just to love, but to living life fully.

  “After [my husband] died, there was a time I was ready to take myself out, but I woke up and said, no, I want to live. And this is living. This is absolute living.” — Charlene [36:45]

Notable Quotes & Memorable Moments

• “[My] light just got dimmer and dimmer and dimmer because I allowed that to happen… I owned that.” — Charlene [09:50]
• “I have this impervious, you know, space… mine is like this little warm space with a fireplace and books… people can come visit, you can come and go.” — Charlene [19:45]
• “You gave me the tools to change my life in a way that I was… I wasn’t doing. I wasn’t enacting it. And you created a program that made it possible.” — Charlene to Hilary [27:52]
• “He’s just the cherry on top, really... if it doesn’t work out I’m going to be fine because I’ve got me. I’m my best friend.” — Charlene [33:50]
• “Take up space, girl. Damn right to take up space… this will teach you how to live fully.” — Charlene [36:12]

Important Timestamps & Segment Highlights

• Charlene’s story of loss, therapy, & realizing she wasn’t healed: [03:20]–[05:19]
• Discussion of widowhood’s complexities: [06:22]–[09:05]
• Unpacking the pattern of external validation & tumultuous marriage: [09:05]–[13:38]
• Realization of repeating relationship patterns after loss: [14:23]–[15:47]
• Transformation via the Ready for Love program & key tools: [16:39]–[19:33]
• Breakthroughs—self-love, boundaries, authenticity: [19:34]–[22:44]
• Manifesting a healthy relationship, valuing self, and practical dating changes: [28:19]–[33:41]
• Living in abundance & giving advice to listeners: [34:57]–[36:45]

Episode Takeaways

• Deep transformation, not dating “tips,” is what creates lasting change in love and life.
• True healing after loss requires honest self-reflection, not just time or surface-level therapy.
• Creating and living by your values and non-negotiables transforms relationship dynamics.
• Authentic self-love and boundaries attract partners who align with your best self.
• It’s never too late to reclaim your life, your joy, and create the love (and life) you want.

For those navigating love after loss or wanting real change in how they show up for themselves and their relationships, this conversation is rich with authentic inspiration, practical tools, and a reminder: you are your best investment, and the right love follows when you love yourself first.