Dating in midlife isn’t for the faint of heart. Maybe your marriage or a long-term relationship ended, you’ve healed, and now you’re ready to date again—only to ride a rollercoaster of hope, disappointment, or those “fetal position on your bed” moments we don’t always admit.
But what if dating wasn’t about forcing it or giving up—what if it was about trusting yourself, slowing down, and staying rooted in your worth?
In this episode, I’m joined by Heidi Friedman—an accomplished attorney, writer, and debut author of Love Lessons. After surviving 104 dates (yes, you read that right), Heidi found her “do-over”—a healthy relationship built on mutual respect, care, and real connection. Her journey from single mom to thriving in love is both relatable and inspiring.
We dive into the emotional reality of dating in midlife—what it takes to stay intentional, hold clear relationship expectations, why “don’t settle” isn’t just a slogan, and how to hold onto hope when you’re a single mom dating.
You’ll learn:
- If the 104 dates were worth it
- Why “don’t settle” isn’t just a catchphrase and how to embody it
- How to approach dating as a path to growth, not just a goal
- The mindset shift that kept Heidi open to love
- What intentional dating looks like in practice
- The emotional toll dating can have and how to return to yourself
- What emotional self-care looks like when dating feels discouraging
- How self-work strengthens you for your future partner
If you’ve ever wondered whether love is still possible for you, this conversation proves that it is—and that it can feel better, deeper, and more aligned than ever.
Whether you’re hopeful, healing, or exhausted by dating, this episode will remind you: you deserve love that feels like home.
Cheers to finding love,
Laurie
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