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Is true love still possible after 40? Heidi Friedman’s remarkable journey—from her divorce to dating 104 times over ten years—reveals a transformative path to authentic connection and genuine partnership later in life. Drawing from her extensive experiences and interviews with happily married couples, Heidi shares inspiring insights and practical wisdom for anyone navigating love in midlife.

In this candid conversation, Heidi discusses how therapy helped her break patterns and become her own best date before meeting her husband. She recounts hilarious dating disasters—like the date who brought legal documents for her review—and meaningful lessons about what she truly needs in a partner.

Her guiding mantra, “I will be alone before I be with the wrong person,” ultimately led her to discover heartfelt, lasting love.

Highlights & Key Takeaways:

  • Working on yourself first is essential—self-love and confidence attract the right partner.
  • Dating with confidence involves an open heart, multiple avenues, and setting realistic expectations.
  • Approaching dating apps with patience and proper screening can lead to meaningful connections.
  • Becoming your own “best date” prepares you for genuine, fulfilling partnership.
  • Boundaries and taking breaks are crucial for personal growth and clarity.
  • Never ignore red flags—trust your intuition over chemistry or fleeting feelings.

Heidi Friedman Bio

Heidi B. Friedman, formerly Goldstein and born Eisman, is a successful attorney and partner at a large law firm specializing in all areas of environmental law and environmental, social and governance (ESG) based counseling. Love Lessons is her first book, but Heidi has written related to her professional life and experience as a female lawyer.
Heidi lives in Cleveland Heights, Ohio, with her husband Will, and has four children. Two children she birthed, Morgan (25) and Zach (21) and two are her bonus children, Max (28) and Ben (26). In her life, she has a strong network of amazing women who she treasures and who provide support, guidance and company for drinking wine.

Find Heidi Online: Instagram, Website, Buy Book (Amazon)

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Chapters

1. Finding Love in Midlife (00:00:00)

2. The Birth of "Love Lessons" (00:05:14)

3. Dating with Confidence (00:10:22)

4. Navigating Blended Families (00:16:36)

5. Learning to Be Taken Care Of (00:22:01)

6. Modern Dating Across Generations (00:29:33)

109 episodes