This Empty Nest Life

108. 104 Dates: A Midlife Journey to Authentic Love


Listen Later

Send Jay comments via text

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)

Support the show

FREE WORKBOOK
3 Steps to Loving Your Empty Nest Life

ENJOY THE SHOW?
Don’t miss an episode, subscribe via Apple Podcasts or follow on Spotify and many more.

LOVE THE SHOW?
Get your THIS EMPTY NEST LIFE swag

Review us on Love the Podcast, Apple Podcasts, or Spotify -- reviews and ratings help others find us and we’d appreciate your support greatly.

CONNECT WITH JAY
Email, LinkedIn, Instagram, or TikTok

...more
View all episodesView all episodes
Download on the App Store

This Empty Nest LifeBy Jay Ramsden

  • 5
  • 5
  • 5
  • 5
  • 5

5

15 ratings


More shows like This Empty Nest Life

View all
Hidden Brain by Hidden Brain, Shankar Vedantam

Hidden Brain

43,643 Listeners

The One You Feed by Eric Zimmer

The One You Feed

2,560 Listeners

10% Happier with Dan Harris by 10% Happier

10% Happier with Dan Harris

12,764 Listeners

The Lazy Genius Podcast by Kendra, The Lazy Genius

The Lazy Genius Podcast

6,598 Listeners

Pod Save America by Crooked Media

Pod Save America

87,199 Listeners

The Daily by The New York Times

The Daily

112,376 Listeners

For The Love With Jen Hatmaker Podcast by Jen Hatmaker

For The Love With Jen Hatmaker Podcast

6,452 Listeners

the goop podcast by gwyneth paltrow

the goop podcast

6,793 Listeners

SmartLess by Jason Bateman, Sean Hayes, Will Arnett

SmartLess

58,278 Listeners

The Mel Robbins Podcast by Mel Robbins

The Mel Robbins Podcast

20,193 Listeners

The Loud Quiet - Empty Nest Living by Rick and Clancy Denton

The Loud Quiet - Empty Nest Living

9 Listeners

Good Hang with Amy Poehler by The Ringer

Good Hang with Amy Poehler

9,604 Listeners

Life After Launch: Tools for coping with the empty nest, navigating midlife transitions, and parenting adult children. by Allison Goldberg

Life After Launch: Tools for coping with the empty nest, navigating midlife transitions, and parenting adult children.

16 Listeners