233. Lessons From 104 Dates with Heidi Friedman

Dating After Divorce

In this heart-to-heart conversation, I sat down with Heidi Freeman, successful attorney and author of "Love Lessons: 104 Dates and the Stories That Led Me to True Love." Heidi shares how turning 40 sparked her quest to understand what true love looks like by interviewing couples in strong relationships. What began as research turned into 11 core themes about authentic connection. With refreshing honesty, Heidi opens up about her 104-date journey, complete with hilarious mishaps, surprising insights, and the beautiful moment when she finally met her husband Will.

This episode cuts through the anxiety about modern dating to remind us that love requires resilience - and is worth 100 disappointing dates.

Key Moments

• Turning 40: Heidi realized she didn't know what true love looked like or felt like and decided to interview couples in solid partnerships
• Research: Heidi interviewed 50+ couples separately to find themes
• Mutual reciprocity: The most impactful insight was how partners take turns supporting each other through life's waves
• The myth of love at first sight: No one Heidi interviewed mentioned this - instead they talked about initial connection and safety
• D04 dates: Heidi shares both hilarious dating disasters and meaningful lessons learned
• Finding Will: How she met her husband through yoga connections and recognized the difference in how she felt
• Dating in the wild vs. apps: The benefits of meeting people through activities vs. online

Quotes

"I had to put on my big girl underwear and go back out there." - Heidi on persevering after dating disappointments

"I think it's not us. This is the way we are socialized...to value relationships, which is awesome. But then we're also socialized to put our own personal value in relationships, and that's what's harmful." - Sade Curry

"Mutual reciprocity and safety... even if you didn't have all the other sprinkles in a relationship, but you had these, you could make a good relationship out of that." - Sade Curry

"What if the next date is him? I would constantly say that to myself when I didn't want to go." - Heidi on staying hopeful

About Heidi:

Heidi Freeman (formerly Goldstein, born Eisman) is a successful attorney and partner at a large law firm specializing in environmental law and social and environmental governance-based counseling. She's written her first book, "Love Lessons," chronicling her dating journey and the relationship insights she gained. Heidi has previously written for Bloomberg Law, 360, and other professional publications. She lives in Cleveland Heights, Ohio with her husband Will and their blended family - two children of her own and two bonus children with Will.

Connect With Heidi

• https://heidifriedman.com
• http://www.instagram.com/lovelessons104
• Podcast: "I Love You More" with her 22-year-old son Zach (available on Spotify and Apple Podcasts)
• Book: "Love Lessons: 104 Dates and the Stories That Led Me to True Love" (Available on Amazon, Barnes & Noble, and Goodreads)

Ready to Transform Your Dating Life?

If this episode resonated with you, I'd love to help you apply these insights to your own dating journey. Book a complimentary dating consultation call with me at sadecurry.com/info and discover how you can build the confidence, clarity, and connection skills to find your perfect match.