Real Love: Lessons from 104 Dates (w/ Heidi Friedman)

Send us Fan Mail Finding real love starts with learning how to love yourself first. Healing, rebuilding confidence, and opening your heart after heartbreak can feel daunting, but it’s also where the most beautiful stories begin. In this episode, I’m speaking with Heidi B. Friedman, attorney and author of Love Lessons: 104 Dates and the Stories That Led Me to True Love, about what she discovered through the often messy, funny, and revealing process of dating after divorce. Heidi shares how saying yes to new experiences, breaking old rules, and stepping beyond her comfort zone led her to unexpected connections, and ultimately, to her husband. If you’ve ever wondered how to start again or feared it’s too late for love, this conversation is your gentle nudge to keep your heart open, trust the process, and be brave enough to let love find you. Song of the week: Real Love by Mary J. Blige Topics Covered: 00:00:00 – Episode snippet 00:01:56 – Introducing our guest, Heidi Friedman 00:03:25 – Choosing independence and self-worth 00:07:05 – Letting go of the “Fixer” Mindset 00:12:19 – Dating as a journey of self-discovery 00:15:12 – Researching lasting love through interviews with couples 00:17:10 – Writing Love Lessons to guide her children 00:21:09 – Taking turns supporting each other in love 00:23:21 – Open heart and open mind 00:27:55 – Let luck play a role in love 00:30:06 – Break rigid dating rules 00:36:19 – Biggest lesson: Don’t settle 00:41:10 – Be brave 00:42:40 – Where to find Heidi and her book Key Takeaways: "What therapy did for me was create an awareness about my inability to see that I was worthy of an equal partner who I could rely on and who can support me." About Our Guest: Heidi B. Friedman is an accomplished attorney, author, and partner at a leading law firm specializing in environmental law and ESG-based counseling. After 104 dates and nearly a decade of single life, she found love again and penned her debut book, Love Lessons, sharing wisdom from her journey of rediscovery. Connect with Heidi B. Friedman: Web: https://heidifriedman.com/ IG: https://www.instagram.com/lovelessons104 Spotify: https://open.spotify.com/playlist/3ViNW35LJ75ilXd360Yqcl About Your Host Dr. Nicole is a pediatrician, the owner of a successful healthcare consulting company, a riveting keynote and TEDx speaker, and the mom of two beautiful young adult daughters. From the outside, she appeared to have it all. But in 2023 she faced the most difficult challenge of her life- ending a 28-year marriage and navigating heartbreak, deception, and loss. Dr. Nicole is committed to creating a safe space where other women who have experienced a “divine disruption” can heal, recover, and THRIVE! Connect with Dr. Nicole: Web: https://yournextchapter.co/ IG: https://www.instagram.com/yournextchapter_co FB:https://www.facebook.com/yournextchapter.co Join our Email Community Join our community to receive our newsletters and to be the first to hear about exciting announcements and opportunities to connect. The doors for the R&R Collective will reopen in 2026. Join the waitlist today! https://yournextchapter.myflodesk.com/u4ehbbody9 Support the show