30: 104 Love Lessons- Finding True Love in Midlife with Heidi Friedman

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What if your path to real love started with an honest confession: I don’t know what love really feels like? That’s where attorney and author Heidi B. Freeman began, turning a divorce into a decade-long experiment in connection—104 dates, interviews with couples across ages and backgrounds, and a journal that captured both the loneliness and the breakthroughs that followed. We walk through her most hard-won lessons, the ones that turned frustration into clarity and eventually into a marriage that fits.

We unpack the difference between standards and rules, and why dropping rigid limits can open doors you didn’t know existed. Heidi shares why “don’t settle” isn’t a slogan but a practice: short first meetings, honest no’s instead of ghosting, and listening to red flags before they cost you years. We talk about being happy alone without closing your heart, using dating apps as practice while prioritizing real-life chemistry, and how to expand your circle beyond the friends who already know you. There’s also a candid look at blended families, co-parenting values, and the kind of partner who supports your ambitions instead of shrinking them.

Threaded through the story is a reminder that luck and timing matter—but only when you’re in motion. From yoga studios to running groups to chance introductions, Heidi shows how showing up creates serendipity. If you’re starting again, dating in midlife, or trying to strengthen the relationship you’re in, you’ll leave with a practical toolkit: be the partner you seek, trust your gut, say what you mean, and keep your world big. Enjoy the conversation, then share it with someone who needs a nudge to believe that better love is possible. If you did, would you stop and take five minutes to leave me a review on Apple Podcasts?
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Love Lessons book: Love Lessons: 104 Dates And The Journey That Led Me To True Love available on Amazon now
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Podcast: I Love You More on Spotify and Apple