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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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What happens when you start dating again after 27 years of marriage? Spoiler: it’s awkward, hilarious, a little cringey… and surprisingly fun.
In this episode of An Imperfectly Perfect Life with Shari Leid, I pull back the curtain on what it’s really like to date in midlife — from fish photo profiles 🐟 to first-date experiments and everything in between.
Along the way, I share pieces of my own dating journey and bring in wisdom (and laughs) from:
✨ Justina Chen – award-winning YA author, who knows all about the messy magic of love.
✨ Connie Curlette – psychotherapist and relationship coach, with real tools for navigating dating in midlife.
Whether you’re single, married, divorced, or just here for the laughs, you’ll walk away with stories, strategies, and maybe even a little hope for your own imperfectly perfect adventures.
Grab your coffee or your wine 🍷 (no judgment here) and join me — because dating after divorce? It’s not just about finding someone new. It’s about finding yourself again.
🎥 Want to watch my journey? Subscribe on YouTube at youtube.com/sharileid
💌 And don’t forget to grab my free 52 Weeks of Connection email series—one weekly challenge to help you feel more connected and build real friendships as an adult. It’s free, simple, and you can unsubscribe anytime. Sign up at: https://zc.vg/ZDPo2
And if you’re ready to go even deeper, learn more about my Flip the Box® LIVE - The Connection Conference and Flip The Box® Women's Retreat at https://animperfectlyperfectlife.com/working-together
To purchase my latest book, Table For 51, visit: https://a.co/d/cL7uYIy
Let’s dive in—reinvention, real talk, and a whole lot of laughter start NOW!
#animperfectlyperfectlife #sharileid #newbeginnings #theartofreinvention #lilfecoach #midlifecoach #selfhelp #livewithpurpose #divorce #tablefor51 #50statesproject #flipthebox #keynotespeaker #connectioncoach #belonging #creatingbelonging #keynotespeaker #relocation
Chapters
1. Dating After 27 Years of Marriage (00:00:00)
2. Justina's Dating Strategy Success Story (00:02:04)
3. My 16 First Dates Experiment (00:08:38)
4. Rethinking Marriage as the Ultimate Goal (00:14:11)
5. Recognizing Codependent Behaviors (00:17:03)
6. Dating Advice and Future Plans (00:21:03)
7. Flip the Box Women's Retreat (00:23:07)
74 episodes
