Becoming Your Own Best Friend: Cultivating Real Connection and Friendship in Midlife with Cheryl Dillon

What if the reason friendship feels harder in midlife has nothing to do with you, and everything to do with the fact that no one ever told you it would take intention? This week on the Glow Up, Gyrl Podcast, Kyra sits down with Cheryl Dillon, life coach, writer, speaker, and founder of Funderful Experiences, where she helps women create midlife chapters that are joyful, vibrant, and intentional. Cheryl is also the co-founder of Equitable Mediation Services, where she has spent nearly two decades coaching individuals through the emotional complexities of separation and divorce. This conversation is warm, wise, and full of the kind of practical guidance that makes deeper friendship feel possible again, starting with the friendship you have with yourself. In this episode: The delightful breakfast-table story behind the name Funderful Experiences Why making real friendships gets harder in midlife, even when you are surrounded by people The difference between casual socializing and environments where genuine friendship can grow Why one person going first with vulnerability gives everyone else permission What it means to be a friend to yourself, and why it is the prerequisite for real connection Small shifts for moving past small talk: better questions, real stories, genuine interest Why midlife is not a season of decline but the chapter you finally get to write yourself The one thing to do first if you are craving deeper friendships: stop waiting All about the Connected Hearts community and the online version coming soon Whether you are craving deeper friendships, navigating a big transition, or learning to show up as your whole self, this episode will meet you exactly where you are. Learn more: funderfulexperiences.com Join the Connected Hearts waiting list: funderfulexperiences.com (under Connected Hearts) Follow Cheryl: @funderful_experiences Stay connected to Glow Up, Gyrl: Website: glowupgyrl.com | Email: hello@glowupgyrl.com Instagram, TikTok, LinkedIn: @glowupgyrl | Facebook: @glowupgyrlatl Learn more about your ad choices. Visit megaphone.fm/adchoices