EPISODE · Jul 4, 2026 · 1H 1M
S1 E21 UR Journey of Becoming. What 50 Dates Taught Me About Myself, with Cindy Drummond
from Get UR Sh!t Together With Yana Kasperczak · host Yana Kasperczak
UR Journey of Becoming. What 50 Dates Taught Me About Myself, with Cindy DrummondWhat do you do when the life you built turns out to be built on a lie?Cindy Drummond found out at 47.After nearly a decade with a partner who had been living a secret life . . . . . she packed up her two daughters, moved into her parents' basement, and made a decision that changed everything.She was going to go on 50 dates in 52 weeks.Not to find the one. Not to fill the silence. But because underneath the wreckage of a relationship she had spent years pretending was fine . . . . . she had a feeling that the person she most needed to find was herself.She just didn't know it would take 53 dates to get there.Cindy Drummond is the author of Reflections from the Dating Pool, a bold, heartfelt account of the year she chose herself. With humor, vulnerability, and hard-won insight, Cindy turned real-life dating into powerful reflections on courage, boundaries, resilience, and self-worth.In this conversation she shares:What those 50 dates actually taught her (and why it had almost nothing to do with the men)The biggest lie she had been living: pretending everything was fine when something inside her always knew it wasn'tWhat she discovered in the in-between moments, the quiet drive home after each date, the sitting with herself when there was no distraction left, and why that is where the real growing happenedHow she went from naive and judgmental to empathetic and open . . . . . one date at a timeThe difference between being alone and being lonely, and why she had to learn it the hard wayThe Good Girl Syndrome, losing her voice, and what it actually took to find it againA 30-year friendship that ended when she needed it most, and what grief like that teaches youWhy sometimes you have to die to an old version of yourself before a truer one can come throughThis episode is for the woman who:🖤 Has been pretending everything is fine when something inside her knows it is not🖤 Has confused being alone with being lonely and is terrified of the quiet🖤 Has been so busy being good that she forgot to be honest🖤 Is sitting in her own ache right now and needs to know the hurting is actually the becomingYOLO and Resilient.That is how Cindy describes her journey of becoming.And it took 53 dates . . . . . not 50 . . . . . to find out why.Subscribe so you never miss an episode of UR Journey of Becoming inside Get UR Sh!t Together with Yana Kasperczak.👇 Resources and LinksFind Cindy on Instagram . . . . . @cindydrummondyycFree Clarity Call with Yana . . . . . https://schedule-with-yana.as.me/15MinuteClarityCallExplore all resources, programs, and community . . . . . https://linktr.ee/empathunicornacademy
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S1 E21 UR Journey of Becoming. What 50 Dates Taught Me About Myself, with Cindy Drummond
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