Flirt. Fail. Repeat. is the brutally honest dating podcast for anyone navigating love in midlife with a kid, a history, and a healthy sense of humor. Host Rachel is 40, newly back in the dating world after a 7-year hiatus, and quickly discovering that swiping right comes with more red flags than a parade. From awkward encounters to emotional curveballs, this is real-life dating with none of the filters—just one mom sharing her story, one spectacular fail at a time. If you’ve ever juggled babysitters, bad dates, and late-night overthinking... you’re not alone. Pull up a chair, pour a drink, and get ready to flirt, fail, and laugh your way through it.
I redownloaded Tinder and instantly remembered why I deleted it. In this episode, I dive into my return to the apps after 7 years, share a truly cringe dating story, define some red-flag dating terms, and learn that dating again is the emotional whiplash nobody asked for.
Flirt. Fail. Swipe. Repeat.
Let’s take a walk down memory lane—past the questionable hookups, toxic situationships, and one very real relationship that turned into motherhood. This is my dating résumé: heavy on red flags, light on actual romance, and somehow still funny in hindsight.
In this quick teaser, I’m setting the stage for Flirt. Fail. Repeat.—a brutally honest, slightly unhinged look at dating in your 40s as a single mom who’s been out of the game for way too long.
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I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!