Flirt. Fail. Repeat.
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.
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Episodes
4 days ago
4 days ago
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.
Thursday Jul 17, 2025
Thursday Jul 17, 2025
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.
Tuesday Jul 15, 2025
Tuesday Jul 15, 2025
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.