Cover image of show Flirt. Fail. Repeat.

Flirt. Fail. Repeat.

Podcast by Rachel

English

Health & personal development

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About 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.

All episodes

20 episodes

episode Little Me, Big Drama (Holiday Teaser) artwork

Little Me, Big Drama (Holiday Teaser)

Before the dating apps and adult chaos, there was me — a ten-year-old with a glitter pen, a Lisa Frank diary, and a lot of feelings. This holiday season, I’m taking a short break from dating disasters to share something a little different: a mini-series of short stories straight from my childhood diaries. Expect bad spelling, big emotions, and the kind of middle-school drama that felt like the end of the world. Plus, a quick life update — my sister is finally welcoming a baby boy after five years of hoping and manifesting, so I’ll be taking some time to soak up all the auntie joy (and baby snuggles). Stay tuned for “Little Me, Big Drama,” dropping soon. Because before I was flirty and failing spectacularly… I was already writing about it.

11 Nov 2025 - 1 min
episode Little Me, Big Drama (Holiday Teaser) artwork

Little Me, Big Drama (Holiday Teaser)

Before the dating apps and adult chaos, there was me — a ten-year-old with a glitter pen, a Lisa Frank diary, and a lot of feelings. This holiday season, I’m taking a short break from dating disasters to share something a little different: a mini-series of short stories straight from my childhood diaries. Expect bad spelling, big emotions, and the kind of middle-school drama that felt like the end of the world. Plus, a quick life update — my sister is finally welcoming a baby boy after five years of hoping and manifesting, so I’ll be taking some time to soak up all the auntie joy (and baby snuggles). Stay tuned for “Little Me, Big Drama,” dropping soon. Because before I was flirty and failing spectacularly… I was already writing about it.

7 Nov 2025 - 1 min
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En fantastisk app med et enormt stort udvalg af spændende podcasts. Podimo formår virkelig at lave godt indhold, der takler de lidt mere svære emner. At der så også er lydbøger oveni til en billig pris, gør at det er blevet min favorit app.
Rigtig god tjeneste med gode eksklusive podcasts og derudover et kæmpe udvalg af podcasts og lydbøger. Kan varmt anbefales, om ikke andet så udelukkende pga Dårligdommerne, Klovn podcast, Hakkedrengene og Han duo 😁 👍
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