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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.
Required Pod Score for this show. PitchCentric checks your profile against host openness, topical fit, and audience signals before you generate a pitch.
Contact path
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Booking probability
24%
Guest openness
Selective
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Signup to Generate a PitchFlirt. Fail. Repeat. is a society podcast hosted by Rachel, with 20 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.
Rachel hosts Flirt. Fail. Repeat., a society show with 20 episodes published.
Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.
Episode #18
<p>In this holiday mini-episode, I read a handful of short, matter-of-fact diary entries I wrote around Christmas. They’re simple, honest, and unintentionally funny — a tiny snapshot of childhood holidays, feelings, and festive chaos. Cozy, nostalgic, and just a little dramatic… of course.</p>
Episode #19
<p>In this episode, I read an epic diary entry from March 1999, when 13-year-old me kissed a boy my best friend liked… and then documented it like I was living in a Victorian tragedy. It’s emotional, it’s poetic, and it’s way too dramatic for a cafeteria-adjacent romance.</p>
Episode #16
<p>When I was ten, I had very specific ideas about my future — and spoiler alert: none of them included being a 40-year-old single mom with a podcast called Flirt. Fail. Repeat.</p> <p>In this first installment of Little Me, Big Drama, I dust off my childhood diary to revisit my list of “Future Plans” — a masterpiece of ambition, delusion, and glitter gel pen dreams. From my plans to become an environmental activist to the first woman presidents, it’s a chaotic peek into my younger brain… and a reminder that adulting didn’t exactly go to plan.</p> <p>Because befo...
Flirt. Fail. Repeat.
<p>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.</p> <p>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.</p> <p>Plus, a quick life update — my sister is finally welcoming a baby boy after five years of hoping and manifesting, so I’ll be takin...
Flirt. Fail. Repeat.
<p>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.</p> <p>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.</p> <p>Plus, a quick life update — my sister is finally welcoming a baby boy after five years of hoping and manifesting, so I’ll be takin...
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Based on semantic analysis of episode topics and host coverage, this show is a strong guest fit for executives in:
Industry fit is computed by PitchCentric using vector embeddings of the show's episode catalog.
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