Flirt. Fail. Repeat.

Rachel
  • 5.0 (4)
  • RELATIONSHIPS
  • UPDATED WEEKLY

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.

  1. 12/25/2025

    Little Me, Big Drama: Christmas Entries

    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.

    9 min

  2. 11/20/2025

    Little Me, Big Drama: The March 1999 Scandal

    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.

    15 min

  3. 11/13/2025

    Little Me, Big Drama: My Future Plans

    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. 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. Because before I was flirty and failing spectacularly — I was just a kid with a diary and a lot of unrealistic goals.

    12 min

  4. TRAILER

    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.

    2 min

  5. TRAILER

    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.

    2 min

  6. 11/06/2025

    Dating in the Age of TikTok Advice

    Everyone’s suddenly a relationship expert—especially on TikTok. From “high-value woman” commandments to “masculine energy” manifestos, Rachel dives into the chaos of online dating advice. Join her as she scrolls through the noise, calls out the contradictions, and laughs at the absurdity of trying to find love in an algorithm.

    21 min

  7. 10/30/2025

    Dating Horror Stories — Ghosts, Ghouls & Guys Named Greg

    This Halloween, Rachel opens the crypt of modern dating to share her creepiest encounters, listener-submitted horror stories, and chilling true crime cases of online dating gone wrong. From ghosting to genuine ghouls, it’s a spooky mix of humor, heartbreak, and final girl energy. 💀 Trigger Warning: This episode includes discussions of real-life violence and murder related to true crime dating cases, which may be disturbing to some listeners. ☕ Grab your pumpkin spice, lock your doors, and prepare to flirt… if you dare.

    18 min

  8. 10/23/2025

    The Age Gap Episode: Cougars & Cradle Robbers?

    “Age is just a number”… until you realize he’s still using his college meal plan while you’re shopping for a mortgage. 🥴 This week on Flirt. Fail. Repeat., we’re talking age-gap dating: power dynamics, cougar labels, and my own spectacular fails. Plus, Leo’s 25-year rule, Demi & Ashton drama, and why Priyanka & Nick are proof it can work.

    27 min
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Trailers

Ratings & Reviews

5
out of 5
4 Ratings

About

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.

Information

  • Creator
    Rachel
  • Years Active
    2K
  • Episodes
    20
  • Rating
    Explicit
  • Copyright
    © Copyright 2025 All rights reserved.
  • Show Website
    Flirt. Fail. Repeat.