Where can I listen to this podcast?

This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.

Does this podcast accept guests?

No, this podcast does not typically feature guests.

Flirt. Fail. Repeat.

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by Rachel

5.0(4 reviews)

19 episodes

Updated Daily

Accepts GuestsHas Sponsors

Podcast Overview

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.

Language

🇺🇲

Publishing Since

7/15/2025

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Recent Episodes

December 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.

November 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.

November 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.

19 total episodes available

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Frequently asked questions

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What is 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.
How often does this podcast release new episodes?: This podcast updates daily.
Where can I listen to this podcast?: This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
Does this podcast accept guests?: No, this podcast does not typically feature guests.

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