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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Contact path
Verified email
Booking probability
20%
Guest openness
Selective
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Signup to Generate a PitchFlirt. 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.
Flirt. Fail. Repeat. is hosted by Rachel. The show has published 20 episodes to date.
Recent episodes include "Little Me, Big Drama: Christmas Entries" (25 December 2025, 9 minutes), "Little Me, Big Drama: The March 1999 Scandal" (20 November 2025, 15 minutes), and "Little Me, Big Drama: My Future Plans" (13 November 2025, 12 minutes).
Flirt. Fail. Repeat. publishes roughly weekly, with episodes averaging 19 minutes across 20 episodes.
Booking probability for Flirt. Fail. Repeat. is 20%, and the host is rated Selective on guests. Flirt. Fail. Repeat. requires a Pod Score of 80 or higher. Flirt. Fail. Repeat.'s contact route on record: verified email.
Rachel hosts Flirt. Fail. Repeat., a society podcast 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...
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...
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...
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...
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...
Episode #14
<p>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...
<p>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...
<p>“Age is just a number”… until you realize he’s still using his college meal plan while you’re shopping for a mortgage. 🥴</p> <p>This week on Flirt. Fail. Repeat., we’re talking age-gap dating: power dynamics, cougar...
Episode #11
<p>Dating is messy enough… but what happens when you let Reddit weigh in?</p> <p>In this episode of Flirt. Fail. Repeat., Rachel dives headfirst into the wild, weird, and sometimes painfully relatable world of Reddit...
Episode #10
<p>We talk a lot about men’s bad behavior in dating (and trust me, they give us plenty of material), but this week we’re turning the mirror around. In this episode of Flirt. Fail. Repeat., Rachel digs into the habits...
<p>From Steve Harvey’s Act Like a Lady, Think Like a Man to Lori Gottlieb’s Marry Him: The Case for Settling for Mr. Good Enough, dating “rules” have long told women to shrink themselves or settle down. But what happens...
<p>He says he’s a “nice guy.” But when the dates end, the masks come off — and suddenly the “friend zone” becomes an excuse, rejection turns into resentment, and “niceness” was never really the point.</p> <p>In this...
<p>This isn’t a typical episode of Flirt. Fail. Repeat.<br> It’s not funny. It’s not flirty. It’s not about ghosting or weird dating app DMs. It’s about the story I’ve carried for 21 years.</p> <p>When I was 19, I was...
<p>From ghosting and group photos to unsolicited trauma dumps and fish pics—this episode is your survival guide to modern dating etiquette. Host Rachel breaks down the do’s, the don’ts, and the “how is this still...
<p>He said I was brainwashed. I said, “Do your own research.”</p> <p>What happens when your date thinks the Earth is flat, gravity doesn’t exist, and Elvis is still alive? In this episode, I unpack the wildest date of...
<p>Why do we chase emotionally unavailable people? Why do we shut down when someone gets too close? And why does a slow reply feel like rejection?</p> <p>In this episode, I dig into the psychology of attachment — and...
Episode #3
<p>He was an hour late to our first date. That should’ve been the red flag — but instead, it was just the beginning.</p> <p>In this episode, I’m sharing one of my first post-hiatus dating experiences, complete with...
Episode #2
<p>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...
<p>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...
Flirt. Fail. Repeat.
<p>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.</p>
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