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.
Episodes
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.
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.
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 presid...
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 u...
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 u...
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.
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...
“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.
Dating is messy enough… but what happens when you let Reddit weigh in?
In this episode of Flirt. Fail. Repeat., Rachel dives headfirst into the wild, weird, and sometimes painfully relatable world of Reddit dating stories. From “Am I the Asshole?” threads to questionable relationship advice and red-flag confessions, we’re pulling the juiciest posts straight from the internet’s most opinionated comment section.
Expect laughs, a litt...
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, mindsets, and red flags that women bring to the table—yes, even the ones we’d rather not admit to.
From “pick-me” girl tendencies to ignoring red flags, self-sabotage, and the myths we cling to about love, this conversat...
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 when those outdated ideas evolve into today’s toxic manosphere?
In this episode, I’m breaking down the old-school dating advice that shaped the 2000s, the rise of “red pill” lingo and self-proclaimed “high-value men,” ...
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.
In this episode, I’m pulling apart the Nice Guy™ Delusion — why so many men wear it like a badge of honor, how entitlement hides beneath the surface, and why the mythical “friend zone” is one of dating’s most toxic lies.
From my own stor...
This isn’t a typical episode of Flirt. Fail. Repeat. 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.
When I was 19, I was sexually assaulted by two men I knew and trusted. I didn’t report. I didn’t tell many people. I just tried to survive. And for a long time, I thought silence was safer. But silence never protected me. It protected them.
This episod...
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 happening?” of dating in 2025.
We cover everything: ✔️ First message fails ✔️ Profiles that give the ick ✔️ Real-life date behavior red flags ✔️ What to do after the date (spoiler: text back, Brian)
Whether you're swiping...
He said I was brainwashed. I said, “Do your own research.”
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 my life, dive into the psychology of conspiracy theorists, and share exactly why “we’d be better as friends” was the understatement of the year.
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?
In this episode, I dig into the psychology of attachment — and how the way we were parented can shape the way we date. I share my own story of growing up without maternal love, talk about recreating those patterns in adult relationships, and how I’m breaking the cycle for myself and my daug...
He was an hour late to our first date. That should’ve been the red flag — but instead, it was just the beginning.
In this episode, I’m sharing one of my first post-hiatus dating experiences, complete with emotional manipulation, entitlement, and a truly spectacular lack of self-awareness. We’re breaking down modern dating red flags, defining a few you might be missing, and playing a game of “Flag or No Flag?” (Spoiler: most of them...
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 dating again is the emotional whiplash nobody asked for.
Flirt. Fail. Swipe. Repeat.
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 romance, and somehow still funny in hindsight.
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.
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