Flirt. Fail. Repeat.
Rachel
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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…
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,…
S1E16 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…
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…
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…
S1E14 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…
S1E13 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…
S1E12 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…
S1E11 Dating Disasters: As Told by Reddit
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…
S1E10 Our Own Worst Enemies: Women’s Dating Habits
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…
S1E9 Dating Rules, Settling, and the Manosphere Mess
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.…
S1E8 The Nice Guy Delusion: Dating, Ego & the Friend Zone Lie
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…
S1E7 When Silence Isn’t Safe: Survival, Power & the System That Fails Us
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…
S1E6 Don’t Be Weird, Brian: A Guide to Dating Etiquette
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…
S1E5 Dating a Flat Earther: A Love Story (Kind Of)
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…
S1E4 Why Am I Like This? (The Attachment Episode)
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…
S1E3 Red Flags & Other Dating Delusions
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…
S1E2 Who gave me a Tinder account?
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…
S1E1 Ghosted, Gaslit, Knocked Up: A Dating Origin Story
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…
S1 Flirting with Disaster: A Teaser
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.
Frequently Asked Questions
Flirt. Fail. Repeat. has published 20 episodes since July 2025, covering topics in Relationships, Society & Culture.
Flirt. Fail. Repeat. is currently dormant with new episodes weekly. Average episode length is 21m.
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