Flirt. Fail. Repeat.

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 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.

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.

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.

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 listeners.
☕ Grab your pumpkin spice, lock your doors, and prepare to flirt… if you dare.

“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 little secondhand embarrassment, and plenty of reminders that no matter how bad your last date was, someone on Reddit has it worse.

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 conversation is equal parts funny, raw, and a little uncomfortable. Because sometimes, our biggest enemy in dating isn’t the guy across the table—it’s us.