Flirt. Fail. Repeat.

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 But what happens when those outdated ideas evolve into today’s toxic manosphere?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,” and why the friend zone and “nice guy” narratives are anything but harmless. I’ll share my own stories — from being dumped for being “too smart and successful” to recent “nice guys” who weren’t so nice after all — and pair them with hard stats showing why single women are thriving.
Because if settling means silencing yourself, and dating rules mean contorting into a pick-me, I’d rather stay single, sarcastic, and spectacularly myself.
💌 Share your dating fails at flirt.fail.repeat@gmail.com📲 Follow me on Instagram @Flirt.Fail.Repeat and Facebook at Flirt Fail Repeat

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 stories of so-called “nice guys” who revealed themselves to be anything but, to the cultural myths that fuel this behavior, to the tragic ways it can escalate when rejection is taken as a personal attack — we’re breaking it all down.
Because being kind isn’t transactional. Respect isn’t leverage. And the “friend zone”? It was never real.
💌 Share your own dating fails at flirt.fail.repeat@gmail.com📲 Follow me on Instagram @Flirt.Fail.Repeat and Facebook at Flirt Fail Repeat

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 episode dives into:— My story, and why I’m finally sharing it— The headlines that pushed me to speak (Epstein, Diddy, Trump, and more)— Why women are still killed for saying “no”— The systems that fail survivors again and again— And how we take our voices back
Trigger warning: This episode contains discussion of sexual assault, trauma, and intimate partner violence.
Resources for Survivors:
RAINN: 1-800-656-HOPE or rainn.org
National Sexual Violence Resource Center: nsvrc.org
National Domestic Violence Hotline: 1-800-799-SAFE or thehotline.org
Crisis Text Line: Text HOME to 741741

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, soft launching, or just here for the group chat gossip—this one’s for you.
Listen now. Learn the etiquette. And please, don’t be weird.

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 daughter.
Flirt. Fail. Heal. Repeat.

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 are flags.)
Flirt. Fail. Swipe. Repeat.

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.