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Dating Like You Mean It
Dating Like You Mean It
You can hire a VP of Operations, but you’re still swiping like an intern. Let me tell you the truth about my dating journey: For years, I made decisions in love that would have gotten me fired in business. I’ve raised millions, built companies, exited with grace and grit—but in dating?
I was recruiting from a stack of résumés I didn’t remember writing, for roles I didn’t even want, using interview questions I stole from rom-coms and trauma.
I wasn’t dating like a woman who knew herself.
I was dating like a woman who knew who she used to be.
And I couldn’t figure out why it always felt like I was either faking enthusiasm or applying for a role I secretly hoped to lose.
Here’s the punchline
Dating apps are casinos with headshots.
They hijack the same reward systems that slot machines use: intermittent rewards, swipe-based dopamine, and addictive unpredictability.
They make you the product—and they profit from your confusion.
So if you’ve ever caught yourself saying…
“Why do I keep matching with men who don’t get me?”
“I know how to run a team—but I can’t seem to pick a decent date.”
“Why does it feel like no one’s seeing the real me?”
…it’s not because you’re bad at this.
It’s because you’re smart, and you’ve been playing in a rigged system
The Real Cost
Most women I know aren’t scared of rejection.
They’re scared of being loved for someone they’re pretending to be.
And they should be. Because here’s what’s happening:
She builds a version of herself that’s palatable. Softer, cooler, less hungry, more breezy.
She hides the inconvenient truths—her actual standards, her actual body, her actual soul—and then wonders why being seen doesn’t feel safe.
She builds this version of her because it doesn’t hurt when she gets rejected. It’s not really her after all thats being rejected. It’s a creation.
It’s a chicken and egg ladies and the best of us are beginning to see right through it.
She’s not even sure what she wants anymore.
She’s just reacting to what she didn’t want last time.
And now she’s 35, or 45, or 52—not 25, when she last made a real selection.
She’s changed. But her dating criteria haven’t.
She’s operating on legacy code—and it’s crashing.
You are not crazy. You’re under-informed.
Let’s say this clearly:
You’re not too picky. You’re under-aligned.
You’re not flailing. You’re functioning with outdated data.
You’re not behind. You’re on the cusp of doing this with actual consciousness.
Because real talk?
Most of us were taught to date like we were trying to win a prize.
Now we’re the damn prize—and we still haven’t updated our playbook.
Dating Like an Olympic Recruiter
If you were building an Olympic team or hiring a C-suite exec, would you:
Choose someone because they sent an emoji?
Ignore red flags because you were lonely that week?
Confuse “chemistry” with “unhealed pattern recognition”?
No. You’d bring discernment.
You’d know what position you’re hiring for.
You’d test for character, communication, and actual compatibility—not just charm in a tight shirt.
You’d date like you mean it.
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Try This: The Assumption Audit
Before your next swipe, date, or situationship negotiation—pause and ask:
Where did I get my idea of what I want in a partner?
(Parents, exes, media, fear?)When was the last time I updated it?
(Before therapy? Before menopause? Before my last heartbreak?)What traits do I seek because I actually value them—versus because I’ve been taught to?
What assumptions am I making about love, worth, time, and partnership that no longer serve me?
What version of me is doing the choosing?
(The real one, or the one who thinks she has to be smaller, funnier, less intense to be picked?)
If your dating strategy hasn’t evolved since your last major identity shift, it’s not strategy. It’s nostalgia.
And nostalgia doesn’t get you laid or loved the way you deserve.
More Resources for you
📚️ Essential Reading for Dating Sovereignty
"Attached” by Amir Levine & Rachel Heller
The science of attachment styles in relationships. Essential for understanding why you're attracted to unavailable people and how to break the pattern.
"Modern Romance" by Aziz Ansari
Data-driven deep dive into how dating apps and technology have rewired our approach to love and connection.
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📱 Apps & Tools for Strategic Dating
Hinge: "Designed to be deleted" - better conversation starters than mindless swiping.
Bumble: We're not just for dating ... Find someone you actually want to date, then go ahead and Make the First Move.
Feeld: a location-based online dating application aimed at people interested in ethical non-monogamy, polyamory, casual sex, kink, swinging, and other alternative relationship models and sexual preferences.
Gottman Card Decks App: Research-based conversation starters for deeper connection on dates.
🎧 Podcasts for Dating Intelligence
"I want to fit in, but I don’t want to fit in" with Esther Perel
Real therapy sessions exploring relationship patterns, attachment styles, and how past experiences shape current dating choices of a single mom.
Dear Kelsey…
I want to hear from you. Really.
If you’ve:
Dated like a CEO and got ghosted like an intern
Realized your picker was using outdated software
Finally started attracting people who saw you—the full, fierce, sacred you
Tell me. Tell us. Let this be the beginning of something deeper.
Every time you forward this, you help unhook another woman from the idea that she has to contort herself to be loved.
You’re changing culture. One real conversation at a time.
I’m wildly grateful to be in this liberation with you.
In discernment and deep desire,
Liberation Letters. Sex. Soul. Sovereignty.