Episode 1: Don’t F*ck Your Boss!
Today’s lesson is simple: don’t f*ck your boss.
The Story That Sparked It (Yes, It’s Real)
One of us worked with a waitress who decided to hook up with her married boss.
Fast-forward:
marriage destroyed
kids involved
she gets pregnant
he leaves his wife
it becomes a full-on workplace telenovela
everyone suffers except the gossip circle
It wasn’t romantic. It wasn’t empowering. It was a logistical and emotional dumpster fire.
Why It Almost Never Ends Well
Let’s cut the fluff: power dynamics ruin everything.
When one person controls your schedule, your promotion, your paycheck, or your performance review, you are not on equal ground. Even if it feels consensual, balanced, or “we’re different,” biology and corporate structure disagree.
Here’s what usually happens:
1. Your achievements get discredited.
You could cure cancer and people would still whisper, “She got that raise because she’s sleeping with her boss.”
2. Your reputation takes the hit—even if he’s the one acting unprofessional.
Women especially get the fallout. We’ve all seen it.
3. You lose leverage.
How do you say no? How do you set boundaries? How do you negotiate pay with someone who saw you naked?
4. If it breaks bad… your career is the collateral damage.
You can’t silently quit when your ex is also your manager.
5. You can’t “hide” it. Ever.
Ask any workplace gossip circle. They have CIA-level intel.
Also: see The Office — Jan’s meltdown, Michael’s total delusion. Art imitates life.
If You’re Already In It… Don’t Panic (But Also… Maybe Panic)
If you genuinely care about the relationship, the smartest move is to change workplaces.
You cannot build something real while also pretending the power imbalance doesn’t exist.
There are healthy boss-employee relationships out there—sure—but those couples survive because someone switched roles, teams, or companies fast.
How to Avoid Accidentally Falling Into It
Most workplace hookups don’t start with “let’s sleep together.”
They start with:
“Want to grab a quick drink to talk about your goals?”
“You’ve been doing great work, let’s celebrate.”
“I’ll give you a ride home.”
Next thing you know, you thought you were being professional and suddenly you’re in a situation where saying no feels impossible.
Here's how to stay out of the trap:
1. Keep your radar on.
If he’s giving “extra mentorship,” recognize it for what it is.
2. Don’t hang out one-on-one without clarity.
Before you meet up, ask yourself: Is this truly work-related or is he being a little too friendly?
3. Set boundaries early.
It’s easier to keep a door closed than to slam it shut after he’s already inside the room (… metaphorically).
4. If you feel blindsided—exit.
You don’t owe him emotional caretaking. That’s his wife’s job…. JUST KIDDING. (But also… not really.)
And if you want to keep your job after being propositioned, because you’ve put in years of work and you’re not about to throw it all away, you have to shut it down strategically. You can’t bruise his ego, because bruised egos tank promotions and suddenly make “performance concerns” appear out of thin air. You need to decline in a way that keeps the boundary firm without triggering his inner toddler.
Something like: “I really value you as a mentor, and I want to keep our relationship strictly professional. If I gave the wrong impression, that wasn’t my intention.”
Translation: No—politely—so he doesn’t try to blow up your career out of embarrassment.
Got a Wild Boss Story?
If you or someone you know has been propositioned by a boss, dated a boss, rejected a boss, or watched a boss implode over an employee — CONFESS HERE.
Because if we’re going to help women become CEOs, we need to talk about the unhinged stuff that happens on the way up.
