Last week was Fleet Week here in NYC, and thousands of sailors in their crisp summer whites flooded my humble city under the warm and breezy blanket of late spring.

The air was teeming with nostalgic romance.

It’s my favorite week to be outside, breathing in the streets of New York. ❤️

My husband is a Navy veteran

He’s also a proud member of the New York Council Navy League, so we found ourselves at a reception at the swanky New York Athletic Club on Friday night.

We cozied up to a table with another civilian couple, and began the awkwardly pleasant “getting to know you” conversation.

When my husband asked how they met, the man replied “At work — she was my boss. Nobody at the office could believe it when we started dating.”

That had the potential to be a sticky situation. 

Even their coworkers knew it. 🤷

But against the odds, we learned that these two lovebirds had been happily married for 24 years, with two successful adult children. 

To top it off, they still work together — but instead of the small tech startup where their love initially blossomed, they’re employed by a behemoth investment bank (rhymes with Schmorgan Schtanley).

This got me thinking…

👉 My parents met at work.

👉 I met my ex husband at work.

👉 And I consider myself personally responsible for no less than 3 marriages because I hired folks who ended up together.

But more often than not, workplace romances (and attempted romances) go horrifyingly awry.

That’s why the idea of finding dates at work, or even in a professional environment like a networking event or a conference, fills most folks with dread.

How does it go…

Don’t shit where you eat— right?

Well, it depends.

Let’s review the good, the bad, and the ugly. 👇️ 

The good ❤️

Michelle Robinson was a first year associate at the Chicago office of the prestigious Sidley & Austin law firm.

And she was (smartly) determined not to shit where she ate.

Having recently graduated from Harvard Law School, and being one of very few black female lawyers in the firm, she was steadfastly focused on her career.

She was going places — and no one was going to distract her.

That is, until a summer associate she was assigned to mentor showed up to her office—

Late. 🙄

Michelle was not impressed.

She was even less impressed when he lit up a smoke later that day. 🤮

But in the weeks that followed, she found herself charmingly amused by the tall, cerebral, second-year law student under her charge. And it was becoming clear to her that he was interested in more than just an experienced mentor at the firm.

“Whether I was going to admit it or not, something between us had started to change,” Michelle wrote. 

But she was determined to keep her life “tidy and forward focused—free from any drama”.

So when he casually asked her out one day, his baritone voice and goofy grin melting her carefully guarded heart, she declined. 

But she didn’t decline in an assertive “I can’t believe you just went there, leave me the f*ck alone” way. 

She declined in a flattered, flirty, and (dare I say?) inviting way.

Y’all — this is why workplace romances are so tricky.

He shot his shot, and she declined. On paper, it would appear that any further advances on his part wander into “hostile workplace” territory.

But bravely (or stupidly), he persisted.

And one afternoon, following a firm barbecue, with their hands wrapped around ice cream cones melting in the summer Chicago sun, he laid a smooch on her.

And they’ve been madly in love ever since. ❤️

Clearly this one worked out, but it could have been very different. Young Barack picked up on cues, and fluently read between the lines.

This skill enabled him to carry out a workplace courtship that would go on to make history.

And I’m not gonna lie — I melted a little when he shot me the same goofy grin that won over Michelle all those years ago…

The bad 😣

Having a McRelationship at work can lead to a McFiring — and a whole lotta McF*ckery.

Back in 2019, Steve Easterbrook was the global CEO of McDonalds — a Dow Jones top 30 company on a huge resurgence.

• He was single.

• He was rich.

• He was (kinda) handsome.

• And he could be considered a catch to some. 🤷

But CEOs of massive corporations probably shouldn’t be wading in the dating pool of their subordinates.

Steve was ousted by the Board of Directors when they discovered a consensual relationship he was having with an employee.

Ouch. Poor Steve. 😣

He did it in the name of love, but it was against the rules.

And while the Board knew they needed to fire him, they opted to do so “without cause”, which meant he walked away from that job with a $40 million severance package.

Break the rules and get $40 mil? Sign me up!

• He was still single.

• He was still rich.

• He was still (kinda) handsome.

Sounds like he got a pretty great deal. 🤷

Except a few years later when an internal investigation revealed that he actually had several sexual relationships with subordinates, which included exchanging explicit photos and videos—

On his work email. 🤦

In addition to that little titillating piece of gossip, he also awarded one of these ladies a stock grant worth hundreds of thousands of dollars in the midst of their relationship.

And he had kept all of this from the McBoard.

So they sued him. They wanted their $40 million back.

The S.E.C. wrote their own love letter, fining Steve $400k and barring him from serving as a public company executive for five years.

How romantic. ❤️

For a guy whose leadership sent McDonald’s stock soaring during his tenure as CEO, he sure made some pretty shitty decisions on how to conduct his love life.

And finally — the ugly 🤢

A few months ago, I was cheerfully chatting at a professional (seeming) happy hour hosted by a venue next door to the Fox Business studio here in NYC.

One of the folks I met was a middle-aged investor and Fox Business contributor we’ll call Bob. We chatted about alternative investment strategies and our respective families (he was married with 3 kids).

He said that he found my insights super compelling, and would love to tell his Fox producer about me. He even pitched me a podcast idea.

• BOB: "Let's stay in touch."

• ME: "Sure, let's connect on LinkedIn."

• BOB: "I'm not really on LinkedIn much, but if you're ok with it, we should exchange phone numbers."

• ME (jokingly): "Sure, I can always just block you if I need to."

• BOB: “You’ve blocked people before?”

• ME: “Oh yeah, it’s the most freeing feeling in the world.”

I recited my number as he typed it into his phone and sent me a text with his name on it so I’d have his.

I moved on, and as I was walking home, I received this gem. 👇

Ick. 🤢

Shudder. 😣

Y’all — I’m pushing 40, chubby as f*ck, and sincerely thought the days of inappropriate men using the tiniest sliver of perceived power they have to “advance my career” were behind me.

But what’s most baffling is the unabated risk this otherwise intelligent guy (and somewhat public figure) took when he decided to hit on a random married woman.

👉 I could easily ruin his life. 

👉 I could send his wife this screen shot. 

👉 I could complain to Fox about his behavior.

But instead, I’ll just share this story with you as a cautionary tale.

So what’s the lesson here?

It all boils down to one thing — good judgment.

Sorry, not just good judgment…

Excellent judgment. Impeccable judgment. Superior judgment.

Many healthy relationships have been born out of workplace romances. Heck, I wouldn’t be alive today if my parents hadn’t gotten cozy at work.

Just use your 🧠.

Not your 🍆. 

😉

Cheers! 🍻 

-Kristin