I Dumped My Boss Online

I was secretly dating my CEO online.

He had no idea that the woman he was flirting with on Facebook was sitting three cubicles away from his corner office.

Our rules were simple: no video calls, no meeting in person. It worked perfectly, until he broke his own rule and demanded to see me.

So, I dumped him.

Now, my office is a war zone. My boss's foul mood is making everyone's life a living hell, and I’m the only one who knows why.

"Take this concept draft to Alexander."

As I raise my hand to knock on his door, I’m completely panicked.

This would be our first face-to-face meeting.

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1

I was dating my CEO online.

Which would have been fine, except for two small problems.

First, meeting in person was never going to happen. And second, he had no idea the woman he was flirting with on Facebook was actually one of his own designers.

Lately, my CEO, Alexander Stone, had been in a terrible mood. A dark cloud followed him around our Seattle office, and everyone was walking on eggshells. Our daily Starbucks runs were practically cut in half.

He was working insane hours, which meant we were working insane hours. As long as he was in the office, no one in the design department dared to leave.

The result? We were all stuck until midnight, sporting dark circles so intense that even Fenty Beauty couldn't save us.

Here’s the thing: I was probably the only one who knew the real reason for his foul mood. But I couldn't tell a soul.

The big boss was "heartbroken." And unfortunately, the person who "broke his heart"… was me.

He just didn’t know it.

It all started two years ago, when my online boyfriend suddenly got pushy about meeting in real life.

We’d met on Facebook, in a group called "Seattle Singles."

He'd posted a cry for help: [Why can't I get a girlfriend?] Naturally, I clicked on it. The post read: [Male, 6'2", 180 lbs, 28, Harvard MBA. Currently a CEO at a tech company. Seven-figure salary, own an apartment and a Tesla in Seattle, but I'm average-looking. Never been in a relationship. So, what's the problem?]

The comment section was a train wreck.

[LOL, another catfish.]

[Is this guy living in a fantasy world? Harvard MBA, 28, and a CEO? Come on, this is Seattle, not some Silicon Valley soap opera.]

[We all know a guy with these stats is either gay or a controlling asshole.]

I was stressed out from a project and feeling a bit feisty. I shot back a reply: [Maybe your profile sounds like it was written by a robot. How about a picture?] Then I closed the tab and forgot about it.

A few minutes later, a private message from him popped up.

[Hi, can I send it to you privately?]

I love drama, so of course I said yes. [Sure,] I replied.

He sent the photo.

I almost spit my iced Americano all over my MacBook.

Did he just say he was average-looking? This was anything but average.

The picture was a mess. It was a dimly lit selfie, his phone obscuring half his face, taken from that universally unflattering low angle. His hair was a disaster, and he wore outdated, thick-rimmed glasses that just screamed "nerd."

But underneath all that… the man was damn handsome.

Even with the poor quality, I could make out a sharp jawline, a straight nose, and thin lips. Every feature practically screamed "hot."

And yet, something about him felt familiar.

"How can a guy this good-looking not know it?" I muttered, zooming in and out of the picture.

My inner designer couldn't help it. I fired off a few pointers: [Your personal branding needs a major overhaul. Lose the glasses or get modern frames. And the photo angle! Hold the phone higher, for God's sake. Also, stop wearing company hoodies…]

His reply was instant: [Thank you so much!]

I figured that was the end of it. But the next day, he sent new pictures, having followed all my advice. The day after, more pictures. This went on for a few days.

Just as I was about to mute him, he asked if he could hire me to "redesign" his dating profile. He offered to pay.

I’m never one to turn down a side hustle. I sent him my PayPal link. A moment later, a friend request popped up. The profile picture was all too familiar.

Wait a second. Wasn't that my CEO's LinkedIn photo?

My hand trembled as I nearly hit "accept." My heart plunged into my stomach. I scrambled to set all my work-related Facebook posts to "private."

My mind raced. Was my work email somehow linked to my personal Facebook? While I was panicking, his chat window showed he was typing for what felt like an eternity. Finally, a message appeared: [Thanks for all your help. I don't think I'll need to redesign my profile after all.]

Another message followed. [I think I've already found the person I'm interested in.]

I was completely speechless.

I compared his profile to the photo again—yep, it was him. It was definitely my company's CEO, Alexander Stone.

The coincidence was almost too much to believe. But the crucial thing was, he still didn't know it was me.

Over the next few weeks, I helped him polish his online persona, and he quickly became much more "charming." Just when I thought my little consulting gig was over, he confessed his feelings for me.

It started with a long, rambling essay. I skimmed to the end: [Actually, Emma, I think I'm falling in love with you.]

I replied with: [Um…]

Silence.

Then I tried: [Thanks for the compliment?]

He shot back instantly: [What?]

[I said I like you!]

I typed: [And I said I appreciate the thought.]

He insisted: [No, I'm serious.]

I replied: [I'm seriously appreciative.]

This was giving me a headache. Was this guy for real?

He seemed to pause, then asked: [Anyway, can you give me a chance?]

I left him on read.

That night, I couldn't sleep—a rare occurrence in the over-caffeinated city of Seattle.

From the next day on, the messages were relentless. Good morning, good night, and a running commentary of his day. "Just got to the office." "In a boring meeting." "Just had my third coffee."

So, this was how a CEO flirts.

Impressive.

I’d occasionally send a one-word reply, and he'd react like the company's stock just doubled.

I finally couldn't take it anymore and wrote: [For the love of God, please Google 'How to talk to women normally.']

Him: [Huh?]

I sighed. Perfect.

Things took a sharp turn a month later.

I was scrolling through Instagram and saw a post of a male model. I meant to share it with my best friend, but my thumb slipped and I sent it to him instead.

My comment was less than subtle: [Damn, I'd climb him like a tree.]

His reply? A single, ominous question mark.