I Accidentally Texted My Boss Instead of My Crush

Let me start by saying this: autocorrect is not your friend. Neither is fatigue, or office Wi-Fi. Especially not when all three team up to destroy your life in the span of 30 seconds.

It all began with a company team-building retreat. You know the kind — trust falls, dry sandwiches, awkward icebreakers. That’s where I met Jenna from accounting. She had freckles, perfect sarcasm, and an unhealthy addiction to iced coffee. I was hooked.

We started talking during the retreat, exchanged numbers, and the flirting began almost immediately. By week two, I was convinced she was The One. Or at least The One I’d send memes to at 2 a.m.

Anyway, fast forward to Tuesday morning — the worst day of the week. I was running on two hours of sleep, caffeine, and desperation. Jenna had sent me a flirty message the night before, and I wanted to up the ante. So I crafted a steamy text. Nothing too wild, but enough to make Shakespeare blush and autocorrect sweat.

Here’s what I meant to send:

“If we were alone in the office, I’d pin you against the copier and hit ‘Scan’ just to save the moment forever”

Cringey? Yes. But I was in the mood.

I hit send.

Seconds later, I realized something terrible.

I had sent it to “Team All — Internal Announcements” — a company-wide group chat… including my boss, the CEO, HR, and 74 coworkers I’d never even met.

Panic. Pure. Soul-crushing. Panic.

I tried to delete it. Nope. It was already “seen by 43.”

I unplugged my Wi-Fi. I threw my phone like it was radioactive.

Then my desk phone rang.

It was Debra from HR.

The Meeting

The walk to HR felt like walking toward my own funeral — if funerals involved fluorescent lighting and a very disappointed Debra holding printed screenshots.

She looked me in the eye and asked,

“Would you care to explain this… Xerox fantasy you shared with the entire company?”

I tried to speak. I failed. My mouth was a desert. My palms were a swamp.

“I-I meant to send it to someone else.”

She nodded slowly. “We hope it wasn’t meant for your manager.”

I shook my head so hard I gave myself a headache.

“No! It was meant for Jenna. From accounting.”

“Oh,” she said. “She filed a complaint.”

I died again.

The Aftermath

The next 48 hours were chaos. I became a legend — not in a good way.

• Someone printed the message and taped it to the breakroom copier.
• Someone else put a “Do Not Disturb – Scanning in Progress” sign on my desk.
• A few brave souls started calling me Xerox Romeo.

Jenna didn’t reply to my apology text. She did, however, forward it to HR. It included the words “ick,” “gross,” and “he needs help.”

Then something even weirder happened.

My boss called me in

“Listen,” he said, adjusting his glasses. “That was… wildly inappropriate. But honestly, your creativity is wasted in tech support.”

He paused.

“How would you feel about joining our marketing team? We need edgy copy like that for our Gen Z campaign.”

I blinked.

“You… want to promote me?”

“Technically, it’s a lateral move with a pay bump. But yes.”

So just like that, I was suddenly Marketing Specialist, Gen Z Engagement — responsible for writing slogans like “Scan the Vibe” and “Make Copies, Not Drama.”

The Twist

As for Jenna? Yeah, we don’t talk. Turns out she was already dating Brad from logistics, who now glares at me every time I walk past the fax machine.

But hey — I got a raise. I got a new job.

And a formal HR warning that expires in 18 months.

Totally worth it.