I had an online romance with my boss and then broke up with her.
Chapter 1
I’m probably the only one in the entire company who actually knows why my boss is so irritable.
She got dumped.
And the person who dumped her… was me.
She just doesn’t know that yet.
Lately, my boss has been… intense.
The first sign was when she publicly grilled one of the senior analysts over a minor formatting mistake—something she would usually wave off with a dry joke.
Then it kept happening. She started sending projects back for revisions that never used to matter, questioning timelines, pushing for higher standards, demanding explanations for anything that wasn’t airtight.
By midweek, the entire office had figured it out: she wasn’t just being thorough—she was in a bad mood, and her bar for acceptable work had shot straight into the stratosphere.
But here’s the twist: I’m probably the only one in the entire company who actually knows why she’s so irritable.
She got dumped.
And the person who dumped her… was me.
She just doesn’t know that yet.
It all goes back to a two-year online relationship.
We met on a forum after she posted a thread titled: “Why Can’t I Find a Partner?”
Curious, I clicked.
Her post read:
“Female, 5'9”, 99 pounds, 25, Ivy League grad in Management Science and Engineering. Currently a VP at a Fortune 500 company. Seven-figure annual income. Owns home and car. Gorgeous. Still single. What am I doing wrong?”
The comments section tore her to shreds.
“Obvious troll. Move along.”
“No way a 25-year-old VP. Daddy’s company?”
“At least make your lies reasonably believable.”
Amused, I replied: “Maybe it’s your looks. Why not post a picture?”
Didn’t think twice and logged off.
A few hours later, she DM’d me:
“Hi, can I send you the photo privately?”
I frowned, intrigued.
“Sure.”
A second later, a photo popped up.
I nearly sprayed coffee all over my keyboard.
Five-nine? In what universe? She looked closer to five-two.
The photo was a badly angled mirror selfie. Half her face hidden, thick black-rimmed glasses, and a vibe that screamed unintentional vintage disaster.
But her features…
Her features were stunning. She had the kind of face that would be lethal if she knew how to use it.
And weirdly, she felt familiar.
Thinking, “Wow, a genuinely gorgeous woman who has no idea what she’s working with,” I decided—purely out of charitable instinct—to help.
I zoomed in and out a few times, then typed a full critique:
“Upgrade your glasses—rimless or contacts. Avoid that angle; tilt your phone so the charging port points at you. Swap that skirt for something shorter, preferably black. And get better lighting—seriously.”
She replied: “Thank you so much!”
I thought that was the end of it.
The next day, she sent a new photo applying everything I’d said.
Then the day after.
And the day after that.
By day five, I was getting tired.
Then she asked if she could pay me for “consultation services” and requested my personal messaging info.
Money is money, so I gave her my private account.
A moment later, a familiar profile picture popped up.
It was my boss.
I froze.
My thumb slipped and hit accept before my brain caught up.
Instant panic. I switched my settings to “chat only” and prayed she wouldn’t connect the dots.
She messaged:
“Thank you for everything. Here’s a small gift.”
Then sent me $5,000 with the note: “No conditions.”
I stared at the screen, stunned.
I checked her profile picture again. Checked the forum selfies.
No mistake.
My mysterious online crush was my real-life boss.
“Well, hell,” I thought, accepting the transfer. “At least she doesn’t know it’s me.”
From then on, I kept helping her polish her style. She learned fast, and soon she was walking around radiating confidence.
And just when I was preparing to quietly bow out of her life, she blindsided me.
She confessed.
Her message was long and dramatic—a digital love letter. I skimmed until the final line:
“I’ve been wanting to say this for a long time… I like you.”
I froze.
“Thanks,” I typed.
“What?” she replied.
“I appreciate it!”
“I’m serious,” she insisted. “I really like you.”
“And I really appreciate it!”
Silence. Then:
“Can I at least try to pursue you?”
I didn’t answer.
The next morning she began sending good-morning messages. Then good-afternoons. Then good-nights.
Updates every hour like we were already dating:
“I’m heading to work.”
“I just arrived.”
“Going into a meeting.”
Her persistence was… something.
I responded halfheartedly. That only encouraged her more.
A month later, things took a sharp turn.
I was scrolling through social media, admiring models, and accidentally shared one with her instead of a buddy.
“God, she’s gorgeous. I’d lick the screen,” I wrote. “Here’s the video.”
She replied instantly:
“???”