Dating My Boss Online

Chapter 2

Me: "Is there more? Come on, send me more!"

She quickly sent over a few more videos, each one turning up the heat.

I won’t deny it. I was totally hooked. She had this way of pulling you in with her beauty.

I never imagined the girl who always seemed so calm and composed would be like this behind the scenes.

How do I describe it? It was exciting in a way I couldn’t quite explain.

Just as I was getting lost in the moment, my phone buzzed again.

She: “If you agree to be my boyfriend, I’ll send you videos like this every day. You’ll get your fill.”

Most people want four things in life: money, power, fame, and... sex.

The first three? Not interested. But the last one? Yeah, that was pretty tempting.

Me: “Alright, fine. I guess it's not impossible.”

It was just online dating, after all.

But of course, there were rules.

No going public. No profile picture changes. No video calls. No meeting in person.

She wasn’t thrilled, but she agreed.

Two years passed.

She got better at dressing up. I started eating better, and she looked flawless in every style she tried.

Just when I thought everything was locked in, she hit me with a surprise.

She: "I want to meet you. In person."

Me: "Wait, didn’t we agree to keep it online? No real-life stuff."

She sounded upset. "I know, I’m sorry… but I really want to see you."

I saw exactly where this was going.

A few days ago, I had a college reunion. Afterward, a classmate confessed to me. I turned her down, but then she sent me a bunch of creepy messages.

I posted about it, ranted, then blocked her.

She saw everything.

Now, she wanted to meet in person. She wanted to make things public. To lay her claim.

I knew why we couldn’t meet, so my answer was a firm no.

She didn’t take it well, and started pestering me for a week. Eventually, I snapped and suggested we break up.

That freaked her out. She shrank back like someone had let all the air out of her.

My phone buzzed again. For the hundredth time. I sighed, flipped it face down on the desk.

Just then, my boss, Luke Hughes, called.

Luke: “Gus, take this proposal to VP Taylor.”

It was no secret Luke had a thing for Ottilie Taylor. Normally, he’d be all over any chance to talk to her. But recently, she’d been in a bad mood, and his last attempt at comforting her ended in a public scolding. Since then, he’d been keeping his distance.

Me: “Luke, I’m a level below her. Isn’t bypassing the chain of command a little… off?”

Ottilie Taylor was my online girlfriend. I had her work contact, but we’d never talked outside of work. Plus, this proposal had been delayed forever, and Ottilie always shot it down. I knew it’d get torn apart regardless of her mood.

Luke: “Just do it, Gus. Quit overthinking it.”

...Fine.

Even though I’d seen everything online, I was still uneasy about interacting with her in person.

Especially at work, where she was known for being sharp, demanding, and a little... intimidating.

I hesitated before pulling out my phone.

Since I suggested breaking up, she’d been constantly apologizing, clearly panicking, but I hadn’t replied.

I didn’t mean the breakup talk. I was just trying to get a rise out of her. But I hadn’t checked my messages because I didn’t want to soften my stance. I didn’t want to encourage her to keep pushing.

Me: “We don’t have to break up, but can you please just be good? I can’t stand people who don’t keep their word.”

She replied instantly: “Baby, you finally replied! I’m sorry, I won’t do it again.”

Then came the crying puppy emoji.

I knocked on the door.

A beat of silence passed before I heard her voice, “Come in.”

I stepped inside, and my eyes immediately went to Ottilie Taylor’s red nose.

Had she been crying?

She noticed my gaze and quickly tried to cover it up, clearing her throat. “You here to drop off the proposal? Just leave it there, you can go.”

Her mood had definitely shifted. Normally, she would’ve already torn into me for skipping the chain of command.

But the proposal still wasn’t right, and I had to revise it.

Luke handed it back to me, saying, “Fix it.”

Looks like I was pulling another late night.

It was Friday. Most of my colleagues had already left. The only ones left were the receptionist and me.

I wasn’t sure how long the revisions would take, so I told the receptionist to head home first, promising I’d lock up when I finished.

Time passed.

Suddenly, I heard the click of the office door unlocking.

My heart skipped a beat.

It was already 10 PM. Who could be here?

I tried to calm myself, but office horror movie clichés flooded my mind. Ghosts didn’t exist, right? Still, I stayed frozen, not daring to move.

A familiar figure appeared in the doorway. When I saw her clearly, I let out a quiet sigh of relief.

It was Ottilie Taylor.

"What are you still doing here? Shouldn’t you be heading home by now?"

She seemed genuinely surprised to see me still at my desk. I bit back a curse. Of course I’m still here... all because of you.

"This proposal’s a mess. If I don’t get it finished tonight, it’s probably not going to be feasible for tomorrow. So, I thought I’d work late and fine-tune it."

"Ah, that proposal."

She paused for a moment, then, to my surprise, walked right up to my desk. "Let me explain it in more detail. It’ll be easier for you to revise that way."

I stiffened. Since we’d made up, I’d been responding to her, but now... I was stuck with the awkwardness of her presence. I’d switched over to my personal account on the computer earlier to avoid the distraction of checking my phone constantly.

What do I do now?

She took another step closer. "Go ahead, open it up. Let me take a look."

My brain was working overtime, but my hands were slow to move.

Just as I was about to make the switch, she leaned in, her voice low. "Move over, I’ll—"

"Wait!" I blurted.