Dating My Boss Online

I was dating my boss online.

Meeting in person? That was never going to happen.

He didn't even know his online girlfriend was one of his employees...

Lately, my boss had been in a bad mood. Everyone could feel it, so everyone had been extra careful. Even the usual breaks had been cut short.

The boss had been working crazy hours, and no one dared leave before him. So, our workdays had stretched to 11 PM or 12 AM, and I was starting to get dark circles under my eyes. My skin had been looking worse, too.

To be honest, I felt like I was probably the only one who knew the real reason behind his bad mood, but I couldn't tell anyone.

The boss had had his heart broken. And unfortunately, the one who broke his heart... was me.

He didn't know that, though.

It all started when my online boyfriend of two years wanted to meet up in person.

We met on social media. He had posted something asking for advice. [Why can't I find a girlfriend?]

I clicked on it, and the post said, [I'm a man, 6'2", 183 lbs, 25 years old, Ivy League graduate, with a Master's in Management and Engineering. I'm currently the vice president of a listed company, with an annual salary starting at half a million. I own a car and a house, but my looks are just average. I've never had a girlfriend. So, what's the issue?]

The comments section was full of sarcastic remarks.

[Ugh, someone's fishing for compliments.]

[Is this guy living in a dream world? Ivy League grad, just 25, and already a VP? Come on, get real. At least create a more realistic persona.]

[As we all know, only family-run businesses give young people such high positions. But most of those rich kids study abroad.]

Being in a playful mood, I commented, [Maybe it's the looks. Post a photo and let's see.]

Then I closed the app.

Not long after, I got a private message from the poster.

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

Though confused, I enjoy some drama, so I replied, [Sure.]

Then he sent me a photo.

I almost spat my coffee out.

He said he was 6'2"? I'd believe 5'0", maybe.

It was a selfie, with his face covered by his hand, and the angle made his head look huge and his body tiny. His hair was sticking up like he'd just used some kind of hair gel, and he was wearing thick black-rimmed glasses, making him look both nerdy and awkward.

But despite all that, his face was actually... fine. Even though it was partially obscured, I could tell his lips, nose, and eyes all screamed "handsome".

Still, there was something about him that seemed oddly familiar.

I mentally shouted, "There are actually guys who don't realize they're good-looking?" while zooming in and out of the photo multiple times.

With my helpful mindset, I typed out a few tips. [Your clothes and selfie skills need work. Try frameless glasses, or better yet, wear contacts. And change your shooting angle! Tilt the phone slightly, making sure the charging port leans toward you. Also, try pants that are a bit looser, like casual black ones…]

He replied, [Thank you so much.]

I didn't think much of it and moved on, but the next day, he sent me photos of his makeover, taking my advice to heart. The day after that, again. Then it went on for a few more days.

I was getting tired of it when he suddenly asked if he could add me as a friend on Facebook and offer me a thank-you gift.

If someone was offering money, I'd be crazy not to take it. So I gave him my profile link. Moments later, an account with a familiar profile picture sent me a friend request.

Wait, wasn't this my boss?

I panicked, almost accidentally accepting his friend request. My heart sank, and I quickly restricted the visibility of all the previous posts on my feed.

My brain raced, wondering if I'd somehow linked my private Facebook account to my company info. Meanwhile, he was typing for what felt like forever before sending a message. [Thanks for all the help these past few days. Here's a little something for you.]

And then, he sent me 7 thousand dollars via Meta Pay with the note, [Voluntary gift.]

I was speechless.

I compared his profile with the photo he sent me—yep, it was the same guy, and he was indeed the boss of my company.

I couldn't believe the sheer absurdity of the situation. But, after some hesitation, I accepted the money.

After all, he didn't know it was me.

The following days, I helped him tweak his photos and appearance, and soon, he was looking a lot better. But just when I thought I could quietly slip away, this guy confessed to me.

First came the long, rambling messages, which I skipped over. Then, at the end, it wrote, [Actually, there's something I've wanted to say for a long time. I have feelings for you.]

I replied with an [Um…]

The silence was deafening.

Then I sent another, [Thanks, I guess?]

He instantly wrote back, [Huh?

[I said I have feelings for you!]

I wrote, [And I said thanks!]

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

I replied, [I seriously appreciate it!]

I felt a headache coming on. Was this guy okay?

He seemed to pause for a while before asking, [Regardless, can you give me a chance to pursue you?]

I didn't reply.

That night, I couldn't sleep—something that didn't occur often.

The next day onward, he started sending me messages every day, wishing me good morning, good afternoon, and good evening, as well as updates like him heading to work, arriving at the office, and starting his work.

So, this was how he was trying to win me over.

So impressive.

I occasionally responded with short replies, and he seemed thrilled, like he'd won the lottery.

I couldn't help myself and finally replied, [Please, you should read up on how to talk to women.]

He wrote, [Huh?]

I sighed. Great.

Things took an unexpected turn a month later.

I had been browsing videos of handsome guys and, without thinking, shared one with my best friend. But I accidentally sent it to him instead.

I wrote, [Hot stuff. Wish I could just lick him.]

He replied with a question mark.