Office Romance Diaries: I Dated My Boss and Here’s How It Ended

Have you ever had a crush on your boss? Yeah, this one’s for you.

In this spicy edition of Office Romance Diaries, Lanre opens up about the time he got into a full-blown situationship with his boss. She’s older, fine, and definitely off-limits.

Take a seat back and enjoy.

Hey Lanre, welcome to my little corner called the Office Romance Diaries.

Lol, thank you. Let your readers know you put a gun to my head for this. But I’m here now, so let’s get messy.

Lmao! What are friends for?  Anyways, have you ever dated a co-worker before?

Yes, I have. It started as one of those youthful experiments, but it turned out to be… something else. And the plot twist is that she was my boss.

Interesting. What was your initial impression of your boss when you first started working together? What about her first caught your eye, or made you think, 'Hmm, maybe there's something more here'?

From day one, she walked into the office like she owned the place, because, well, she kind of did. She had this calm, collected energy and a way of commanding respect without saying too much. But let me be honest, she was fine. Older, yes, but fine as hell. There was something about the way she looked at me, like she already knew I'd be trouble… or maybe she was the trouble. Either way, I was hooked.

How old are we talking about here?

She was in her early 40s at the time.

Dating your boss is generally a big 'no-no' in the professional world. What made you decide to take that leap anyway? Was it a slow burn, or was there a specific moment where you both realized your feelings went beyond professional?

It started as a bit of flirtation here and there, the kind that’s subtle but charged. I once asked my guy at work if I was overthinking it, but he confirmed she spoke differently to me compared to others.  Then one evening after a late-night sprint on a project, she offered to drop me home. I got in the car, and the tension was thick. I think we both knew in that moment that something had shifted.

It wasn’t a grand romantic moment; it was messy, impulsive, and exciting. That’s what made it hard to resist.

Once you were officially together, how did the power dynamic of them being your boss play out in the relationship? Did it ever feel like work followed you home, or that your personal relationship influenced your professional tasks?

Oh, absolutely. There’s no real “clocking out” when you’re dating your boss. I’d get notes about work during dinner (yes, she invited me to her house a couple of times. Her family stays abroad), or she would ask for quick fixes while we were lying in bed. It wasn’t always bad, though. She was a workaholic, so I understood that. Sometimes it was even… hot? But yeah, there were blurred lines.

I’d be lying if I said I didn’t get special treatment. She was a sugar mummy and gave me sugar in all sense of the word.

Can you recall a specific instance where her role as your boss directly impacted your relationship, positively or negatively?

Yeah, there was this one time I messed up a client integration, and she had to publicly correct me in a meeting. It was weird because how do you separate being scolded by your boss from sleeping with your girlfriend hours later?

At what point did you start to realize things weren't working out?

Honestly, it just got tiring and riskier. She had a family abroad, and I watched her cook up lies to her husband and friends, even colleagues, just so we could do our thing. It was getting harder by the day to come up with excuses why I am stepping out of the office for lunch with her frequently, or when I got promoted at work with some higher-level colleagues, but those on my level didn’t. It was getting suspicious.

I was more scared for her than me. I had nothing to lose, but she did.

Also, while I knew what I signed up for, it got tiring being the “hidden” guy.  I couldn’t tell if she genuinely liked me or if I was just a phase. Plus, I started catching feelings, imagine a hard guy like me lol. We both knew it wasn’t a long-term thing.

What was it like going to work the day after you broke up?

Awkward as hell. I avoided her office o. But I give it to her, she was quite mature about the breakup. She went back to normal. The downside was no more perks for me. Omo, I quickly became a regular guy in the office. I don’t think I was her first rodeo, and the way she discarded me hurt.

Did you ever think about quitting your job because of it? Why or why not?

I did two months after. Not because of the breakup up though. I got another opportunity. But not seeing her every day was also a factor in taking the next job.

What's the biggest lesson you learned from all of this?

Sometimes attraction isn’t always worth the complications. Just because it feels exciting doesn’t mean it’s right. And if you’re someone’s secret, you’ll always feel replaceable.

What advice would you give someone who's thinking about dating their boss?

Think. Twice. Then think again. If it still feels worth it, then go in with your eyes wide open, not just your heart, or other parts. Because the fallout, if it happens, isn’t just emotional. It messes with your peace and focus.

Anything you'd do differently if you could go back?
Yeah. I’d probably flirt once, get the validation, and keep it pushing. Some thrills come with too high a price. And no matter how hot she was, the mess wasn’t worth the clean-up.

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