Whisper: In Love With My Boss

With that title, you have thought I’m some millennial young girl drooling after a millionaire man. Truth cannot be further than that.

I won’t disclose my age but I have been working with this man close to 10 years. Heck, my past relationships haven’t even lasted more than 5 years. For the sake of anonymity, let’s name him Ryan after my favourite actor, Ryan Gosling.

I’m Ryan’s personal assistant. It didn’t start out that way. I was working in the same sales department as Ryan and as his career soar, he jumped from a salesperson to a sales manager and now a sales director.

After the second year of working alongside him, he decided to resign and brought together with him a number of sales folks, I included.

Slowly, I begin to work with him on major projects and we love our working chemistry together. He requested that I moved on with him as his personal assistant when he hopped to a much bigger company in the same industry.

By then, I was madly and secretly in love with him and I jumped at the opportunity to be close to him.

We work so well together. Our ideas just clicked and we always ended up conquering the most difficult projects with impossible deadlines. All our colleagues admire our close working relationship.

Even our clients mentioned that we are like Bonnie and Clyde. Our biggest clients trust my word when I said I speak on behalf of Ryan. There were plenty of late nights and business trips together and that just fuels our bond.

I begin to take note of his likes and dislikes. I know his favourite colour is blue so a lot of my work clothes are in different shades of blue. I know how he likes his coffee and I make sure that he gets that twice a day. I know that he gets riled up before every meeting and how he hates his mother sending him flowers at work on his birthdays.

Oh, how his eyes twinkled whenever we closed a big client. Or how his eyebags will show if he had a sleepless night. I even know the reason behind the sleepless night. That’s how much I adore him.

I know he doesn’t approve relationships at work and often make comments about it.

So I keep my distance. Not brave enough to let him know how I really feel. I tried to move on and forget him romantically.

Oh, how I tried.

I have several relationships outside work and I keep finding myself secretly comparing others to him. Nobody seems to even come close. I know I’m doomed. Instead of destroying more men’s heart, I choose to be single for the past year.

Ryan had his portion of failed relationships as well. I’ve seen women come and go. As his personal assistant, one of my jobs is to set up dates and send flowers to ladies. All his ladies are gorgeous and smart. I’m nowhere near that kind of standards. I do not belittle myself but I am also realistic.

My best friend knows about my crush on Ryan and thinks that I’m wasting my time. I can’t seem to walk away. By the way, I love what I do and working with Ryan is a perk. Yeah, unrequited love can be lonesome and heart do ache. I shudder to think of what will happen if I confess.

Maybe I’ll let him know my feelings one day. Just not today. Not this week. And not this year.

Can’t get enough of work secrets? Or do you have one of your own?

Check out these Whisper stories:

Whisper: I’m Pretending To Be Who I Am

Whisper: I’m engaged to my boss’s daughter but I don’t even love her

Whisper: I’m In Love With My Student

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12 Comments Add yours

  1. Kat says:

    This is like a movie, Kally!!! I wouldn’t know what to do myself if I were in her shoes. I think I wouldn’t want to confess BUT it would hurt so much.


  2. Paul says:

    I remember a fellow department chairperson telling me, “Your office manager is your other wife.”

    Liked by 1 person

  3. Unrequited love can be so painful to the heart — but rejection could bring the whole house of cards crashing down. Touch situation.


  4. Ankur Mithal says:

    There was a time when personal assistants at work, generally women, to senior folks in the company, usually men, were referred to as ‘office wives’.

    Liked by 1 person

    1. Kally says:

      Really? That’s something new. I haven’t heard before.


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