How I Ended Up Dating My Boss


It started out with a note. I was always very adamant about not wasting paper. In fact, I spent most of my days frequently memorizing messages that were meant for management rather than scribbling it on our expensive Post-Its just to conserve the company money. Sometimes the messages were jumbled, and my “weakness” of being scatterbrained started to show despite the fact that I worked in an office position. You were the more organized type, the kind who will let his emotions pile up before the dishes do and won’t let even a slightly wrinkled shirt make acquaintance with the sunlight past your front door.

You used to make fun of me for how messy I was. You insisted it would be fine to just continue using the Post-Its for their intended purpose and told me not to worry about waste because the company would pay for more. I blush every time this happens but you always follow up with how impressed you are with my memory and how sweet it is that I am concerned with helping to conserve the environment.

I have never been a perfectionist but something about you made me want to always try harder. Every time you and the big BIG boss delivered my quarterly review I anticipated your comments more than his.

Work was always something to look forward to whenever you were there. Even on the busiest and most migraine-inducing days you always found the time to come up to the desk and crack a few jokes with me. I discover that we have a LOT in common beyond representing the same brand name on our tax forms and Facebook profiles. We discuss music, our families, morals, and every item on the forbidden list of "things to not be talked about in the workplace." Our daily banter becomes a part of my routine, and I focus intently on quickly finishing all of my banal, clerical tasks early in my shifts to give myself more time to bullshit with you.

But one day I happened to catch a glimpse of you paying attention to me. And I mean REALLY paying attention. It wasn’t even necessarily the first time I dolled myself up but on some random afternoon. I was walking toward the back room when you stopped me in the hall between the kitchen and dining room. But this time it wasn’t to set the night’s game plan, but to tell me how pleasant my perfume smelled. A sly first move, I must say. However at the time whenever I received a compliment from you my face muscles tightened to restrain the burst of joy that would shine through my smile.

I kept denying that there were feelings because I knew how wrong it was. You were the one in charge of my paycheck and whether or not I could continue working here. But I couldn’t deny that there was something about you I was inextricably drawn to.

Maybe it’s your striking presence every time you walk in a room. Your body language commands attention without begging for it, which is why people immediately turn to you for questions and advice. At six-foot-five with big, broad shoulders and a brand new suit, you already look like someone’s boss. But you’re not the kind interested in kicking his feet up in the office and tally-charting how many folks you’ve fired or even obsessing over the day’s sales. It’s not your status that attracts me. You have power but you never abuse it. You have a deep compassion and concern for the well-being of your employees (and the greater public) and make personal sacrifices every day to ensure the happiness of others. You never took yourself too seriously, and yet when we had our side conversations and you eagerly discussed current events with me, I could tell you were being very sincere. You never make me feel like your subordinate. Every time we’re near each other I feel like I’m talking with an equal. My equal. I try restraining my feelings and silencing them once and for all. This is completely inappropriate and I will end up fired if I start to act overly flirtatious. But would it have been worth it? I start to imagine the prospect of dating you with me no longer working there. No. That’s an impossible fantasy, and besides, you probably don’t like me anyway.

Why couldn’t I fall for another staff member that wasn’t a manager?

But one day my actions started to be reciprocated. On a slow afternoon you slip me a memo underneath my hand. The inside reveals a song I’ve heard on some indie blog recently, and I gaze at you with admiration for your ability to stay current despite some people thinking you’re too old for “the scene.” I’m grateful for your kindness in recommending a new tune for me to tap during my lunch break. I’m even more ecstatic when you hand me a pen and post it with a grin as you utter the words “your turn.”

The mere idea of any of our exchanges going beyond the number of bookings we had for Saturday or how short we were on staff pens was inconceivable. Sure, I joked with you more than I did with any other manager, and our conversations flowed with a comforting ease, but our relationship was professional. Nothing more. And even if I wanted something more, let’s be honest—it was impossible. Even in those moments where I would daydream of you and I closing shop and your arm caressing mine I felt tortured. I remember being in high school and crushing on hot teachers, and even drooling over the hot teacher’s assistants in university but there was some flavor about you that I couldn’t resist latching onto.

My roommate insisted that it was my subconscious simply hinging on the fantasy of sleeping with an older, financially stable higher-up in the workplace. She criticizes my careless willingness to take risks and reminds me of how precarious my position is in the company. Why not hook up and find someone at the local crafted cocktail spot instead? Besides, you don’t even know if he’d actually go for it. It puts his job at risk too, you know.

I disregard caring roommate’s advice and decide to continue this courtship. Out in the parking garage, near the cash registers, behind the ATM, in the foyer, a midst the action of the kitchen. Did we not think anyone would notice? I question that this probably isn’t what I think it is (or rather, want it to be). I’m not even sure if this has any meaning at all and wonder if this is more than a schoolgirl crush. Your Post-Its populate my nightstand. At work I struggle to keep a straight face because when you’re around I can’t help but smile.

I notice that you suffer from similar reflexes when in my presence as well.

There is an unspoken code that guides all of our interactions with each other. And although neither of us has verbally or physically acknowledged this subtle connection, whenever I catch your bright, inspiring blue eyes locking on mine from all the way across the foyer I know something’s there.

One day I summon the courage to speak forward (but casually still manage to be indirect about it) to you about a possible invitation outside of work. We chat with the wonderfully secret Facebook Message platform to discuss our rendezvous and the possibilities of heading to a concert. You use phrases like “let’s kick it” to lessen the evident romantic undertones of our plans. I find it endearing because you’re the one who insists we break rules and hang out at all.

I arrive at your home biting my lip in nervousness. But really I do it in hopes to prevent my massive, dorky smile from overpowering my visage and adding to the awkwardness of us hanging out beyond the walls of our workspace. You open the door and I can tell you’re nervous, too. I’m impressed that you still find a way to dress in full button-downs and nice slacks even outside of work. We both joke about how funny it would be if the big boss drove by right now and happened to catch us hanging out. The air of “danger” surrounding this makes this quiet encounter much more exciting, and I can tell you’re as thrilled about it as I am.

You welcome me with a glass of red wine and tour me through your home. I can’t believe that I’m actually here and this is really happening right now.

I survey your common areas because my hunger to know every detail grows with every step I take. The current set-up of contrasts immensely with the methodical and controlled image you present at work. Your pots and pans haphazardly cover your countertops where you spend a great deal of time cooking and not cleaning. (Culinary school grads hate that part of the process in the same way lit grads hate assigned readings.) The room is littered with DVDs and books and your refrigerator boasts more beer than actual food. You explain that you’re in the middle of a move, but I interrupt to tell you that I admire this side of you.

You’re not perfect, but you are shamelessly a human. In this moment you’re not my boss, but a friend. And I am not put off by the mess despite your insistent apologies, but rather, more excited to spend time in a space that you could enjoy without being sneaky about it. For the first time, we enjoy each other’s full company, instead of those little moments with each other at THE company.

It isn’t until a few drinks later that we’re both indulgent in each other’s laughter and drunk from all of the stories and double IPAs that I see something through the archway into your living room. It’s a coffee table covered with pamphlets and the lease for your new place. But amidst the piles of documents there is a small stash neatly folded and packed like some kind of secret treasure to be protected from possible coffee spills or being lost during a move. I recognize this reserve immediately:

It’s the stack of notes I’d written to you.

Every single one.

And then I no longer needed to question if this had any meaning or purpose…I just knew.

Months later I wake up next to you (with a new job, of course) and I can’t help but laugh knowing that I would have ever let a possible promotion prevent me from feeling as happy as I do now.