My office crush was twice my age, and three times my senior.

Besides the fact that we worked together, that he had a family, and he was old enough to be my father… why shouldn’t I be obsessed with him?

LittleWrenWrites
The Bigger Picture
7 min readFeb 19, 2024

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I’m at a work conference when I see James walk towards me. James used to be in the creative industry- for his writing- and is now a corporate businessman and a married man twice my age. He’s also the subject of what I’ve hazily defined to myself as a “dad crush”. It started off as admiration- I lapped up the fact that he was the only person with a remotely creative past in my clinical, insular workplace. I recall a sense of curiosity, propelled by transactional motives. I was hoping to impress him enough to get a referral, or at the very least, advice. And then my feelings got more complicated.

When I’d just joined the company, I was assigned to him as a hapless new starter in need of help. We’d find ourselves on conference calls often, as he guided me through lodging my timesheets through the finicky web portal, and introduced me to the business. As we’d sit and wait for the portal to load, I would sweep my gaze down the smooth slope of his nose, then trace his profile back up to the tousled hair falling across his forehead.

I’m not sure how long it took me to become cognizant of my feelings for him. I think my brain repressed even the faintest whiff of attraction because I knew how taboo it was. Compounding on the married colleague factor, the age gap factor felt like enough to assign my budding crush to somewhere between gossip fodder, to straight up scandalous. But, as with all things one tries to repress, thoughts inevitably sneak up to the surface. I found myself paying particular interest to anything with his name on it, and looking forward to our regular meetings. I was suddenly conscious of how I looked in our one-on-one calls, preening my hair in the tiny viewfinder on my screen before I joined on video. All these textbook signs of a crush, and I was showing them for… a senior, married colleague? I hadn’t experienced anything like this before, and it unsettled me. Straight-edged and conventional, my sphere of attraction had always been very typical. My history of crushes and relationships had always been age, occupation and marital status appropriate. It was dinned into me as a child growing up in a strict, conservative household: don’t step outside the lines. Do what you’re meant to do. Once, I developed feelings for another woman, a good friend of mine, and even then, I was too scared to act on that part of myself. So the apparent illicitness of this took me by surprise. It scared me too.

Meeting James during a work trip only confirmed my attraction. With hair just as tousled as it was on camera, he was even more handsome in real life. After skipping lunch to finish off a task, we broke off from the team in the late afternoon to find somewhere to eat, starving and in need of food. We were joined by some newly hired interns, who were excited to talk to James about his creative past as well. I sat quietly, contentedly with them, eating my salad as they chatted. I remember staring idly at the silver necklace around his neck, as his Adam’s apple lilted in time with his speech. When we moved on to other topics and he mentioned his children, I watched his eyes, tinged with pride, and felt like a criminal. I didn’t want anything to jeopardize my working relationship with this man, let alone his family. But my thoughts felt dangerous, like their very existence made me complicit.

But something about being in a new city, walking side by side with this man, having his entire, corporeal presence in front of me, made my heart thrum. Walking in the sun, I felt light, translucent. The warm air rustled past my limbs. It made me feel like anything was possible. I glanced up at the skyscrapers and imagined myself alone in a room with him, and the hairs on my neck stood up on end. The clandestine illicitness of the thought tasted like cotton candy. It made me feel like I could do anything, kiss anyone, run into the sweaty, sticky embrace of the city and live a thousand lives, each one more daring than the last. It was like some part of me had been sitting in a darkroom, developing, and someone had flung open a window to bright blue sky.

Now, at this conference, James approaches me. He greets me, and we chat briefly about the agenda for the day- and right before he walks off, he adds, “you look nice, by the way”. He looks at me warmly, piercingly, and something indescribable flutters within me. His comment stays in my mind for the rest of the day. Is it possible that my attraction isn’t completely one-sided? His words make me feel coyly pleased, but part of me also feels the subtle transgression of an older man saying that to his much younger, female colleague. I have felt the discomfort of older male colleagues commenting on my appearance before, and have feigned ignorance of their lingering glances at my chest, my waist, my hips. His comment also makes me feel a blip of discomfort- but there’s a worrying lack of disgust, a smug satisfaction at his words that tells me that it’s different with him. I feel like such a hypocrite. I’m even more conflicted when he invites me to join him for a day -just him- for a client briefing, later that week before I head back home. I feel like I should say no. But the promise of that one summer day, many months ago, calls to me.

And in the end I go with him. We walk side by side through bustling crowds, and are forced close enough on a packed elevator that I can see the flecks in his eyes. We meet the client, we talk about future projects, and a couple times when we lock eyes, it feels like our gaze lingers. But nothing happens. Even as we’re walking back in the languid, rosy heat of the city streets, things stay entirely professional, and our conversation, and our boundaries, never stray past common niceties. When we get back, he has to leave- he’s got another client to see- and I don’t even get the chance to say goodbye to him before I have to go to the airport.

When we get back, he has to leave- he’s got another client to see- and I don’t even get the chance to say goodbye to him before I have to go to the airport.

Sitting at the airport terminal, I open my laptop, intending to squeeze one last hour of work in. But I can’t concentrate. I keep replaying his greeting comment to me, his gaze, the feeling in my stomach. Distracted, and craving solitude, I go to the bathroom and lock myself in a cubicle, trying to sift through my thoughts. I take out my phone and bring up Google. I need to know that others like me have had this experience, this illicit feeling of attraction to someone you really shouldn’t be interested in.

I find many posts online, all describing the same predicament. I’m a young woman, and there’s an older man at my work who I’ve found myself attracted to. He goes unnoticed at first, sometimes even un-liked, until a budding attraction blooms. Sometimes he has a family, sometimes he doesn’t. Sometimes, the writer wants to pursue something with him, a real relationship, or a fling — sometimes not. They all want to know the same thing. What do I do? Am I crazy? When I go to the comments, they’re just as varied. Some, scorning and condescending, write her off as a young slut, stressing how immaturity just leads to regret. They paint the image of the young vixen, the promiscuous homewrecker who needs to be stopped before she destroys another happy family. Others, cautiously, encourage a rational approach. Think this through, they say. Even if you were to find out his feelings are reciprocal, what would you do? What happens if it doesn’t work out? If you’re sure you like this man, and he’s actually single, then maybe you can try and see how it goes. But be sure it’s what you want. The first type of comment makes me bristle. The second type of comment makes me sober.

Over the next few days, I ask myself why I’ve developed an infatuation with this man. Standing in front of the mirror, I imagine him behind me, his hands on my waist. When the image crystalizes and I picture the skin of his hands, leathery, rough and old, I suddenly feel an overwhelming repulsion. I don’t think I want to be with him. I just like him. I like the fact that he has his life together, that he has the maturity that comes with two children, a marriage, a mortgage, and a tried and tested career. I like him because I envy him, because I want to have worked as the starving artist, struck out my own path and endured the pain and struggle- instead of withering away here because I’m scared of trying and failing. I like his sense of self-assuredness, his confidence, his hard-won contentedness. Maybe I don’t actually have a crush on him, and it’s all just admiration and envy. That being said, I have known the flutter in my stomach for him, the tunnel vision that goes past admiration to infatuation.

But in the end, maybe I don’t need to dissect every little part of my longing like this, like trying to pin down torn butterfly wings to make a perfect specimen. Maybe it’s enough just to feel, and think, and let this teach me something about myself. I don’t think I will ever let my story with James go beyond innocent, puppy-eyed pining. I’ve accepted that our cordial pleasantries are all our interactions will ever be. That being said, I have learnt to let my feelings teach me about the far-flung possibilities of what I want, and who I might have capacity to love. I am trying to let the infinite possibilities of those languid city days into my reality, one at a time.

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LittleWrenWrites
The Bigger Picture

A twenty-something young woman, chirping away on life, loneliness and love (or the absence thereof)