Dating Your Co-Worker is Probably a Bad Idea

I don't care how many fan-videos you've made over Jim Halpert and Pam Beesly; these days, I'm always going to give dating co-workers a giant side-eye.

Nov 12, 2012 at 10:00am | Leave a comment

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I don't have any photos of myself as a barista, so here's a horribly unflattering photo of myself in April at my current job. WHO WOULDN'T WANT TO DATE THAT

For 20-mumble in This Modern Age, a question that often seems to arise is “How the hell do you date like a normal?” For those of us (me) weaned on stories about people meeting-cute over a steaming cup of alien gore or having to rescue each other from sentient Espresso Machines of Doom, it’s easy to fall into despair.  

In college, I got complacent. I was surrounded by literally thousands of young, relatively attractive, decently smart dudes and ladies with whom I had at least one thing in common. If I’d really wanted to, I probably could have struck up the kind of relationship that included Saturday morning cuddles and sending each other photos of particularly impressive bowel movements. 

Of course, Kate of 2007-2011 was much like Kate of the Present: that is, far too busy stuffing tortilla chips into her gob and writing stories about werewolves to bother sustaining any serious romantic relationship where she’s someone’s primary. 

One thing I do miss, though, is the comfort of the potential. No, I probably wasn’t going to serious-date the President of the Longboard Society or the girl in my Chaucer class with the head of curly hair and the knack for sussing out Middle English words. But there was something soothing about propping my chin on my hand and idly wondering what our kids would look like.

For me, romantically speaking, college was a web of delicate possibilities, each doofy shared smile or chance encounter at the local bagel place a tug on one of the strings. It’s hard to replicate that kind of tiny, easy thrill when most of one’s social encounters take place on public transit or in bars.

My friends often bemoan this same point, and I know it’s why a lot of people take their dating talents online. There is one possibility that my bros keep bringing up, though, as a way to meet people who almost certainly aren’t serial killers and with whom you have more in common than just, “You’re mildly drunk and so am I.” Dating a co-worker. 

At my current Big Old Adult Job, there aren’t any actual policies that would prevent me from dating any colleagues (I think). However, it’s very difficult for me to wrap my mind around seeing anyone I work with in a light that isn’t strictly platonic, maybe with the very occasional side of, “It’s your bachelorette party so we can make out on this pool table a little bit.” For some reason, the very idea of taking any of my awesome work-friends out for a sexy date just seems kind of improper.

This, admittedly, may be a residual emotion. The one time I did kind of date a co-worker, it was probably against some sort of policy for us to be having awesome naked times in the off-hours. Of course, the rules for baristas at the very shitty, much-beloved Seattle’s Best knockoff that lived in our school’s library were tenuous at best. 

It wasn’t uncommon, for example, to see employees methodically punching 9 holes out of the “Buy ten, get one free!” cards that lived by our registers and handing them to their friends. I would frequently cart home literal trash bags full of bagels from my closing shift and store them in our house freezer for whenever things got dire in the nutrition department. I also used to make myself “drinks for the road” that consisted of seven shots of espresso, some soy chai, and four pumps of peppermint syrup. Like I said, things were a little lax.

That said, Diana was also technically my boss. And by technically, I mean she was actually my boss. She was only a class year ahead of me, so it was tough to be suitably cowed by her, but she had hired me and was in charge of any disciplinary action that had to be taken against me. Which, in our case, was mostly the sexy kind of discipline. Wink.

At first, half-dating Diana while we worked together was awesome. Diana is smart and bubbly in addition to being drop-dead hot, so even before we’d started making out all the time, we’d gotten along great -- she’d let me blast Fall Out Boy during our shifts, and she never yelled at me when I fucked up lattes (which was often). 

And after we did start sleeping together, there was something delicious about feeling her watch me as I scrubbed the espresso machine, about hooking my chin over her shoulder as she counted money from the register. She’d tweaked the schedule so we could close the shop together all the time, and I remember feeling a warm contentment pool in my belly as we cleaned in near-silence, knowing it was only a 10-minute walk to my place after we’d locked the cafe doors.

This is starting to sound kind of porny, but that’s what happens when you date a co-worker: all those normal, cute relationship things start taking on this weird weight. Di was my boss, so we had to keep it a secret in our case (spoiler: it was not actually a secret). But even when co-workers have hit on me at other jobs, my first response is always to give the sentiment more significance than it probably has. When I worked for the California Department of Water Resources as a teen, I used to physically hide from a dude just because he’d taken me out to a supremely awkward lunch one time. 

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I was also a caving instructor in college. Wonder why none of THOSE co-workers ever wanted to date me.

Just like dating a housemate, dating a co-worker blurs boundaries that you didn’t even know existed. When Diana and I eventually got cranky with each other, it was usually because I felt like she was “smothering me,” when in reality, she was just working the same crappy/awesome coffee-slinging schedule I was. Meanwhile, she’d rant to my friends about how I acted like an unfeeling bitch when I did see her, which, point Diana, but I was also trying to focus on my job. So unfair. 

It’s hard, because so many of us define ourselves by our professions these days. It feels weird to share that self-label with someone you’re dating, even if they came by it on their own terms. I’m a compartmentalizer: when things are precious to me, I like to curl around them for a little while, to not share them with anyone else. Dating a co-worker makes that damn near impossible.

Plus, if you’re a little anxiety-machine like me, it’s easy to play the What if The Worst Happens Game and envision your relationship crashing and burning six months down the road. I like to stay friends with my exes, but everybody needs a little space. And when you’re forced to spend quality after-hours Excel document-generating time with the person who just broke your heart, suddenly that quivery proximity gets a lot less sweep-the-papers-off-the-desk romantic. 

I really liked dating Diana. But I do sometimes wonder what would have happened if we hadn’t worked together, if she'd decided to hire someone who had actually worked a food service job before in their entire life instead of the almost-senior with the cute smile (her words, not mine). If instead, we'd met because we shared mutual friends, or because -- god forbid -- I actually slipped her my number as I ordered an Americano.

The space probably would have made us a lot less miserable toward the end of things, or at least forced us to communicate in ways more substantive than grunting and flinging empty coffee cups at each other. She and I are still friends, but it involved a hell of a lot of heartache there for a little while.

As adorable as I (and the rest of everyone in America with a working soul) thought Jim and Pam were on "The Office," my guess is that most couples that begin in the workplace end up closer in spirit to me and Diana. Sure, some people can channel their inner Leslie Knope and Ben Wyatt, but my guess is that most office relationships involve a lot of HR-wrangling and passive-aggressive milk steaming. Or maybe just the ones with commitment-phobic jerkwad baristas like me.

Kate is deeply committed to her relationship with social media at @katchatters