How to Sleep With a Co-Worker and Not Completely Destroy Your Career

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Offices are painfully boring places and they harbor more shattered expectations than a Britney Spears concert arena. When you pack that many barren cubicle walls and defeated spirits into a shared space, rumors spread faster than a crown fire in Yellowstone National Park. If done in front of the gossiping wenches in marketing, a playful arm graze in the break room could turn into a story about the two of you going full-blown pile-driver position on the boss’s desk. In summation, flirt discreetly. 

The best way to secure an office hookup is to work at a PR agency, accounting firm, or in the event planning business. Those places are mostly women and, like, a team of goonish IT guys. In other words, you’ll be the de facto work boo without much effort, and the intrinsic competition amongst females in the office will strengthen your perceived worth, even if you're not worthy of the praise.

Getting it in with a co-worker might seem like a good idea during an especially salacious happy hour, but the indignity of this particular romp cannot be remedied with a hot shower and McDonald’s breakfast. You’re going to have to look that person in the face, five days a week. The intra-office one-night stand is not for rookies, so game responsibly.

Think about all of the people you’ve slept with and where your relationships with those people are today. OK. Now, imagine having an ex or past romp in charge of your schedule, delegating work, and rating your performance. If you’ve followed through with our supposition, this is the part of the hypothetical where you flog yourself into unconsciousness with a company-issued keyboard. You’re not Monica Lewinsky. Unless you’re committed to archiving soiled pieces of clothing, boofing your boss is more likely to result in an employee transfer than a book deal.   

The office party is a catalyst for questionable life choices and marital affairs, so keep your head amidst the company-sponsored revelry. You might plan on casually chatting with a hot girl from sales and (fingers crossed) landing a subsequent dinner date. But, if you get too drunk, you could just as easily end up making out with a Cabernet-dependent mother of three in a bathroom stall. No career woman is going to let you sully a pantsuit she bought a Dillard’s if you reek of Fireball shots and neck sweat. Don’t let your crush, secret lover, or boss catch you slipping.

In the vain of keeping things discreet, don’t roll into the office on a tandem bicycle or spend lunch sharing a Caprese salad with boo in the corporate plaza courtyard. As a bastion of misery, the workplace is a horrible place to vaunt happiness. And, as previously discussed, the consequences of intra-office romance can be countless and severe. Keep the work snakes lost in the grass.  

The corporate setting is where trivial gaffes go to get blown entirely out of proportion. You know how angry that chick from accounting gets when someone accidentally hits “reply all” on an email when a direct response would have been sufficient? Well, multiply that violent rage by the square root of Mel Gibson’s furrowed brow for a numerical representation of HR’s vindictive wrath.

Realistically, you won’t do a cost-benefit analysis between having sex with a co-worker and losing your job, particularly while making out with Susie from finance in the backseat of a cab. But, the workplace can be a painfully arduous and harsh place to mix business and O-faces.

It’s hard to wiggle out of plans and ignore texts when you and the person you’re trying to flake into disinterest share the same printer. If you’re full-blown dating a co-worker, then you’re going to have to be a grownup with the breakup. We just hope you’re ready.

It’s fun to break rules and, while at the office, you’re impervious to the watchful eye of your girlfriend. Furthermore, the artificial interaction and insincere pleasantries of the corporate environment create an almost palpable sexual energy throughout the workplace. As counterintuitive as it seems, the cookie cutter monotony of the office is a breeding ground for fantasy. But, like your resume, these feelings are woefully exaggerated.

The people you work with, while reasonably put together at work, are entirely different people when it’s time to clock out. Don’t let a shared disdain for your boss fool you into thinking you have a special connection with someone. These people are just as different off the clock as you are.

Look, we can talk about the good, bad, and litigious of sleeping with a co-worker until we’re blue in the balls, but ultimately, it’s your decision and you should trust your instincts. There are a lot of happy marriages, strong relationships, and otherwise harmless flings that began as yearning stares across the boardroom table. That same stare is also responsible for a lot of keyed cars, divorce settlements, and pink slips. All we can do is provide experiential guidance and hope you boink responsibly.