The Do’s and Don’ts of the Office Fling

Fooling around with a coworker is like screwing your neighbor; so very convenient (it’s the drive-through of hookups), yet still fraught with danger (potentially awkward run-ins, forced togetherness). Luckily, the benefits of this excellently illicit activity far outweigh the pitfalls, especially inasmuch as it provides a welcome release for the stiletto-clad-and-tight skirted sexual tension of over-caffeinated late-night brainstorming sessions. Just follow these rules of play and you’ll come out the satisfied winner in your high-stakes game of office nookie.

Tread Lightly

1) Do: Seize the Moment

Intra-office propositioning takes some forethought, but once you’ve found an equally interested party, your course of action should be swift and direct lest the moment be lost entirely. It’s vital, however, that your first move not be made while cornering your target under the fluorescent glow of the break room, so if it isn’t the office-party time of year, then any liquor-soaked office outing should provide you with the impetus necessary to broach the subject in without sending your potential partner screaming to the H.R. office. If you prefer a less direct method of communication, then a well-timed text message can help you arrange a post-meeting rendezvous in the stairwell. Just remember that emailing on the company server is strictly off-limits… you don’t want to leave a paper trail, especially if your preferred pickup technique involves lewd videos and nsfw imagery.

Don’t: Brag to Your Coworkers… Yet

From jealous competitors to petty underlings, your office is chock full of people ready to take you down at the slightest hint of vulnerability or rule-bending. Don’t assume that any of your officemates are completely trustworthy; as a rule, and especially if your office has a no-fraternization policy, it’s better to keep your tawdry extracurriculars to yourself, at least until you can replace the water cooler play-by-play with a post-post-post-game wrap-up that highlights your long-completed climb up your coworker’s corporate ladder while minimizing the chances anyone’s going to be able to use your conquests against you.   

Be Discreet

2) Do: Have Copy Room Sex            

After hours. Because you can. And because it’s one of those things that that you need to check off your list. A tip, though: figure out if your office is under video surveillance, and if it is, wikiresearch how to dismantle said surveillance system so your indiscretions don’t follow you to the Board room ten years down the road. 

Don’t: O.D. on the O.D.A.

O.D.A.’s – Office Displays of Affection – will ruin your office rep faster than admitting you’ve been running a money laundering racket out of your cubicle during your annual review. People will quickly catch on to your stolen glances and secret code words, so keep the winks to a minimum and avoid at all costs holding hands, giving back rubs or otherwise broadcasting your after-hours intentions to the world. In fact, it’s probably better to avoid your partner in crime as much as possible while in the office, and never, ever show up together in the morning holding hands and sharing a bagel.

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Ready for Impact:

3) Do: Prepare for Things to Get Ugly.

Statistics say that 34% of office romances end in marriage. This seems neither here nor there, but if you find yourself in one of the 66% of office relationships that don’t make it all the way to the altar, then you’re going to have to figure out a way to bow out semi-gracefully without making the rest of your office life the center of a crapstorm of awkward. If you’re her boss, then there’s a good chance that a mishandled breakup will come back to haunt you faster than you’d expect. If she’s your boss, then #1, well played, but #2, ready yourself for the onslaught of knowing looks and smug chuckles if and when you either get a promotion or get canned.

Establishing at the outset that your fling has a limited shelf life is one way to avoid the nasty inevitability of a woman scorned (or, however unexpectedly, your own heartbreak). The woman in this equation probably doesn’t want to face the possibility of nuclear hookup-related fallout either, so laying down ground rules before things get too heavy is the key to successfully navigating the final days of any office fling. In the end, though, just acknowledging the fact that you’re both in for some weirdness will help you mentally prepare yourself (and remind you to schedule some back-to-back business trips should the going get unbearable).

Don’t: Be the One to Make Things Weird.

All good things must come to an end, but that in no way guarantees that most things come to a good end. Though you might expect to be the one calling the shots, if she calls things off before you can, you must resist the urge to talk smack and spread rumors about what a whorey skank she is. Not only will this method of attack completely backfire – you’ll end up looking like an obsessed psycho who can’t keep his sh** together – but it will give the rest of the office reason to take sides, which usually doesn’t work out so well for the aggressor (you). Attempt to not completely freak out by channeling your energy into kicking ass on your next project, or take your mind off of unpleasant things by seeking comfort in the arms of someone from another department. Either way, you’ll always have your broken desk lamp and artful Xeroxes to remind you of how fun it was while it lasted.

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