Good morning, Secret Agent Man. Your mission, should you choose to accept it, involves a hook up with forbidden prey. It is essential that you act alone on your quest, wingmen are strictly prohibited. She is a civilian, though considered highly dangerous to your professional and/or social status. You have forty-eight hours to attract your potential partner and many months to cover up your mission…

Ok, so not every guy gets to fulfill his childhood dreams of becoming a secret agent, carrying out elaborate heists to save the world. Although maturity – or reality – may have taught you that you’ll never have the rush of chasing bad guys with guns blazing, there is still excitement to be had if only on a smaller scale. At some point, almost everyone finds themselves in a situation when the prize they seek is seemingly unattainable, making it even more tempting. Setting your sights on a coworker or your best friend’s little sister can be a difficult maneuver to pull off, but if Tom Cruise can lead the “Impossible Mission Force,” there’s no reason you can’t pull the “Impossible Hook Up.”

Sweep for Landmines

Before making any drastic moves, access the possible damage your pursuit could cause. It doesn’t sound very romantic, but taking a few minutes to read through the employee handbook’s “Dating/Fraternizing” section could save you a lot of time wondering if what you’re doing is permitted and in the long run could save your job, if your tryst is discovered. There’s a good chance that if you’ve got a crush on your manager or subordinate, your company will consider the relationship unacceptable and should stay filed as a fantasy. On the other hand, if you’ve got a thing for the redhead from IT who crawls under your desk every time your computer malfunctions, you can begin to plot your course.

If your love interest is someone in your social circle, the lines of right and wrong aren’t as easy to determine. What you may consider friendly fire might be considered fraternizing with the enemy by your friend. Take a pal’s younger sister for instance: Over the years, your friends have probably prodded him about his attractive sibling and his reactions should be a good sign for you. If he laughs off the teasing, he might be ok with you dating his sister, but if he gets defensive or angry, there’s a good chance he’s not down with her dating anyone – especially someone he expects to be loyal comrade. The question you have to ask yourself is, how bad do you want it?

Maintain Radio Silence

Keeping your friends in the dark about your relationship is tougher than coworkers who generally don’t butt into your personal life and can be quieted with vague responses or blatant lies if the subject arises. To avoid being caught off guard, don’t make a habit of bringing the girl to your apartment or frequent hang outs. Having her over to your place may seem conducive to your laziness, but you never know if Joe’s going to stop by to borrow a hammer or invite you to play golf only to find Dave’s ex girlfriend eating cereal in your boxers. Instead, create a bunker for two in foreign territory, such as a swanky martini bar with no happy hour specials where friends are unlikely to venture.

Turning off your phone when you’re with the girl is an easy way to steer clear of your friend’s probing question. It’s better to use a flaky excuse like poor cell phone reception to explain your absence than to dodge interrogations or try covering up her voice in the background when you’re sitting shotgun in her Prius.

Loose Lips Sink Ships

Guys don’t really “gush” about a new girl they’re sleeping with, but it can be hard to keep quiet when you’re the first man to conquer a foreign land, or bed your pal’s barely legal yet ridiculously hot sister. It’s better to feign interest in graduate school courses while actually tiptoeing to the sorority house’s backdoor twice a week than to trust a confidant. The juicier the dirt, the more likely your secret will fall into the wrong (read: very angry) hands and those hands might just take it out on your face.

The same thing goes for a relationship at work. Don’t spill your news over the cubicle wall; you never know who else may be listening or what alliances this colleague has around the office. In the competitive job market, your relationship could become a liability. Even if you’re not breaking any rules, Human Resources may require that you disclose any romantic or sexual relationship to them and may penalize you and your girl if they have to hear about your liaisons from a third party.

Starburst Maneuver

To avoid close surveillance, keep up your normal routine. If you’re the type of guy who is constantly going out with his buddies, meeting girls and getting phone numbers, you must continue to do so. Don’t try to overcompensate if you are usually low key; while this may be welcomed behavior in your bachelor circle, your allies will suspect foul play.

Even the sneakiest spies can leave a trail if they’re not careful. You may have thought you were covering your tracks, but if a mutual acquaintance has been asking you too many questions and seems suspicious, you may have to throw them a curveball to keep from getting nabbed. It might really tick off the girl you’re actually seeing, but bringing a different date to your company’s Christmas party or getting a stranger’s number at the bar could distract any wary audiences. If you’re in cahoots, she’ll understand that you have to lose the occasional battle to win the war. Indiana Jones hated snakes but he never would have saved the Lost Ark if he let that obstacle stand in his way.

You’re under specific instructions to complete this task without getting caught. This could be the most dangerous mission you ever accept in your bachelor career. You will face extreme peril and possible torture if you slip up even once. Enemies lurk around every corner with the goal of exposing your relationship in their sights. If you train your eagle eye to watch for foes and booby traps, you can carry out this covert mission and bag the impossible hook up. This column will self-destruct in five seconds…

Originally published on PureStyle Magazine