Knowing the Risks Beforehand
Familiarize yourself with your company’s fraternization policies. Many companies have a zero-tolerance policy for interoffice romance. Make a point to familiarize yourself with written policies on fraternization. Your Human Resources department has these policies on file.
Weigh the pros and cons. Consider your future goals and be clear to yourself about what your job means to you. If you are uncomfortable with the possibility that this rendezvous could end up negatively affecting your career, then it probably is not a good idea to pursue a one night stand with a coworker. Pros may include: having a one night stand with a person you're familiar with because you work together, having at least one thing in common (work) with the partner for the one night stand, and the exciting, “forbidden” nature of the affair. Some cons could be: one of you could end up being fired, things could become awkward at work between the two of you, work place gossip may spread, and your reputation might be tarnished.
Don’t confuse workplace solidarity with desire or love. Do not pursue the affair in order to escape your day-to-day work struggles. Today, many people are unsatisfied with their jobs, but this does not mean you should sleep with your co-worker who happens to sympathize with you; do not confuse sympathy with love or desire. Sympathy is an understanding or common feeling between people, generally in a negative context. For example, you can sympathize with someone who you do not even know because you share a common negative experience. Love is an intense feeling of affection or desire, where you want to get to know a person on a more intimate level.
Have an exit strategy. If you do decide to pursue the affair, know your game plan. Consider the worst case scenario, and have an exit strategy if things go south. Think about whether you would be willing to quit your job, and have a possible back-up in case things end up badly. Before the one-night stand, you can prepare your exit strategy by doing the following: Make sure your resume, website, or work portfolio is up to date. Contact colleagues and people you know from previous jobs for references and recommendations. Look into the company’s other departments or job banks online to see if there are job openings you can apply to, or register with a temp agency.
Getting to Know Your Coworker
Ensure your coworker is interested. Don’t just ask any coworker. Ensure they are interested by reading their body language. If they are giving you signals that they may be interested in you, then proceed. These signals can be direct, like maintaining eye contact, smiling, or touching you while they speak. Or, they can be indirect, like touching their hair, neck, or face while talking to you. If they adopt closed body language, for example, turning away from you, avoiding eye contact, or any contact at all, then chances are they are not interested. If you are truly unsure if your coworker is interested, do not fret. You can try more direct contact like asking for their phone number to see how they react. Or, you could try telling them a joke to see if they laugh, and perhaps a conversation could start from there.
Be discreet. Make your advances confidential. This will gain your coworker’s trust and increase your rate of success. Do not make any big moves at the office, like being overly flirty, or suggesting you do something during work hours or at the office. This will likely scare them away.
Move slowly. Before you attempt to ask them, get to know them first. Try to find things you have in common with your coworker besides work. Ask them about their hobbies or what they like to do on the weekend. Ask them what their favorite foods are, or ask them about the different places they have traveled to or would like to travel to.
Meeting with Your Coworker
Bring up the topic. Once you have gauged the interest of your coworker and you have developed a basic level of camaraderie, you can attempt to bring up the topic of the one-night stand. Your opening line could go something like this: “Hey, I really like talking with you. Would you like to take this conversation back to my place?” You can be more straightforward and ask, “Would you be interested in sleeping/having sex with me?”
Be honest with your coworker. Be clear about what you want out of the affair. If it is simply a one-night stand that you are interested in, or if you are willing to consider the possibility of something more, be upfront about it. Let the person know your feelings and how you see the relationship developing in the future. An example of how you can approach this is by saying, “Before we go through with this, I would like to be clear about my feelings and expectations.” This is also the time where you should discuss with your coworker privacy issues such disclosing details with other coworkers and posting things on Facebook about the affair.
Arrange a time and place to meet. Once you have gotten to know your coworker and you are sure they are interested, arrange to meet them somewhere after work or on the weekend. To ensure privacy and your chances of success, meet at a bar or restaurant that you know your other coworkers do not frequent.
Dealing with the Aftermath
Stay professional. Maintain your regular office routines and be cautious about how you behave around other coworkers. While at work, do not go out of your way to be overly attentive or nice to your “special” coworker. Do not openly flirt with your coworker as this can cause suspicion among other coworkers. Do not email or instant message your coworker at work about the encounter or personal matters. Limit your conversations to strictly business matters.
Do not kiss and tell. Agree to keep things secret by not telling other coworkers about the affair. If you have to tell someone about the affair, make sure it is a friend who has no connection to your work place. One of the biggest mistakes you can make here is by posting about the affair on Facebook. Remember, once something is on Facebook, it is hard to take it back.
Manage the situation. If caught while trying to keep things secret, be prepared to deal with backlash. Have a risk management strategy by thinking ahead about how to mitigate, minimize, and/or manage the situation. Log more hours at the office. Take on new responsibilities and projects. Be proactive about promoting your accomplishments.
Be upfront yet professional if your boss finds out. If your boss confronts you about the situation, do not lie about it. Own up to it and offer valid solutions. If it was a one-time thing, let your boss know it is over. If it has developed into something more serious, don’t offer to end the affair but do let your boss know that you are sorry that they did not hear it from you first.
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