Affair Dating / Dating Tips & Advice

Initiating an Affair With a Coworker Without Triggering an HR Red Light

An office affair gone wrong can hurt your marriage and your career. It’s a risky thing, there is no doubt about that, but this is what makes it even more exciting. Most people like this kind of thrill. This makes the sex even better. 

However, if you plan on starting an affair at work, you need to do everything in your power not to get caught. As we mentioned earlier, you don’t want to ruin your life over an affair, right? Your greatest worry should be HR as they are the ones making sure employees “behave” themselves. 

But before we get into that, let’s see whether you are reading the signs right and if you are about to start an affair. 

Signs You Might Be Getting Into an Affair

You Are Flirting Often 

People love to flirt, and some will flirt even if they are not interested in anything more. However, if you are always flirting with one person and you can’t wait to meet in the hallway, something is going on. 

If you are both showing interest in each other, then there is no doubt about it. If you are both initiating conversations and flirting is not one-sided, chances are you’re into each other. Still, if you like someone and would like to initiate conversations, just show interest, and see how he or she reacts. 

But if you are the only one involved in the whole thing, don’t push it. You don’t want that person to spread the word about you. If you go too far, they might even report you to HR for sexual harassment. 

You’ve Made Your Own Inside Jokes 

When two people have their own inside jokes, this is a sign that they are really close. Still, it doesn’t mean that you are close romantically. If there is a bit of flirting added and your share secrets that neither of you tells other people, you might be interested in each other. 

This sets your relationship apart from everyone else, makes it intriguing, and unique. For example, if you have to communicate constantly about some work orders and you use every opportunity to share some information while flirting a bit, you’re definitely into each other. 

You Made a Connection 

People can connect at work in many different ways. Some people talk about work. Others talk about everything but, and some talk about how their marriages are unfulfilling. No matter how you connect with someone, this will open up options.

If you generally enjoy each other’s company and love talking, there might be something there. It’s only a matter of time before one of you makes a move, and you turn your connection into something more serious. 

These are some of the ways office affairs usually start. Of course, there are many other ways you can hook up with someone. Now, let’s see how you can start and maintain an affair at work without getting caught by HR.

Talk Openly About Your Situation

There are a lot of open people, and they like to talk about things. If you feel that you can do this with someone who you like, go for it. This will make things so much easier, and you will instantly know where you’re at. 

When you are having a conversation, and there is nobody around, simply start talking about the chemistry you two have and where you would like it to go. Of course, do this privately in a real conversation and don’t send messages or chat online. 

Don’t give the other person ammo to report you to HR. On the other hand, if your coworker is also interested, you can discuss how you can organize your affair and set up rules that will protect you both from getting caught.

Promise Each Other That This is Only About Sex 

Most of those office affair disasters you heard about have one thing in common – emotions. When one person or both people in an affair catch feelings, things start to complicate. This is not the right way to start a relationship and get a divorce, and it almost never works out. 

Some couples are like “we’ll see where the relationship takes us,” and this is a big mistake. If you are unhappy with your marriage and you are considering getting divorced, do that first before you start looking for another relationship. The main reason why you should do this is jealousy. 

If you fall for the other person, you will be jealous of their spouse, and this could create fights and workplace outbursts. All of this will lead to being exposed, and this will then cause more problems in your life. Limit yourselves to sex only, and if you realize that you are starting to fall for the other person, break it off. 

You should expect the other person to do the same. Remember, this is only an adventure that should be as least complicated as possible. It should help you catch a break from married life and not make it even worse. 

Don’t be Obvious 

Even when you’re just flirting at work, you shouldn’t do it while there are people around. Why? People talk, and word gets around very quickly, especially in a work environment. People are bored with their everyday routines, and they can’t wait for something new to happen. 

In those kinds of situations, a small false rumor can turn into something huge. When this kind of talk reaches the HR department, you can get into huge trouble. This happened to many people who didn’t even have sex. Their coworkers simply misunderstood them. 

If you are going to start an office affair, you must keep it on the down-low. Don’t flirt in front of others, don’t show your affection at work, and definitely avoid hooking up while at work. 

Don’t Kiss and Tell 

This goes hand in hand with the previous point we made, but it still needs to be said. DO NOT talk about your affair with anyone. No matter if you just started the relationship, you’ve been in it for a while, or you are planning to make a move, you shouldn’t mention it to anyone. 

Sure, you can talk about it with your best friend that doesn’t have anything to do with your work, your coworkers, or the place where you work. However, anyone that is connected to your work in some way shouldn’t know anything about your affair. 

Again, rumors travel around really fast, and a lot of people like to gossip. You don’t want to become a victim of this nasty habit. 

Date Outside

Meet Outside of Work Only 

Most office affairs start at work, and they stay there. This is the worst thing you can do. You need to establish this rule at the very beginning – no sex at work. Sure, it can be exciting knowing that nobody should see you doing it on Bob’s desk, but it’s also very risky. 

You can get away with it several times, but after a while, you will get sloppy and forget if there is a meeting, if someone is coming around the office, or if someone is working overtime. You only have to get caught once for the whole thing to blow over your head. 

Make it a rule to always hook up outside of work without any chance of getting caught. Furthermore, you shouldn’t meet up on the street in front of your office. Leave at separate times and find a rendezvous where you can meet up and go someplace where you can be alone. 

Talk About Hooking up Outside of Work 

One of the best ways to initiate an affair with a coworker is to do it outside of work. This will put him or her in a better place, and they won’t think about consequences right away. Simply put, they will be in a better mood. 

If you bump into each other outside of work and you start talking as you usually do, this might be the best opportunity to hook up. At the same time, if he or she is not interested, they won’t have any evidence to prove you wanted to be more than just coworkers. 

Furthermore, the HR department doesn’t have any authority over what happens outside of work. You won’t be liable in any way. At that point, it will only be he said she said, and even if that person reports you to HR, they won’t do anything. They’ll just quiet down the situation. 

Meet up in Neutral Parts of Town 

If you are already in an affair at work, you need to be a bit strategic to avoid getting caught by human resources. We just mentioned that HR doesn’t hold any power over you outside of work. However, if they find out about your activities outside of your office, they can use that information against you while you are at work. 

For example, if someone sees you two walking around town freely holding hands, they might tell HR. In these situations, HR will keep a close eye on you two and put you in inconvenient situations to see how you will react. Simply put, you will be on the radar and this won’t be a comfortable experience. 

It’s best to stay away from so-called “danger zones” and don’t meet up around your work or your homes. At the same time, avoid going out in public areas where you are likely to come across someone who knows you both. 

Set Apart Your Relationship and Work 

As soon as you start an affair, you need to separate sex and work altogether. Just because you are both enjoying wild sex doesn’t mean you should let it affect your lives. Don’t look at work any differently just because you are sleeping with someone who works with you. 

This is especially important if you work together or one of you answers to another. Don’t let your job and productivity suffer because of your relationship. When you find out that the other person is ruthless about it and it doesn’t affect them in any way, you might feel hurt, and this could lead to other problems. 

The same thing could happen to the other person. If you see that they aren’t handling the whole situation well, try and talk some sense into them. If not, end it on time because having an office affair requires discipline and maturity. 

Act Naturally Around Each Other 

As much as things change when in an affair, they don’t at the same time, if that makes sense. Yes, you should make sure to keep all of your extra activities secret and outside of work. However, this doesn’t mean you should be utterly indifferent to each other while at work. 

No, you should continue your work relationship as usual. If this involves flirting from time to time, so be it. In most cases, it’s more suspicious when two people are avoiding each other and acting like robots when in the same room together. 

Simply put, the best way not to trigger a red light is to be natural and continue acting the way you did earlier. Still, we have to mention again that you need to set boundaries and avoid getting caught in the moment while at work. 


Workplace affairs are off-limits, and this is what makes them so exciting for most people. Still, it’s possible to have one without any issues. It’s all about being able to handle your emotions and having that trust between each other. Have fun, and enjoy your hot fling!

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