Hookup With The Boss: 9 Things to Know When Casual Relationships Impact Professional Life

Dating A Boss

Casual relationships around the office aren’t anything new. People often hook up with their coworkers. It’s an entirely human thing. When people spend a lot of time together, they learn about each other and develop an attraction. 

But it’s not just peers that start having sex. People at higher positions often get involved with their employees. And when it comes to sexual attraction, there are no work boundaries. There are company boundaries, but they can be avoided. 

It’s possible to hookup with your boss, but there are some things you need to be prepared for. This is not something you should get into lightly. Hooking up with your boss will profoundly impact your professional life, even if you are keeping things casual. 

1. You Need to be Extra Careful 

When you get into a sexual relationship with someone, you don’t know each other at first. That person might seem like just your manager or boss. However, as time passes and you see each other more often, you will start to see them differently. 

Simply put, you will stop perceiving him or her as your superior. Instead, you will see each other as just two people who have sex or even as a couple. This is a sign that you are slowly starting to lose your boundaries. 

You won’t see each other as two people that work somewhere together. If this happens, you can easily get into some difficult situations. You might get exposed, start behaving unprofessionally, manipulate each other, and much more. 

People need to be careful with any kind of office relationship, but when you are having sex with your boss, you need to be extra cautious. After all, he or she has the power to ruin your place at the workplace and set your career back. 

On the other hand, you can also accidentally ruin your superior’s reputation and career. In most companies, it’s simply forbidden for employees and their superiors to be romantically involved. This is why you need to be extremely cautious when stepping into something like this. 

2. Don’t Antagonize Him/Her! 

Your relationship is one thing, and your work is another. However, when you become involved, these boundaries often fade. Face it, no matter what is happening in your relationship, or how dominant you are, your boss will always have power over you in the workplace. 

He or she can hurt you very much if they want to. They might even do it without you knowing it. Lower-level employees simply don’t have access to all information and processes that happen within the company. 

If you are fighting or having issues in your relationship, the feud could easily leak into your professional life. People are often bitter and vengeful in relationships or when they end. Your superior might decide to use their power against you. 

What’s even worse is that they could do it without you knowing. That’s why you shouldn’t get too personal in your relationship. It will affect things both when they are good and when they are bad. Keep things cool, and always try to make reasonable decisions. 

Flirt With Boss

3. If You Decide to Start Something, Take it Slowly 

Naturally, whenever you get into a relationship, you should move slowly. It’s the smart thing to do. If not, you will get invested too quickly and regret it later. This is the easiest way to get bombarded with emotions and form unrealistic expectations. 

You need to be slow about it and get to know that person. Do this even before you have anything with him or her. You need to be sure that you can trust that person and that you won’t get abused or manipulated in your casual relationship. 

Successful people are used to getting what they want. A lot of them look at people “beneath them” as less important. In a lot of situations, they just want to use their employees sexually and think that they deserve this privilege. 

Don’t do anything quickly. Make them wait and see if they are willing to make an effort around you. If they quickly lose interest, you are probably better off without them. This just means that they looked at you as just another employee for them to “bang.” 

I’m not saying that you should be looking for something serious. On the contrary, you shouldn’t ever consider this option. However, even for casual dating, there needs to be a certain level of trust and respect between two people. 

4. Work is Work; Sex is Sex! 

Never, NEVER let these mix up together. Of course, you will do it as soon as you hook up with your boss, but there shouldn’t be anything more. All of your work routines should remain the same, phone use, communication, and career goals. 

You absolutely can’t afford anyone being suspicious of you two having anything together. Both of you can get fired and set your careers back in so many ways. People lose their credibility and reputation when they get exposed. 

There need to be zero changes in your work behavior. That’s something that both of you need to agree on, and if you start breaking the agreement, break off your whole relationship. Don’t talk ever about your relationship while at work, or any aspect of your romance. 

At the same time, don’t talk about work while you are together. Lots of people are tempted to ask for favors or opportunities from their superiors. But this is an extremely slippery slope that could lead to dozens of different problems. 

5. Never Ever Expect Anything Serious 

Yes, there are a lot of relationships that started in the workplace. However, this doesn’t mean that you should think about this at the very start. When you break up with someone you care for, you don’t want to see them for some time. It’s a normal reaction, and everyone does this to get over their ex. 

However, if you are involved with someone from work, you don’t have a choice. You will see that person every day. In this situation, it’s even worse. That person is your superior, and he or she will boss you around daily. 

It’s something that only a small number of people can handle. This can significantly affect your work performance and not to mention your personal feelings and emotions. In these kinds of situations, the only thing you can do is quit your job. 

On the other hand, if you are the one who broke his/her heart, they might want to pay you back through their position. It’s fundamental human nature, and this is why your goal shouldn’t be expecting anything serious. The only way for this to happen is if you both “passively” fall for each other and build incredible trust between you. 

You simply know when you are in that place with someone. From that point, you can think about the options you have. However, this doesn’t mean that it will be easy. At the least, one of you will have to find a job somewhere else to date each other publicly. 

6. Be Sure That The Attraction is Mutual 

You can’t allow yourself to make a mistake in these situations. You need to be 100% that your boss is into you as well. Sometimes people do flirt, but that’s as far as they plan to go. In fact, there are a handful of people who would sleep with their boss or employees.

It’s simply a complicated arrangement that makes your life more difficult. I’m not saying you shouldn’t do this, but you need to be sure you’ve read the signs accurately. If not, you might end up getting fired or jeopardizing your work. 

Hitting on your boss without them being interested in you is one of the worst things you can do at work. There is no good scenario in this case. Even if your boss is mild, he or she will see you differently forever. Simply put, they won’t trust you or give you the opportunities you might deserve. 

In the worst-case scenario, you will be fired instantly. Conduct a thorough investigation and “feel out” the situation as best as you can. In fact, he or she should ideally hit on you. After all, they are the ones who have power over you in your relationship. 

7. Never Ever Talk About It With Anyone! 

If you started having sex with your boss, make sure to never talk about this with anyone. The stakes are simply too high. It can be challenging to keep such a big part of your life a secret, but you must be prepared to do this at all times. 

If your friends are annoying you with questions about your love life, why you aren’t seeing anyone or trying to hook you up with other people, you will need to be prepared to lie to them. People gossip all the time and tell secrets. 

Knowing that someone is sleeping with their boss is as juicy as it gets. If your boss finds out you’ve told this to someone, he or she might freak out, look to cover themselves by scarifying you, some coworker might try and blackmail you, and so on.

There are so many things that can go wrong. If you can’t keep a secret and be completely anonymous, you shouldn’t get into a sexual relationship with your boss. 

8. It’s Not Always Easy to Separate Your Feelings 

Everything will be more complicated once you step into this kind of relationship. If you see your boss going to a big party that’s only for the higher-ups, you might feel bad about yourself. If he or she doesn’t share information that could help you keep your job or progress, you might feel betrayed. 

If your superior yells at you at work for making a big mistake, it won’t be “just your boss” yelling at you. You might have mixed feelings and feel even worse than in normal circumstances. You need to turn off your emotions entirely and keep your eyes and ears closed. 

This is not something everyone can do. It usually starts this way, but most people begin to develop stronger feelings after some time, and this is when things go downhill. You will have to swallow your pride and ignore what you’re feeling to keep this kind of relationship going. 

9. You Can’t Expect to be Exclusive! 

Casual relationships are just that, casual. This is something both of you need to be aware of. You need to be prepared for this. As we mentioned earlier, influential people are often dominant both in their professional and personal lives. 

If your hookup is involved with other people as well, you shouldn’t be surprised. You shouldn’t expect it, and it goes both ways. Remember, what you are doing is just indulging your sexual desire, nothing more. There shouldn’t be any rules or limits set between you two. 

Things are complicated enough, and if you have expectations from each other, you will only make it even worse. At the same time, when you work together, it’s even more difficult to hide if you’re lying or having someone else. 

If things progress naturally to something more serious between you, then be it, but if not, you need to lower your expectations. 

Bottom Line 

Having sex with your boss can be a fantastic experience. These kinds of relationships bring a lot of excitement, mystery, and experimentation. However, you need to ask yourself, is it worth it? If you aren’t ready to deal with all of the things we mentioned, then probably not. 

A lot of people have hooked up with someone from the office. There are even a lot of long-lasting relationships that started this way. But for this to happen, you need to have a good approach and move slowly.