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Dating Your Boss? Hear What Experts & Those Who Did Say

Should you date you boss? Let’s hear what experts and those who did say about this matter. The pros & cons of dating your boss are also discussed.

Robin | Updated:

Dating Your Boss

You must have often read stories about dating your boss. You have even wondered if it was a bad idea. Now you don’t have to wonder anymore because we have compiled all the information related to whether you can date your boss and all the problems with dating your boss. All this information is collected from experts and people who have dated their boss.

Through this article, you will only be getting authentic information that will make it easier for you to decide whether it is worth dating your boss or not. Not only that, you will be getting valuable tips that will help you in case you choose to date your boss and will save you from all the office drama. Continue reading this article to learn more about dating your boss and its pros and cons.


Should You Date Your Boss? What Experts Say 

According to psychologists, there are high chances for colleagues to fall for each other as they are in close proximity, and working together will let them open with each other and increase the chance of them getting together. Not only that, it is also observed that people who share similar interests are more likely to start dating. 

Now when it comes to dating your boss, experts' opinion is you should be very clear from the start about the pros and cons of the relationship. If this relationship comes with many risk factors, then it is very much likely that the relationship will not work out. For example, your professionalism might be questioned, and you might have a conflict of interest and might have to choose between team and individual interests.

According to experts, it is better to be clear about what your intentions and interests are from the start. If you are thinking of dating your boss just for the sake of personal gains it will not work out in the long run. Your motives should be clear from the start because people will judge you based on these motives.  After considering all these points if you still think dating your boss is the right thing then you can move forward with this idea.

Should You Date Your Boss? What Those Who Did Say 

The best way to decide whether you should do something or not is to learn more from the experience of other people and after that, you can easily decide whether doing the same thing is good for you or not. On Reddit, there are some of the experiences of the women who dated their boss. After reading, you can decide whether you should date your boss or not.

1. He was manipulative

He was older than me by 10 years and would use work to manipulate me. He used his power as my boss to make me believe that I depend on him and that without him and this job, I couldn’t survive. After dating for a few months, I realized I could not let him control my life so I resigned and luckily found a good job.

2. We no longer work together

We used to work in the same company but not in the same department. We met at a company party. He was one of the most caring and extroverted people I have ever met. We fall hard for each other though we would not be seen kissing around the company, we would meet at the elevator and would go for coffee breaks together. Later I got a better job position and had to move away but it was lovely as long it lasted.

3. Criticized at work 

He was my boss at work, and I was just an intern. I was new to work, and he would often guide me soon as we started to date. Once our colleagues found out the reaction was very bad. Since I was in a lower position everyone judged my motives for dating him. They suspected that I was trying to take advantage of his higher post and since I was not hired as a permanent employee it influenced their judgment even more. No matter how capable I was, all my hard work was ignored because I was dating my boss. In the end, I cannot take their criticism anymore and handed in my resignation.

4. We are still together

We meet at a company get-together and start hanging out outside work hours from there onwards we fall in love. We just enjoyed staying in each other's company, but the best thing was that we never let it affect our work now even after 10 years we are still together. Married with a baby along the way.

Weight the Cons of Dating Your Boss 

Dating your boss is not very easy in reality. No matter how good it seems in stories the reality is different. In real life, you need to deal with many problems. Here are some of the cons of dating your boss


Gossip is one of the biggest cons that come with dating your boss. At work, you would be a hot topic once your colleagues find out that you are dating your boss. It is best to keep your relationship private no matter how tempting it is to talk about your relationship to your work friends. Trust us it will not do you any good if your colleagues find out about your relationship with your boss.


Jealousy is another factor that you should keep in mind before you start dating your boss. Once you are in a relationship with someone higher up in the power hierarchy at work it is very much likely for people around you to become jealous. They will find you to be more critical of your work. And you would often find yourself as the target. People would very likely blame you and you are less likely to get credit for your work. They would only assume that you are getting the promotion or any bonus only because of your connections.

Power Imbalance

The power imbalance is another critical factor that you must consider while dating your boss. At times your boss must prioritize work over you. You will always be in a dilemma about whether you should think like an employee or as a partner. It would be very difficult to balance both your work life and your relationship at the same time.

After all these cons we can conclude that dating your boss is not easy and you would need to sacrifice a lot and even must face a lot of problems. In our opinion, it is so much better if you date a sugar daddy. A sugar daddy will not only take care of all your needs but will pamper you endlessly. You can find the best and richest sugar daddies at SugarDaddySeek. On this website, you have endless options that are available for you to choose from. The best thing about SugarDaddySeek is that all the members on the website are verified and hence will save you from a lot of trouble.

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Keep 5 Tips in Mind When Dating Your Boss 

Now even though we know that dating your boss is not easy and you have to go through a lot of trouble, here are some of the tips that will save you from getting in trouble.

1. Know your company policy

One of the most important things that you must know before you start dating your boss is the company policy. Whether your company allows you to date your colleagues or not. And be clear about all the related policies like at Google you can only ask your colleagues out once if they say no, you should back off and not force them to go out with you.

2. Speak for yourself

You should be very confident about what you want in a relationship even if you are dating your boss you must speak for yourself and not let the higher position affect you.

3. Set your boundaries

From the very start, you should set your boundaries. You should mention clearly what you want in a relationship and what you don’t want. You should not always hang around each other at work. You should be clear with what image you are trying to portray at work.

4. Keep it private 

In the beginning, it is best if you can keep the relationship private and be sure to only disclose the information once you are comfortable with each other and comfortable with the fact that people will find out.

5. Consider all the pros and cons 

When it comes to dating your boss, it is best to consider all the pros and cons. You should consider all the risks and then decide whether it is worth it to risk everything for a relationship that you might already know will not last long.


Dating your boss is not easy as we already know. It has many cons and is not worth the tension and stresses it brings with it. It would be better to get a date with a sugar daddy not only it will save you from all the trouble. You would be happy financially and mentally relaxed and would even have endless pampering too.

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About the Author

Robin is a Content Marketer at SugarDaddySeek based in New York. When he’s not busy writing you can catch him playing tennis or binge-watching Netflix series.

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