10 reasons not to date your boss

1. The most obvious reason not to date your boss is that if the two of you ever break up, your boss might fire you. Sure, that's illegal. And yes, you could probably take your boss to court and you would most likely win something. But do you really want to go through all that? Avoid the headaches.
2. Nepotism is a concern. Your boss might start showing you special treatment, or you might start showing your boss special treatment on the job. While this might not seem like a problem for you, it really is. The other employees will most definitely notice, even if you and the boss think you're being discrete. If nothing else, this builds bad relationships between you and your fellow employees, and that can make your job all that much harder.
3. But even if nepotism doesn't truly exist, your co-workers are likely to bear some grudges, at least some of them. Even if special treatment isn't involved, some employees are going to believe it's going on anyway. You don't need that kind of trouble.
4. What about your next raise? If you are dating your boss, it will be impossible for him or her to properly decide upon what level of raise you should get. Even if you have done a fantastic job, the boss might not want to give you too much of a raise because he or she could fear it will look like nepotism.
5. Or just as bad, the boss you are dating could give you a great big raise, one you might not deserve. The money sounds great, but other employees will find out. Believe me, other employees will find out. Even if your boss and human resources department promise and swear that employees can't find out what one another makes financially, don't believe it. People talk. Word gets out. This could be more trouble brewing for you on the job.
6. What if you and the boss break up and you go on a hunt for a new job? Would you feel comfortable asking him or her to be a reference? Most likely not. Think the two of you will never break up? Maybe not, but don't bet on that. It might happen or it might not, but it's best to play it safe.
7. What if you and the boss break up but you remain on the job? Do you think it will be a pleasant work environment? Do you think your boss and former girlfriend or boyfriend will be able to treat you fairly? Think about it.
8. He or she might be your significant other, but they still are your boss. That means there will be times they will have to put the company before you. In fact, there might be a lot of times they have to do this, and they might be more willing to do it since you work for the same company. Are you ready to handle being second at times?
9. Most places will have a policy concerning inter-office relationships. If you are going to enter a relationship with your boss, or even another co-worker, make sure you know those rules. Nowadays most companies won't outright disallow such behavior, but they'll still likely have some sort of policy. You don't want to break that policy. It could get you in trouble at work, even if your boyfriend or girlfriend is your boss.
10. What if you and your boss/lover have a workplace disagreement? Will it then boil over into a personal argument? Can you set up strict boundaries between work and your personal life?

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