You probably shouldn’t.
It makes things a lot less complicated for you if you don’t.
However, if you like him that much and are intent on dating, you should strongly consider either changing departments or having him do it.
You should even consider changing jobs.
Your boss is someone with responsibility.
He is the head and he gives direction to the subordinates.
The first thing you would need to worry about if you were to date your boss is how it would affect the office dynamic.
There are other employees that may observe the both of you.
They may begin to get the sense that there is some favoritism going on.
This may actually not be the case but it is easy for other employees to draw this conclusion.
This is especially true if the employees are unhappy about something.
They may be unhappy about pay and blame you for getting more pay just because you are dating the boss.
This may not be true at all. You may be getting more pay because you work harder, longer and are more experienced.
However, these employees don’t look at it in that way because you are an easy target.
Being able to blame you and the relationship you have with the boss is a lot easier to do than look at themselves and what they may be doing wrong in their positions.
You essentially become a scapegoat.
This could be with salary, work condition, hours, etc.
Whatever an employee may disapprove of, they could easily cast the blame on you and your relationship with the boss.
Hence, it can get really tricky when you date a boss of your department.
The office dynamics can totally change.
Are you willing to deal with this?
Do you even think you truly can?
This is something that you really have to think about before you decide to make a move.
It can be so easy to get so rooted in what you want and desire that you don’t consider the ramifications of what could happen.
Again, as I mentioned earlier, if you want so badly to date this boss, you can either request a transfer to a different department or have him do it.
It will be a lot easier for the both of you to date when he isn’t directly responsible in managing your other work colleagues.
You should also consider the fact that there may be the temptation to bring work home or into your relationship.
He may be very busy and stressed with all of his responsibilities.
You may be having dinner with him and all he wants to talk about is work.
This can be very difficult to bear.
You may start feeling as though he is married to his work and your presence is not really being acknowledged.
Again, he is a boss and has more responsibilities than you do.
If you were to date him, you would need to ensure that he can separate his work life from his private life.
If he is unwilling to do this, you will have a hard time moving the relationship forward.