The safest avenue to go about telling your boss you like him is to do so after having built a rapport with him outside of the workplace.
Telling your boss you like him at your workplace compels him to turn you down.
A question of professionalism arises.
He isn’t comfortable talking about it at the workplace, as he believes that it is a professional environment, and he is the one that everyone is looking to for leadership.
This threatens his position and the respect of his employees.
Yes, guys date older girls, and this has become that much more common in a society where women have financial agency through the work force.
There is a limit though.
Naturally, most people look for someone around their age or closer to their age, whether it be older or younger, when they are seeking someone to date.
A guy does the same.
He doesn’t mind dating a girl who is older, as long as she is closer to his age.