Darlin, unfortunately most, if not all workplaces happen to have rules against boss/ subordinate relationships. If i were in your position, check to see what rules your workplace has. If there are none, I would tread carefully. Not only could there be a problem if it doesn't work out in just having relations with someone that works with you, but having a relationship with your boss and it does not go the way you would like, it could not be good if he is one of those types that gets pissy towards a date that did not go well or a failed relationship. Also check this out lovepanky. com/my-life/work-and-office/tips-to-keep-in-mind-when-you-date-your-boss. There are some great tips there.