text: It's a big risk especially if it's your boss. There will be favoritism and if it shows, your coworkers will be really upset. Just keep it under wraps. If they know you're dating the boss and you get promoted, they'll say it's because you're dating him, not because you're qualified.\n\nPlus, if you break up he might pick at you for little things and unfairly fire you. Or, things could get awkward. Just be professional in the workplace and keep your relationship outside. Don't bring your personal problems with each other or fights in.