How to Date Your Boss

It’s not the ideal situation, and most people will warn you against it, but sometimes you can be attracted to the exact person you shouldn’t be: your boss. This doesn’t have to be a dramatic, fated relationship. In fact, it can be healthy and functional, as long as you realize beforehand that special parameters have to be considered, and know the steps to take.

Difficulty: Moderate

Instructions

1. Confirm your attraction by going on an informal first date, or grabbing lunch during the day. Working together provides a certain kind of chemistry; so before you both decide that you want to pursue a romantic relationship, ensure that you have the same inclination outside of the workplace.

2. Examine your company’s policy on dating within the workplace. Most human resource departments will have a clause on this very subject, especially when it comes to superiors and subordinates. If your company prohibits this behavior, discuss this with your potential partner.

3. Conduct your relationship outside of office hours, rather than on the job.

4. Be professional at all times, and try to treat your partner the same as you treat the rest of your co-workers.

5. Take time for yourself. Spending all your time with your partner, both at work and outside of work, can leave little room for necessary alone time.

6. Keep your business issues with your boss separate from your personal issues with your partner, while in the office and at home.

Tips & Warnings

• Be prepared for potential negative consequences, which can include termination.
• Don’t engage in physical activity on the job. It may seem fun for the moment, but the fallout can be severe if you are get caught in the act.
• Be careful if or when you get a promotion, as it can appear to be preferential treatment if your partner is also your direct supervisor.