My boss has been hinting that he is interested in me and has asked me out more than once. I have politely declined up to now because I’m not sure about how it will look and affect my relationship with teammates. To his credit, he has been professional at work. What should I do?
Dear Love Actually,
Relationships with someone at the workplace can be exciting and complicated affairs: exciting, that is, if you welcome it and it is a legitimate one; complicated, because in some work settings, it is discouraged, even forbidden, to be romantically involved with a colleague, much less between a superior and a subordinate. Some employers might see such relationships as possibly compromising personal judgement, fair play or putting company or clients’ interests at risk. Under such circumstances, do not enter into this relationship. If there is strong mutual attraction, then only pursue it when one of you leaves the company.
If strict prohibition does not exist, you are right to be concerned that your colleagues may perceive favouritism. Some may wonder if you are going along with the attention of a superior only because you feel pressured to do so. I take it that in your context, this thankfully might not be so.
If the above circumstances are not applicable, and if you are open to exploring this possibility, how should you approach this? May I suggest doing so, slowly. You have a wonderful chance to observe and study each other at a distance. See how he interacts with others, with those in power and those of humbler status. How does he respond to stressful situations? In summary, consider proceeding only when it is permissible and desired.