Ask EDN Question:

I work for a startup in the Bay and I’ve been there a year and a half. For the past 10 months my boss and I flirt with each other a lot. He’s cute, charming and smart and although he’s not Eritrean, I wouldn’t mind if he put a ring on it. Colleagues have asked me if we are together but I say no and keep it pushing. My company is very young and playful and there are other folks who do the same thing, I’m just flirting with the boss. People say I’m treated differently, but I don’t think I am although sometimes he’ll bring me coffee in the morning or lets me slide when I’m late. In general no one gets in trouble for being a few minutes late. My team will go to Happy Hour sometimes and normally he and I will stay and hang out after everyone leaves and talk. He’ll also texts me when we aren’t working about stuff that has nothing to do with work but nothing physical has occurred other than hugging.

I mentioned this to my older cousin the other day and told her that I may have a crush on him and she was in shock. She said my relationship with him was inappropriate and that I need better boundaries. I disagree but since you guys have ask EDN I figured I would ask. Is my relationship with my boss inappropriate?

Response:

Thank you for your question! Office romances and flirting in the workplace can be very tricky and have potential negative consequences. After posting this question on our social media platforms and discussing it here at “Ask EDN”, we feel that this relationship could cause more harm than good.

A first step in navigating this tricky relationship with your boss is to consult any office policies on dating. Many companies have policies in place related to dating in the workplace, and these policies tend to be especially stringent when power differentials are at play (which is the case in your situation). Be sure to check with HR if there are any policies at your company regarding dating and if so, you should follow those policies. We understand that at this point, you and your boss are flirting and not in a relationship, but it sounds like it has the potential to go that route, so it would be important to be proactive in establishing boundaries based on company policies.

You should also consider the risks involved in continuing down this flirtatious path with your boss. First, as mentioned above, there are power differentials between you and your boss and this can result in a conflict of interest. You could receive or can be perceived as receiving preferential treatment (which seems to be the case already) and this can cause a strain between you and your colleagues. If you and your boss’ relationship ends (badly) or fizzles out, there is also the potential that your work life could suffer- including awkwardness in the office, a stressful work environment, and resentment from your boss leading you to potentially miss out on promotions or other opportunities for advancement.

Flirting with and dating your boss comes with many risks. However, not all is loss with pursuing a relationship with this individual. You should have a talk with your boss and see if there are mutual feelings of pursuing a relationship beyond the flirting. If so, you should talk to HR about dating policies. If there are no policies in place, you both should discuss boundaries and behavior in the workplace and a plan for how you will handle your relationship (e.g., keep it private, transferring to separate departments, potential breakup, etc.).

Ultimately, only you can judge if the risks associated with flirting and a relationship with your boss are worth taking. When assessing which direction to take, be sure to consider the pros and cons to both your personal and professional life.

Wishing you all the best!

EDN PD