I kissed my boss at the holiday party and I have felt uncomfortable with him ever since. We have always gotten along well and both are single. But, neither of us has spoken about the incident since it happened. Should I try and bring it up to him or do you think he just wants it to be a one-time deal since he has not said anything to me?
Kissed and Confused
Dear Kissed and Confused,
Without knowing how long you have worked together and in what roles each of you hold, this is a hard question to answer. You stated that both of you are single, which makes the option to pursue a relationship a possibility if both parties are interested. You will have to talk to your boss privately and ask him what he thought about the “holiday party-kissing incident”. If he seems disinterested in talking about the kiss, take that as a clue that it was a one-time experience that is not to be repeated and move on. But if he responds genuinely sweet and potentially nervous about the incident, I suggest that you both take a chance and talk about whether there seemed to be a connection that should be pursued. If the connection is there, you will not need to force it. Just by initially starting this conversation you will be given all the clues you need in regards to his feelings on this matter. Good luck!
Kari O’Neill, MSW, LICSW, is a licensed independent clinical social worker and a resident of Issaquah Highlands.
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