98.3 TRY Social Dilemma: Should the Office Know if You’re Dating Your Boss?


ALBANY, N.Y. (NEWS10) – Today’s 98.3 TRY Social Dilemma came from Lily and it’s about dating. Here’s her email: 

Hi Jaime. I have a bit of a dilemma. I started dating my boss back in November and no one knows. It’s not against company policy, but it would be frowned upon. We care about each other and have been having a lot of fun! My friends are having a big post Christmas get together this weekend and I want to bring him, but he doesn’t think he should come. He’s afraid someone at work will see a picture of us together and he thinks for now we need to keep it hush. I told him we should just go public with our relationship but he’s being weird about it. He thinks it will make me look bad, and he says he doesn’t want my reputation ruined. I am proud of our relationship and I want to show off my guy! Is it a red flag that he doesn’t want to go public with our relationship, or does he have a point? Thanks so much Jaime…Happy New Year

~ Lily

Well, this is a tough one. I know dating your boss can be difficult. If it all works out, it’s great, but if it doesn’t, that can lead to drama. But I’m guessing that both Lily and her boss are adults who could handle it. And I understand her boss’s feelings but at this point, I think it should be out in the open. Especially at work. In my experience, people can figure those things out anyway, so better to be honest. That’s just my take.

What do you think? let’s help Lily out and let me know on the TRY Facebook page

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