Carefrontation

My boss has a fiancée who doesn’t know he has another girlfriend. I don’t know whether or not I should say something to one of these women. I like his fiancée. The other woman is sleazy. My boss tells me that she’s just a friend but she hangs all over him when she comes by the office. She also drops sexual innuendos as if she wants me to know that they’re more than friends. I feel sorry for his fiancée, who is a sweet person but maybe too trusting. Should I say something? I don’t think I would get fired if my boss found out that I talked to his fiancée because he and I are good friends. Advice?

Strip your vocabulary naked. Your boss doesn’t have a girlfriend. He’s cheating on his fiancée—unless they have an open relationship and haven’t announced it to the world. Since you are friends with him, have a chat, preferably away from the office. Let him know you’re worried about him because he’s engaged to be married yet appears to have a friend with benefits. Admit that you’re operating on assumptions. State clearly that you are uncertain whether your perceptions are real. Ask him to speak to his friend about maintaining a more professional demeanor when she visits the office. If he’s not in an open relationship, push the carefrontation (yes, you read that correctly). Tell him how much you like his fiancée, and say that if you were in her place, you would want someone to clue you in if your man was cheating. Explain you do not wish to appear complicit in his deceit. Say it’s his job to confess to his fiancée, and not your job to out him (at least not yet). Then give your boss a few days to reflect. One last thing: don’t delay this conversation. Friends don’t let friends create chaos in their lives.

How does a person know when to set a boundary? I’m assertive, but it’s hard for me to set boundaries with men. Why don’t people just avoid doing things that could lead to making me (or them or the situation) uncomfortable? So irritating!

We set boundaries as reminders that we deserve to be treated with respect and to protect ourselves when we feel unsafe. Boundary violations often result from our own inconsistency in maintaining boundaries. So ask yourself: Do I over share before I know a man, and then overreact when he doesn’t respond as expected? Do I hook up before I know whether a man is emotionally available or whether he’s hostile and wounded? Do I honor my own boundaries? Part of adulting is growing to understand that people learn how to treat us by observing how we treat ourselves. Refresh here: A boundary defines where you end and another person begins. Trying to force intimacy (emotional, spiritual, physical, or mental) with a man before it might unfold naturally creates uncomfortable situations. Want less drama? Let intimacy develop slowly over time.