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Ask Dr. Sherry: I’m Dating My Boss and He’s Cheating With a Co-Worker

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Dr Sherry Profile Two

You've seen celebrity clinical psychologist Dr. Sherry Blake, author of The Single Married Woman: True Stories of Why Women Feel All Alone in Their Marriages, keep the Braxton sisters calm on the hit show Braxton Family Values. Now it's your turn to sit in her chair...

Q: I need your advice for the problem I'm facing now. I've been dating my boss for nearly a year and we agree to hide our relationship from our colleagues because we want to avoid any gossip that might affect our working environment. Fortunately, both of us can separate our personal and professional relationship. Well, until now.

He is a nice man and he likes to flirt with the girls in the office. He does it jokingly, but unfortunately, many people misunderstand his gestures. They think that he's falling in love with them. Right now, the real problem is with his assistant. She and my boyfriend are very close professionally and personally. One day, I accidentally read their messages, and I found out that their relationship has become more than just friendly. She was admitting that they are dating each other. At that time, I told my boyfriend about this and asked him to let me out of his life if he really likes his assistant.

He insisted on maintaining our relationship and convinced me that the messages were only romantic words, which meant nothing to him because he was just being nice to her. He told me that she must have just misunderstood. I know that she has a tough life and she is a lonely girl. I just thought that she might need someone who can be there for her and she found it in my boyfriend and therefore considered him her boyfriend too. Either way, this matter is still annoying me and I cannot control my heart and my mind every time I see them together. She doesn’t know that he is my boyfriend, and she always tells me stories about what happened between both of them and even sometimes asks me for some advice. I'm trying to be neutral, and not say too much, because I just want to be fair to both of them. It really breaks my heart and it’s distracting.

My boyfriend knows about how I feel and always convinces me that he loves me and will not cheat on me. My heart says that I can trust him. Please, tell me what I should do. How I can control my jealousy? Should I still trust him? I would really appreciate for your help. Thank you!

Best Regards,
Anonymous

A:
My dear, please tell me you aren’t really serious? Anytime you decide to date someone at your job, especially your boss, you are starting out on shaky ground. Do you really believe you are the very first, or the only, woman he has dated at the office? Do you really believe that his assistant is “only a friend,” and not just another girlfriend? The office is clearly his playground and you have just been taken for a ride. It is time to stop the merry-go-round and get off. Stop making excuses for him and his assistant. Unfortunately, it is what it is. Your boss has been "playing" you and you have been a willing participant. As you mentioned in your note, your boss is known for his flirtatious personality and being a “nice” guy who obviously does not mind crossing boundaries with you or anyone else at the office.

He has not only disrespected you and your relationship with him by having a relationship with his assistant, but he has protected himself and his flirty habits by getting you to somehow agree to keep his secrets for him. I would not be surprised that your secret relationship with him is a well-known "secret" in the office too. You have been blinded by your feelings for this man. Now that you see what you are dealing with, the choice is ultimately yours.

You can continue with your relationship with him and pretend you are the only woman in his life or you can wake up, see him for what he is, let it go and move on with your life. I highly suggest that you decide that you deserve more from a man and a relationship. The writing is on the wall, now it is up to you to read it. – Dr. Sherry

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