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Ask B. Scott: ‘I’m Secretly Dating My Boss!’

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Dear B. Scott,

I’m a 33 year old woman and I work in a corporate environment. I’ve recently entered into a relationship with the CFO of our company. I know that sounds weird, but hear me out. He’s single (divorced), attractive, he makes GREAT money, and we genuinely like each other.

The problem is that my friends (more specifically my coworkers) and CEO don’t really know what’s going on and I don’t know how or if I should tell them. It’s really none of their business, but as things are starting to get more serious between myself and “John”, I don’t know how much longer I can keep them in the dark.

Our work environment is situated to where we don’t see each other in the office except for the occasional meeting, but I’ve made more than a few “appointments” with his secretary to “talk”.

Can you offer any advice as to how to handle the situation? Should I talk to him about it first? I don’t like keeping secrets, and this is starting to become a big one.

Dear love muffin,

The beauty of love is that you never know where or when you may find it — or when it may find you!

It’s refreshing to hear that you’re involved with a single man, because many of my love muffins in similar situations write in saying the exact opposite!

Now, I don’t think there’s anything wrong with keeping your friends in the dark while you figure out if and how things are going to progress. However, if you two decide that you have genuine feelings and wish to pursue a healthy relationship then at some point the secrets have to stop.

I’m not saying you have to declare it publicly, but you should feel comfortable enough to stop taking those extra precautions in order to keep things “hush hush”. As with anything, you should never feel like you have to lie to be happy.

I would talk to “John” and let him know your concerns, because you can truly only go public if you both agree to do so. Once you’re ready to open up about your relationship, start with the people closest to you. However, try to keep it on a “need to know” basis.

The last thing you want is to be the center of office gossip. Plus, relationships tend to last longer when everybody doesn’t know your business.

Love,

B. Scott

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