I’ve got a crush on the boss. Should I make a move?

Dear Aunty B,

You’re the only one I can talk to here. My boss is a wonderful woman who has got divorced about two years ago.

We’ve been working together closely and I’ve developed strong feelings for her. We travel a lot together, we share meals a lot together, we think in a similar way. I think she has feelings for me too but I can’t be 100% sure.

I’d really like to try and take the relationship to a new level, but I know it’s complicated beyond belief.

Should I act on my feelings, Aunty? It’s eating me up inside…




Dear Lovelorn,

Car crash alert! Car crash alert! Car crash alert!

You’re affection for your boss is touching, but I think pursuing this relationship is a very, very bad idea.

While there are examples of (mainly male) bosses marrying their employees, I reckon these are the exception rather than the rule.

The way you are “close” to a work colleague is very different from the way you are “close” to people outside work. So you share a few meals and plane rides and spend lots of time in meetings together – you’d be doing this if your boss was a man or a woman or a Martian.

Think about it. Do you really know that much about this woman? Do you know anything of her interests and passions outside work? Or are you just seeing one side of her.

I think you’ve got to let this one go, Lovelorn. It could turn into the romance of a lifetime, but it could also be an absolute disaster that hurts both of you and the business.

Be smart,

Your Aunty B

Email your questions, problems and issues to auntyb@smartcompany.com.au right now!


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