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I Am Secretly Dating My Boss

Dear Sugar
I recently started hooking up with a co-worker of mine and so far so good. Actually, I don't even know why I am sugar coating it, truthfully, he is my boss. Out of the office, he is everything I have ever wanted in a boyfriend, but when we are at work, it's a hi, bye, and the occasional smile and wink. Our relationship must be kept at a low profile for obvious reasons, but are his actions at work any indication of how he really feels about me?

Over the past few months, my feelings for him have escalated. I am trying to play it cool when we are together, but I think he is catching on. He sends me what I think are flirtatious messages, but I can't tell what they mean since he is so cold to me at the office. Our dates are always very romantic but I have no idea what his intentions are. Am I setting myself up for heartbreak? Will this ever be more than an out-of-office fling? Hopeful Heidi

To see DEARSUGAR's answer

Dear Hopeful Heidi
Office romances are often very complicated, especially if he is your boss. Is inter-office dating allowed at your company? Are either one of your jobs on the line? Do you want to make a commitment with this man if he is willing?

Being coy at work might be best under the circumstances, since you don't want people talking thinking that you are just looking for an easy leg up. I think the best thing to do is be open with your feelings if you want to pursue this relationship.

Since you have been dating for several months, it is about time you have a discussion about the status of your relationship. Find out if his flirtatious hints are advances or just friendly acts in passing. The only way to find out if your relationship will ever be more than an office romance is to confront him about it. This could be an uncomfortable discussion since you report to this man, but it is the only way to get answers you need to satisfy your curiosity.

If you get the response you are looking for, hopefully you can feel more secure with your demure work day exchanges. If he is not ready to make the commitment you are expecting, it might be best to cool down the office heat. I hope everything works out for you.

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