Sleeping With The Boss: Career-Ender?

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Sent in by Ms. Jennifer C.
April 28, 2008 @ 03:11 pm


Dear Matt-
I slept with my boss. He is just a few years older than me and it happened one night after we all went out. But, now I feel sooo weird around the office and I have no idea what he is thinking? Should I say something to him about it?  He has yet to bring it up.

Sleeping with the boss could almost be like sleeping with the enemy, find out how to make sure it doesn’t ruin your career.
It’s not the easiest of situations. You were out late, your boss was among the group and somehow you ended up in bed with him. Now, he won’t stop calling because he wants to hook up again. Is is a career ender?  These troubled waters are always better left uncharted; but since you are already in the eye of the storm, we will try to throw you a couple of lifelines. Your body has gotten you into enough trouble, now you have to start using your mind.
That said, the “It” girl can put it all together; and believe us, she does! Use your imagination, and we’re not talking about contrived and boring 5-Star dinners or planned, stressful trips to the Caribbean Islands. Little sexy episodes spread throughout the week, are much easier and never forgotten.

For more advice on this sometimes crazy and confusing world of dating, check out: Why Hasn’t He Called?

1. Flattery in this case will get you everywhere. Tell him that you could easily fall for him, but you can’t possibly risk both of your jobs because you tend to go a little “love crazy”.
2. Scare him overboard and tell him that you are ready for a family, and you are thrilled that with him, you have the right guy (him), to start planning it.
3. Threaten mutiny and tell him that you feel like you have to tell a couple close co-workers your feelings because you’re confused and need a little clarity.

These suggestions might help your boss realize that he might not be ready to go down with the ship quite yet.

For more advice on this sometime crazy and confusing world of dating, check out: Why Hasn’t He Called? This book will be out January 13, 2008. It in, my wife and I answer that age-old question, Why Hasn’t He Called? and provide all the answers you will ever need to navigate the crazy and confusing world of dating!


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