Advice Column

Dear Miss Olivia:

     I am thinking about having an affair with my married boss.  I know one’s not supposed to do that sort of thing, but I have never been this attracted to anyone before and he feels the same way.  I believe that we might actually have a future together.  What should I do?

     The Other Woman (Maybe) in Seattle

Dear Other Woman:

Here’s what you need to know about sleeping with your married boss…

There won’t actually be any sleeping going on; at least not in the literal sense.  He will always have a meeting to go to, a wife to get home to, or a kid with a game/practice/recital/play that he promised to go to.  As soon as he’s done having his way with you, he’ll be out the door.

You cannot be anything like his wife is in bed.  If he was interested in what she had to offer, he wouldn’t be doing it with you, now would he?  Therefore, be prepared for amateur porn star hour.  At first, you will find it flattering that he wants to ravish you so feverishly, but after awhile you’ll come to realize that he’d do the same things to just about any other woman if she were willing; you just happened to be the first to sign up.

It will help to have a psychology book of some sort on hand as well because he will undoubtedly dump all of his problems on you.  His wife doesn’t understand him, his own boss is a jerk, he hasn’t fulfilled any of his childhood dreams…there will be many complaints and you will be expected to say all the right things at just the right time.  Don’t share any of your feelings with him, though.  He gets enough whining from his wife; he doesn’t need to hear it from you, too.

He will never, ever leave his wife for you.  He might tell you that he wants to, but he will always come up with an excuse for putting it off.  Even if he did…well, if he’s willing to walk out on the mother of his children then he’ll have no problem tossing you once the bloom is off the rose.

You will also need to keep one of your platonic guy friends on standby at all times because you certainly won’t be able to bring your married boss as your date to the company Christmas party.

This secret relationship of yours?  You will need to keep it a secret.  This is real life we’re talking about, not some overrated Sarah Jessica Parker television show where an extramarital affair is okay if it lands you Chris Noth in the end.  Your friends will think you’re a floozy, your family will think you’re a floozy, and your coworkers will think you’re a floozy if they ever find out.

Sadly, your friends and family and coworkers will eventually find out, even if you do wisely keep your mouth shut, and they will finally see you for what you really are: a floozy.

The only thing worse than a floozy, of course, is a floozy without the foresight to know that the fling will eventually come to an end.  When that day arrives, you had better have a plan to carry you through your inevitable unemployment.

For example, I sued my former workplace for one hundred thousand dollars when my boss fired me two weeks after I dumped him.  That gave me all the money I needed to establish this little advice column of mine.

Now that I think about it, fooling around with my boss may have been the smartest thing I ever did.  But you know, to each their own.  Let me know how it works out for you!

Miss Olivia


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