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Ron Simms Jr.
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Ask MISSter Simms – I’m Dating My Married Boss

Dating My Boss

Hey, think you might leave your wife for me one day?

Dear MISSter Simms,

I met this guy at my job three years ago.  It was like love at first sight for both of us.  He says I’m the reason why he loves coming into work everyday.  He regularly compliments me, and when I’m sick he’s the first person to come and take care of me.  He’ll touch me when he’s able to; sometimes brief, almost unnoticeable contact, sometimes lingering back rubs or hand massages when no one else is around.  There’s only two problem: he’s married, and has been for a few years.  And he’s my significantly older boss.

He cares about me a lot, so much that when I tried to leave work earlier this year he asked me back as his personal assistant and gave me a raise.  I’ve tried dating other people to no avail.  Every time I meet another guy, I can’t help but think of my boss and things inevitably end before they’ve even really started.  I’m not really sure what to do at this point.  Leave work and try to move on?  Tell him that I love him and need to be with him?  But how can I do that when he’s taken and very much my senior?  I don’t want to wait forever for a man I can’t have, but what if we really are supposed to be together?

In Love With the Boss

Dear ILWB,

You probably already know this but I’m going to say it anyway: 99% of married dudes will not leave their wife for their side chick.  Divorces can be bitter, messy affairs that most people like to avoid, especially dude’s who have a ton to lose in the process.  A side chick is hardly worth all that.  If you said that he totally hated his wife and wanted nothing to do with her then that’s one thing.  But he’s been doing his thing with you for three years and they’re still together.  He’s only trying to keep you close because you’re a his escape from his wife.  I think you need to cut this relationship off as soon as humanly possible.  Sure, you could get a hell of a lot of raises from him to keep you around forever, but what about the bad stuff?  For one thing you’re wasting the best years of your life on this old man.  For another, what if his wife were to find out one day?  You could find yourself in a knife fight over a married dude, which is never a good look.  If it means switching jobs then so be it.  Just do whatever you need to do to get out of your current situation and get into one that will actually somewhere in the future.

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