Secretly dating my boss

Especially if you’re that rare breed of relatively attractive cubicle dweller under the age of 40 -- aka “office hot.” You’re smart, so you already know this is a beyond horrible idea, but after the fourth or fifth round at happy hour, you literally give zero fucks, and what’s the big deal if you hook up, it’s just sex, amirite?? The less you interact at the office, the more you’re going to want to do all sorts of dirty things to each other later. It’s also totally hot to steal a kiss in the break room when no one else is watching. On a scale of 1 to worst possible decision you could make, this hovers somewhere around the worst possible decision you could make. There are ways to make this work so that neither of you end up on the wrong end of a lawsuit and/or at the unemployment office. At least until you are entirely sure that this is going to be a lasting relationship and not just some sort of taboo “sex-on-desk” fantasy that you both need to get out of your systems.

But try not to be too cavalier in case, you know, you get fired. If you do decide this is legit, there are ways to maneuver, but you’re both going to have to learn to be flexible and tolerate a lot of bullshit. They will claim you get the special treatment, even if that is entirely untrue. A lunch here and there is fine, but limit the amount of times you are in his or her office alone with the door shut, even if it is strictly business. Quitting with dignity so you can screw in sweet private bliss is also a valid option. Hopefully your friend isn’t all murderous about that whole wanting to bang (er, “date”) his sister thing, but all other examples set forth by our nation’s forebrothers show that charting these choppy waters isn’t easy.

I said don't insult my intelligence and walked away.

I am afraid he may have told the VP I found out about them and that she may try to get rid of me. She is a cold, ruthless woman and very capable of finding some reason to get me fired.

I then later saw him and somewhat joked about him and the boss.

He denied [they were having a relationship], said I was getting carried away and that I should not be reading private documents.

Sarah, a 30-year-old graphic designer, met Matt through a colleague at the imaging tech company where they both worked.

"I didn't really notice him at first because he had a beard, and beards weren't my thing," she says.

As you will still have to work together these hurt feelings can make it very uncomfortable for everyone.

If your boss is the one feeling hurt or rejected they could make your life intolerable or maybe even find a reason to fire you.

I explained that all scanned-in docs are not named and you have to open all the docs to find your own doc.

He said the real estate deal did not go through and that it proved nothing.

Plus, the less people know or suspect at work, then the less awkward it will be when you inevitably break up. Bottom line: this is still your place of work, and should things toe the line between professional and unprofessional, you will have HR and fellow employees on. You’ll have more luck if your feelings actually do extend beyond wanting to do it in the guest room at the family BBQ.

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