Sex at Work – That’s a Hard One


Longtime reader, first time writer!  I am frustrated and conflicted so please give me great advice because I need it!

In a nutshell: I want to have sex with/date my boss Ted.  We are both single and the attraction between us is undeniable and intense.

This is bad, because I both need and love this job.  I have a challenging position at an awesome company and I spent years getting where I am.  I also have a child from a former relationship to support so losing my job would be catastrophic (his dad isn’t in the picture).

We have flirted and sidestepped around the issue for months but over drinks a few days ago he told me he feels the same way.  He promised he would never do anything to jeopardize my position and I want to believe him but I don’t want to do something stupid and naive.  He thinks we can keep this on the down-low.

I told him I’d give him an answer to his invite for dinner after I consulted with my shrink – which is you.  Ha ha.

Seriously, what should I do?


Dear Swooning:

Listen up, gurl: there’s the good kind of getting fucked by your boss and the bad kind.  Unfortunately, often the twain shall meet.

Happily for you, in this day and age when the shit comes down it usually comes down on the head of whomever in the relationship held the highest corporate rank, especially when the subordinate/Sexytime Friend is a direct report.

To the contrary, for Ted this means that no matter how much he can prove you freely consented to his boy being in your boat, he is at risk of both legal liability and job loss.  

I would give him advice too but I won’t work through a proxy, so please have him contact me if he would like my take on his side of this dilemma because the risks for Ted far outweigh yours.

Advice for Swooning:

1. Tread carefully and ask yourself: 

If things go wrong, and I mean Glenn-Close-in-the-bathtub-with-a-knife wrong, can I still work with this guy?

In order to make this assessment I suggest you picture the last man in your life with whom you had a terrible breakup. Could you work with him, or would you be so busy planning how to get antifreeze into his latte every morning that your project list would suffer?

2. While you’re at it, answer this:

Am I willing to be seen as “that type” of woman – the type that bangs her boss to get ahead?  Am I willing to have my accomplishments and acknowledgments constantly questioned because people know I am sleeping with the boss?  

How will that affect my professional reputation both at this company and going forward if I want to take a (non-sexual) position in another organization?

3. Don’t kid yourself.  

You can’t keep this on the down-low.  If the magnetism between you and Ted is as intense as you say and you are already out having drinks together, you’re both likely the subject of office gossip, so he better be sponge-worthy.  That leads me to #4:

4. Find out what your corporate policy is on fucking up and down the chain of command, otherwise known as “personal relationships between subordinates and the people who get paid much more for taking credit for their work.” 

If this is a big no-no at your organization, I strongly suggest you find another Russell the Wonder Muscle to occupy your lady bits.  If there is no specific prohibitions against Ted pulling his Trouser Tank into Fort Bushy and you just can’t resist, go for it.  

But don’t say I didn’t warn you, because interpersonal relationships at work can be poisonous, even when they are just friendships.  I long ago made it a personal policy to neither copulate nor become friends with people at work because it bit me in the ass, literally and figuratively, each and every time.  

It’s probably for the best that I now work alone.








This Post Has 3 Comments

  1. Agree!

    Oh yes. Been there DONE that. Big mistake. It never ends well.

  2. Keith Stone

    I like the piece in here about friendships-tough because the workplace seems to be where people make the most friends…. great advice Robin!

  3. Arakasi

    I saw this happen at a previous job I had. He was married, she wasn’t. There had been rumours in the office that there was something going on. Things came to a head when someone forwarded pictures from the company Christmas party to his wife. The wife met him in the driveway with a shotgun.

    He survived with minor injuries, but the mention in the newspaper made it impossible for the company to ignore. Since the two didn’t technically violate the dating policy (he was senior to her, but not in the direct chain of command), neither was fired. She was, however, transfered to a different job in a different office in a different state.

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