AdviceSex and Dating

Sex & Dating at Work

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The departure of Don Draper’s secretary, Allison, that we could see coming from a million miles away on the latest episode of Mad Men got me thinking about how horrifying it would be to date or have relations with someone at work. I say it’s probably best to avoid it all together, but if you MUST, here are some dos and don’ts (mostly don’ts) you might want to consider:

1) Don’t date someone with a significant power difference from you

You think dating someone of a different sex can be hard because of power differences? Well, dating your boss or your assistant is probably about 10 billion times worse. The thought of being obligated to do what the person you’re sleeping with says makes me sick, as it opens the door to all kinds of respect problems. At least if you’re dating someone at your job level, the awkwardness will just lie in seeing them.

2) Don’t work directly under someone you’re attracted to

Not only will sleeping or dating your boss mess with respect levels in the relationship itself, but it will completely fuck up your work dynamic. It’s tough to even be friends with your boss while trying to maintain professionalism while at work, but sleeping with them dictates a level of intimacy that is almost impossible to pretend never happened.

3) Do quit right away

I’m not entirely sure why Allison didn’t type up a resignation letter right after Don gave her that shitty bonus, but if you feel completely disrespected or incredibly uncomfortable at your job, just quit. There’s no way you can un-do someone being shitty to you after sleeping with them. And I would add that even if it IS Don Draper, the fact that he can’t even be bothered to take off his pants or shirt while having sex with you is probably a bad sign.

4) Don’t bring stuff to your boss after hours

After hours anything is kind of scary, because it’s a gray area. Technically, you’re not on the job, but you can’t just act however you want. Just don’t bring Don his keys. It’s not your responsibility.

5) Don’t stand for sexual harassment

Yeah, it’s a pain in the ass to complain. Yeah, you don’t want to deal with it more than you already are. But, you know what? Nothing will change and people will continue to be under the radar if you remain complacent or silent. Why should you have to be made to feel uncomfortable just because some asshole wants to wave his dick around? Fuck that. No one has the right to make you feel threatened or uncomfortable on a daily basis, and there is no reason to tolerate it. Call their ass out even if it doesn’t make a difference. At least you’re letting them know that YOU know.

6) No one you sleep or have an affair with is ever secret

Face it, no matter how much you trust yourself or the other person, your “secret” will be out. It’s inevitable. Always.

7) Don’t sleep with or date a notorious womanizer and expect them to treat you well

I know it seems crazy, and people seem to have ego issues with this, but no one is going to change their whole personality for you. Or change their personality in general. You’re beating a dead horse and setting yourself up to be fucked…in the bad kind of way.

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Anna G - Caliburg Contributor

Anna G - Caliburg Contributor

Anna G. is a Southern California native living in the Williamsburg area of Brooklyn since 2005. Anna is constantly trying to unite her love of CA sunshine and the excitement of the New York urban jungle, all the while trying to keep her unwieldy credit card debt under control, and look fabulous at brunch, no matter how un-showered and hungover.