Why Dating Your Boss is a Terrible Idea that Ends in Ice Cream

“My boss* is handsome, responsible, smells good, is my age, and we should probably date!!”

Ok, while that clearly sounds like a great idea that would definitely not cause any problems in any area of your life ever, it’s not. I’d rather not say that I fell into this handsome trap of a situation, but I did. (Ok, I didn’t “fall” into it as much as I stared longingly into its eyes…) Along the same bad idea vein as dating your boss is writing a public blog post about dating your boss, but I will be sure to at least make one good decision and post it after one of us is no longer working with/under/over the other.

EDIT: Ok, the proper amount of time has passed, jobs have changed, and he is still wonderfully handsome (whew!)

There are many reasons to not date your boss other than that tiny “against company policy” thing. I will outline six such problems now:

1.       It has to be a secret. Secrets are horrible and I believe they put holes in your brain and increase the likelihood of embarrassing sleep drool. This secret won’t be a total secret because if things are going well others will notice that stupid twinkle in your eyes and then confront you about the stupid twinkle, in which case you will have to deny it. You deny it in a few ways: Laugh, try not to blush, tell the other person they're dumb, and then make confusing sounds asking random questions in hopes of diverting the conversation:    

“PPPpfffttt,wha? Why would? Naaaahhhh, I mean he’s dumb, kinda. Thhhppppfffttt, *sigh*, *yawn* Hey did you just fart? My mom’s calling me; gotta go!”

They’ll be totally confused and werided out, probably offended, but not convinced. Another logical reaction would be to fly off the handle over the “rumors”:

 “What the hell! This is insane!! I do not have time for you people to be spreading rumors about me!! THIS IS SERIOUS I COULD LOSE MY JOB! I HAVE BILLS AND I RUN A SHELTER FOR ABANDONED BLIND ENDANGERED OWLS AND I NEED THIS JOB OR ALL THE OWLS WILL DIE!! YOU…YOU… OWL KILLERS!”

2.       Conversations will either center around work, or be nonexistent. If you work together all the time your stories will always be the other person’s stories too. So you can go on a date and dinner will sound like this:

 “Hey remember when Betty did that thing?”
 “Yeah.”
 “That was funny.”
 “Yep.”
"More hummus?"

Or you will order food and have nothing else to say because you spent every moment of everyday together doing the same things and you will be suuuper uninteresting to the other person. Or you could always talk about the schedule.

Yeah.

 That’s fun.

 The schedule.

3.       Your boss will not want your advice on how to be a better boss. In fact, he/she will hate that. A lot. Explaining to him/her how they could’ve handled that one situation better is a terriblehorrible idea. Even if your suggestions are really good (and they always are), they’re not.

4.       You will accidently slip into comfy mode:

 “Excuse me, respected employee that I have a completely professional relationship with in every way, could you hand me the calculator?”

and at some point you will inevitably say,

“Here you go my snug-a-saur.”

You will then both freeze as if your co-workers are T-Rexes who will move on if you just stay still long enough.

5.       If you are in a relationship with your boss I hope it is a temporary job that is of relatively low importance to at least one of you. In fact, it should be a job that isn’t even worth putting on a resume. For me, my job was a part time hostess position while I was in graduate school. I needed money and a flexible schedule. This was not my career path, and I wasn’t staying long. It is much worse and more detrimental to your life, in my opinion, if you decide to have a relationship with your CEO in a career where you have a 401k . Those types of jobs are serious about their policies and you will both be terminated. It might even be labeled a scandal. Scandals are only interesting if they do not involve you in any way. Especially in any sexual way that will inevitably involve a video camera or recorded conversations. It is a scandal after all and no one can resist wanting to see you and the CEO doing it by the fax machine while you scream, “I’ll run the numbers; I’ll run the NUMBERS!”

6.       Your relationship with your boss might prove beneficial for you on the job, but if it doesn’t you may be in for a worse time than you bargained for. If your boss/significant is set on not treating you any different than anyone else at work that may unfortunately morph into treating you worse than anyone else at work. This is, of course, because of the paranoia that someone may think you’re getting special treatment. If you want special treatment keep it in the flirting stage. If you’re flirting there’s nothing to hide, so no paranoia. He/she will treat you special and have no qualms about doing so because it’s just a crush with nothing to tell. The moment you slip past that he/she may need to prove there’s nothing going on, because there is, and therefore your coworkers will say “Wow, he/she’s really mean to you” “He/she yells at you the most” “What’s his/her problem with you?” And that, my friends, hurts because you know he/she isn’t like that. Right? They’re not. Not really anyway. Wait, why does he/she hate me the most. All I do is try to help…. And THAT is where you will drive you and significant insane. You will fight and yell when there would be no reason to fight or yell if you didn't work together.

So, there you go, you should just quit now. Thankfully for me I happen to be worth putting up with and so is he.

ADDITIONAL EDIT: We now work in two completely different fields with completely different hours and most of our time is now snuggle / feed each other ice cream time. Yes. Hooray for snuggle time. Snuggle time with kittens and pugs…and ice cream. So much ice cream.

*NOT the same boss as the one in “A Post Post About the Boss Boss.” Not. Even. Close.