11 Truths You Should Know Before Dating Your Boss

Two years ago today I made a horrible, no good, very bad decision. I was a dirty bird who fouled my own nest. Dipped my pen in the company ink. Messed around with the help. Or I guess he did…Whatever, I’ll speak plainly, I made out with my boss. You have to understand. It was an incredibly romantic setting. I couldn’t help myself.

Our hands were full of plastic spoons as we prepared for a midnight showing of The Room. (The most romantic movie of all time.) He had given me a thoroughly confusing multiple choice quiz wherein he stealthily asked if I had a crush on him. And then offered to hook me up with someone else in the office when he thought I had answered incorrectly (I hadn’t). Plus, we were in the parking lot of a Rainbow Foods. How could I resist?

And don’t think I didn’t try. I very loudly proclaimed “but, you’re my boss!!!” between smooches. It was magical. I was essentially living in the Katherine Heigl movie of my dreams.

For the sake brevity, I’ll skip the will-they-won’t-they part of the movie to the part where I’m actually dating my boss. Officially. Well, officially everywhere but work. And I have to say I was damn good at it.

We made it through weekly staff meetings, numerous happy hours, 6 months of dating, one of us finding a new job, a one-year anniversary, our engagement, and finally the other finding a job before anyone at work found out. And even then it was only because we had decided we could maybe let our coworkers know I was dating my boss. Because, by that time, none of them were actually our coworkers anymore.

To be fair, we probably weren’t as awesome at being discreet so much as our coworkers were relatively clueless, didn’t care about our personal lives, or were too wrapped up in the other interoffice relationship shenanigans (the ones that made no effort to be surreptitious). Seriously. That place was like a private Lutheran college. People went in single and came out with advanced M.R.S. degrees. A fact, that probably made it relatively easy for us to fly under the radar as one of the many relationships.

That being said, my experience has equipped me to offer up  plenty of unsolicited advice should you decide you want to follow in my inadvisable footsteps and date your very own boss. You’re welcome.

1. You Will Bring Work Anger Home Even Though You Shouldn’t

Even if you don’t work with your smooch-er-oo, very wise people advise that you leave work stress at work. Those very wise people have never worked. Because it is damn near impossible to forget all the dumb shit that Kelly in HR said today. It’s just a microwave, Kelly! We don’t need a Gantt chart to determine the daily lunch process. Calm down.

When you date your boss, it will become even more imperativeand more difficultto leave work tension at work. So just accept it. Explode in a respectful way about how you know how to right click, but the program is obviously broken! And then move on. You’re human and you’re both going to get a little worked up about stupid work stuff that doesn’t matter.

2. There is Going to Be a Bit of a Power Struggle

Some of that stupid work stuff will be a direct result of this weird power dynamic. In your relationship, you are equals. Or you better be. If you’re not, run for the hills, sweetie. At work, (s)he’s the boss, and you have to respect that and you’re going to hate it.

If you run into tension as a result of the power struggle, the best thing to do is return the balance of power. This can be done through withholding affection and cold stares.


3. Not Everyone Will Be As Oblivious As Our Coworkers

I don’t know what was wrong with our coworkers, but I think it’s a good thing they started administering weird IQ tests after we parted ways with the company. There were a few people who speculated that something might be going on, right before they left the company, so maybe there was a bubble of naivete that surrounded the whole building. Whatever our luck was, you can’t expect that yours will be the same, so be prepared for that.

4. A Sudden Change in Behavior will Raise Eyebrows

Just because you’re paranoid doesn’t mean they’re not after you, my friend. But if you act like you’re paranoid and they aren’t, in fact, onto you, they will be soon. No carpooling, happy hour tab sharing, or talking about shared weekend adventures, you fools!

Don’t go the opposite way either, if you were flirty before, don’t just go cold.  But don’t take the flirting overboard and start touching each other at work. Unless it’s in the supply closet. It’s a delicate balance to master, but I have faith in you.

5. You’re Going To Have to Fib

Your coworkers are probably going to ask about your personal life. Because they are nosey little miscreants who want to know if they should harbor jealousy or pity you. I say, play them from both sides. One of you make up stories about the hot barista you’re seeing. The other can pretend you’re simply too scarred by your previous relationship to move on. The latter tactic often comes with the bonus effect of getting people to avoid you completely because no one wants to be around some sad panda all the time.

6. It’s Best if You Live Somewhere Larger Than a Teacup

Minneapolis is not exactly a hamlet, but it was almost too small to pull the boss-dating maneuver. We had a couple near misses where we’d find out on Monday that we were steps away from getting caught at some bar, restaurant or festival over the weekend. To be extra safe, embrace the old married life prematurely and refuse to do anything more than binge watch Netflix from the safety of your couch. And make sure you close the shades.

7. You Need to Stay the Hell Off of Social media

This could be simple. If your friends weren’t post-happy idiots who will not rest until they’ve tagged every person who attended their birthday party. Explain to these needy individuals nicely, but firmly, that their ego trip will destroy your career, relationship and probably life. If they’re perfectly willing to take that risk for the sake of the guise of popularity, post that one drunk you’ve been saving since Laura’s bachelorette party. They’ll get the hint.

8. This book will be completely useless to you

9. There Will Be Moments When You’ll Want to Do Murder as You Silently Witness Someone Else Flirting With Them

This was not a frequent issue, but when it came up for us, it was miserable. Maybe it’s a fellow coworker who is miserable in her marriage and needs an outlet. Maybe it’s the lithe new intern who is impressed by a dude who pays his own credit card bills. Maybe it’s the overly friendly harlot concierge at your convention hotel. Just hold your tongue and use the tactics in number two when you’re alone. Or talk it out like adults and make him tell you you’re pretty. That works, too.


10. Knowing You Aren’t Going to Be There Forever Helps

If at all possible, only fall in love with your boss when you aren’t in love with your job. It makes the “What ifs” easier to answer. I found a better position before we had to navigate annual reviews, raise negotiations, shared vacation time and inviting coworkers to a surprise wedding where the surprise was that their two single coworkers were the bride and groom. I have to imagine it also makes it easier to cut your boss loose when he tries to implement annual reviews and raise negotiations in your relationship.

11. You Probably Shouldn’t Break Up

I found the best way to date your boss without any major complications was to marry him. It simplifies matters and minimizes the potential for awkward encounters after you return his toothbrush. It also white washes the weird stigma that follows a girl who dated her boss. I’m banking on that last one so I hope it proves to be true. Otherwise going public with this post was a horrible mistake.