by Katy Franklin.

Ladies, let me start off by saying that I am not strictly opposed to the idea of you dating your boss. Let’s make that very clear. If your boss is smart, funny, interesting, charming, perfect, single and looks exactly like Matt Damon, stop reading this article immediately and go date him!! I know I would have, had that been my situation. Unfortunately, it didn’t quite go down like that. Guys, you may, in your lifetime, come across some ruthless cougar who is also higher up than you, who will sink her claws into you, and beg you to have sex with her everyday on top of the $4000 mahogany desk in your office with a breathtaking view. If that sounds like something you may be interested in, I’ve got my fingers crossed for you. Unfortunately, my situation wasn’t quite like that either, but hopefully I can shed some light on what it was like for me when I dated my superior in the workplace.

At twenty-two years old, I moved to New York City and got a job working as a waitress at a busy chain restaurant in Times Square. Nick was my boss. Well, technically, he was my boss’ boss. While he was not conventionally hot or extremely good-looking, he was tall and had nice blue eyes, and was charming in his own way. Nick was also a player. A big-time PLAYER, and I appeared to be just his type: young, wide-eyed, innocent (enough) and at the time, I was oblivious to the fact that he had dated or tried to date every other female server, host and bartender in the place. Nevertheless, we developed a flirty and friendly relationship, and pretty soon he had asked me out on a date.

I was really nervous about going out with him, and spent the nights leading up to it talking with my roommate about whether or not this was a particularly good idea. I definitely thought about canceling on him. I mean, what if people at the restaurant found out? They undoubtedly would. Would they think I was a slut? Would anyone be jealous? I was totally going to be thought of as THAT girl who went out with her manager to get better shifts or better sections at the restaurant. But I went because curiosity got the best of me. I was interested in this person, and I told myself I didn’t care what other people thought about me.

We met for a drink before dinner and then had sushi at a little place downtown. It was semi-awkward, to say the least. I’m usually very comfortable around people, but it was a little difficult to know how to act on a date with him. We ended up talking about work quite a bit because that’s what we had in common. That, and the fact that we had both grown up in Washington D.C. He was older, had never gone to college, and had worked in the restaurant industry his whole life. I was younger, had just had all of these amazing and recent experiences in college, and had never worked in the food service industry before. Regardless, we had a pretty good time, and the date ended with a friendly hug before we got into separate cabs to go home.

Now, you might think that that was the end of it. I went on a date with my boss, we had a nice time and we moved on with our lives. Wrong. Oh, how I wish that were the case, but that is just totally, utterly and completely not. I dated Nick on and off for two years, all while working at the restaurant. Because he was such a player, there was a lot of jealousy surrounding our situation. I worked with and was friends with a lot of the other girls he had dated. There was certainly plenty of drama at work a lot of the time. Nick was a moody and dramatic person, so to see him all day during my eight-hour shifts, five days a week got to be difficult, especially if we were fighting. Also, he was a workaholic, so we found it hard to go out and do regular date-type things together, like go to the movies or concerts. Usually, our dates would consist of us meeting up after midnight to have drinks at a local bar close to his place.

At the beginning of our relationship, Nick asked me to keep the fact that we were dating a secret. He said it was to protect me from anything the other employees might think about me dating my boss. But mostly it was so there wouldn’t be any repercussions for him. At our restaurant, dating within the company was not strictly forbidden, but it was definitely frowned upon. Nick could have gotten in big trouble.

Of course, there were perks. Sometimes I got better sections or better shifts, I will admit that. And it was nice that I never got yelled at at work by Nick or any of the other managers. I got lots of free food and drinks, and there were secret rendezvous in the back hallways if I got bored at work. It all felt really exciting to me for awhile, and I felt somewhat rebellious. I think a lot of men and women have that fantasy about dating someone in a position of power. I did, and when the opportunity presented itself, I went with it. Do I regret my choice to date Nick? No. Do I think it was a mistake? Yes, it probably was.

So as I mentioned, I am not strictly opposed to the idea of one dating one’s superior, but I think the pros and cons should be weighed. There will most likely be jealousy and judgment associated with it. Or keeping the relationship a secret might become hard to handle. On the other hand, it can be exciting, and the perks are a plus. Every workplace is different, and has different rules as to what its employees should and should not do. Every situation is different, and please think long and hard before you dive in headfirst. Unless the boss in question is the perfect, charming Matt Damon look-alike I mentioned at the beginning of the article. In that case, don’t think twice. You have my permission.

About the author: Katy is an aspiring writer who just moved to LA from New York City. She used to work in the entertainment industry, but is now trying to figure out her life and what her next step may be! She loves movies, reading, writing and taco bell, and is enjoying getting to know LA.