Dating Your Boss
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.
Popularity: 11% [?]
September 14th, 2007 at 1:52 pm
That is the trouble with office romances - that when things go wrong, it causes a lot of trouble. Nick seems to be a serial dater - very bad!
September 14th, 2007 at 6:27 pm
OK, one of two things needs to happen!
1) You quit!
2) He quits!
Office romances are so taboo! Just don’t do them. There are millions of men out there, can’t you find one that does not work with you–and even more important, that is not your boss.
Read Mama Peavy says, “Women, It’s OK to Marry an Ugly Man” by Mary R. Butler. It will give you a new perspective on dating.
September 15th, 2007 at 1:20 am
thank for sharing this. I like it.
September 15th, 2007 at 10:32 am
A good experience. When the romance ends, there can be difficulties for one or both sides.
September 16th, 2007 at 3:51 am
I dated my boss at a restaurant. Then I married him. We really didn’t have much in common but we hung in there for seven years. There is definitely a draw to that position of power.
I find that it’s difficult enough maintaining a love relationship without adding the whole coworker weirdness to it.
But that’s just me. After all, I did it. Who am I to judge?
September 16th, 2007 at 4:33 am
I know I won’t be doing that for a long while, but now-a-days how else do you meet people if you’re not in school anymore.
It’s a tough choice that requires a lot of thought and weighing out the pros and cons.
September 16th, 2007 at 6:09 am
Thanks for sharing your story. This really opened up my eyes on the pros and cons of dating in the same working environment especially if your dating your boss!
September 16th, 2007 at 4:42 pm
NO! WAIT!
Just in case I finally get famous and have an office and a big mohagoney desk (the great view will have to be from the ground floor, though. No high rises for me)
But, just when I get famous and all that other, and I’m waiting around fer some pretty thing t’claw her way upward bound on my naked body…
well, YEAH!
C’MON! PLEASE!!!!!
dang. If it ever happens will be the day all women make a pact t’never sleep (?) with their bosses ever again ON THE WHOLE PLANET!
September 17th, 2007 at 3:24 pm
I’ve married my female boss :), happens
September 17th, 2007 at 7:57 pm
Interestingly enough, neither Nick nor I were forced to quit the restaurant because we both ended up moving away from NYC at around the same time. But there were DEFINITELY times when I considered just walking away and quitting. It was either that or get him in big trouble and I really didn’t want to do that, even tho I could have
Some of you guys are right though, one never really wants it to get to that point where you are forced to leave your source of employment! That was something I should have considered more seriously before I dove in headfirst!
Also, interesting to read that a few of you dated and then MARRIED your bosses!-sounds like it probably happens a lot more than even I thought.
As for (boneman) haha…don’t lose hope!! I wish you a torrid office affair/romance with your hot, cougar boss in your highrise office bldg….on the ground floor.
September 17th, 2007 at 9:46 pm
Wow! I loved this article. After reading the 2 intro paragraphs, I was hooked. I’ve never dated my boss, but I have dated a co-worker. It can be tricky, especially if your other co-workers love to gossip (who doesn’t!)
My relationship with my co-worker ended, and he left the company… it’s so annoying because now everyone stops by to ask me how he’s doing. It’s a constant reminder…
I would love to hear more from Katy! Does she have any other articles?
September 18th, 2007 at 9:10 am
This was a great article. Thank you for posting. Although I have never dated a boss or co-worker, I have known a couple of close friends who have, neither of which ended well. As the author Katy said, the perks can be great, but ultimately it becomes too stessful. However, there are always excecptions to the rule.
Katy, I want more! I can’t wait for your next article, especially if you post more pictures of yourself
September 18th, 2007 at 2:14 pm
When I was in college (the first time) I was living with my girlfriend and we ended up getting hired at the same place. Big mistake. Spending all day with her at work and then being with her all the time at home was brutal. It wasn’t that I didn’t enjoy her company, but you can only take so much of one person before they start to drive you batty.
Aside from that, I’ve never been involved with anything more than rampant, shameless flirting with a co-worker and think the old adage of not dipping your pen in the company ink is generally a pretty good way to go.
September 18th, 2007 at 2:33 pm
I am totally against dating a co-worker or boss. I have been in both situations and have been the boss too, lol. God, it can get ugly when it ends and it is so uncomfortable. Personally for me, I was able to move on and continue as a professional however the other party was not. It is something I would never do again. Love your post!
September 19th, 2007 at 2:59 pm
Good post. I was a little afraid that this post will be a post on how to use “dating superior” to get higher positions.
I agree to what you mention in this post. It’s a great post because it mention the situation might get into when a woman try to date her boss. Your experience is worth sharing and I think helped some people who are still considering about this.
Great sharing. =)
September 19th, 2007 at 8:36 pm
[…] Read All >> This entry was written by and posted on September 13, 2007 at 9:28 pm and filed under Dating and Relationships Opinions, Dating Tips. Bookmark the permalink. Follow any comments here with the RSS feed for this post. Post a comment or leave a trackback: Trackback URL. « When All Trust Is Gone, And Gone For Good Hot Muslim Guys » […]
September 20th, 2007 at 1:22 am
Great article! Is there more to come? I loved it! :0)
September 20th, 2007 at 1:24 am
Oh goodness. If you only knew. One of my peers is dating our boss and although they are trying to keep it a secret, it is obvious to everyone. What makes it even more difficult is that he (my peer) is one of the worst teachers in my building and no one can say or do anything because he is seeing my principal. It’s actually making me want to leave my job. UG. However, I enjoyed the great article and awesome writing. SMILES!
September 20th, 2007 at 1:28 am
I once dated a superior of mine…………… and then he went to China. Men suck. Love you!!
September 20th, 2007 at 1:32 am
Katy, your situation sounds both fun and stressful. Thanks for sharing…
September 21st, 2007 at 9:45 am
Good stuff! Currently I am dating my boss, I met him online through wealthyromance.com. He asked me to work for him… so I went to his company. Now we are dating…GINGLE. he is a nice man. I think I will fall in love with him soon.
September 21st, 2007 at 6:05 pm
Hmmm. .I seem to remember benefitting from your situation when I was in NYC to visit you as well, never turn down a free drink :). Great job on the article!
September 22nd, 2007 at 12:50 am
First off, awesome story. Really well written, and really hot author. While reading the comments though I noticed a lot of people tried to relate to this story by talking about their “office romances.” I think there’s a fundamental difference between your typical office romance and a restaurant romance. The difference being that everyone hooks up with everyone else in a restaurant.
An office romance is tricky because it seems like the people involved usually have spouses and it’s relatively secret. A restaurant affair everyone finds out about almost immediately. In an office you have to be careful with touchy behavior. In a restaurant sexual harrassment is the rule.
At the end of the day working in an office and working in a restaurant both typically suck and you shouldn’t hook up with anyone from either place. However, if the opportunity to hook up at the actual workplace comes up, like on location- then you’ve got to go for it because that’s just hot.
September 22nd, 2007 at 4:17 pm
Definitely something not to jump into w/o thinking twice about it. Usually doesn’t work out well, however, can be very exciting and certainly a learning experience in both relationship and work arenas.
BT,DT.
September 23rd, 2007 at 4:58 am
The workplace romances are awkward all around…bystanders are often conflicted by loyalties to both (all) parties involved…his loss, you’re really hot!
Great article, give us more!
September 24th, 2007 at 12:07 am
I have had and survived office romances. It’s definitely a tricky business though! The first time I dated a co-worker, we kept it secret and played it very cool at work. I eventually changed jobs for career advancement reasons, and then it was ok. However, we ended the relationship, and then a few weeks later, he comes and joins my new company! Now THAT was awkward for me. I told my other co-workers about the situation and they were very supportive of me. Fortunately, both my ex and I were mature enough to talk things through and we became friends afterwards and managed to work together very well. However, I did get jealous once he started dating another co-worker.
The second time I dated a co-worker, we fell in love and ended up getting married! So there can be happy endings, so long as the reasons for dating one another are for real, and not just for the excitement of doing something that is considered “taboo”. Now we both work at completely different places, which I think in the long run is much healthier to have some distance and independent lives away from home.
I’ve never dated a boss, though. I think that is the most dangerous type of relationship in a workplace. It’s just bound to explode in a nasty way with either you or your boss, or both, having to leave the company. I admit I’ve had fantasies about having sex with the boss. It must be some Freudian power-trip thing going on. Being accepted by a father-type figure and meeting his/her approval. Great article! Gets a lot of discussion going!
September 26th, 2007 at 9:04 pm
Thanks for your insight! I dated one of my superiors and you are right, it can be very fun at times but it can also get very complicated.
October 3rd, 2007 at 4:33 am
It seems like unnecessary drama to me.
November 21st, 2007 at 6:19 am
Katy - you are one hot chick… and if you wear outfits like the one in your picture all your bosses will want to date you
Love your writing… is there more to come?
December 15th, 2007 at 6:40 am
I REALLY LIKE THIS ARTICAL I FOUND IT TO BE KIND OF WHAT I AM GOING THROUGH! BUT ALL I HAVE TO SAY IS KATY IF I WAS AS HOTT AS YOU ARE THEN IF I WAS YOUR BOSS I WOULD HAVE DEFF. ASKED YOU OUT 2 FORSURE!!
May 21st, 2008 at 8:59 pm
I prefer not to have a date with my boss because it could bring a lot of trouble…
July 24th, 2008 at 8:03 pm
I found this article to make me want to ask my boss out - Atleast something interesting will happen.