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Dating in the Workplace



I consider myself still very new to the corporate world. In May, I will be out of college for two years so there is still much for me to see in the “real world.” In my short time in the office space, there was one experience that to this day cracks me up. Allow me to paint the picture for you all.

It’s October 2011 and I’m at a state training in Harlem for my new job. At this point I had been working for a couple of weeks but new people were still being hired. I walk into training and what do ya’ know there are two new, very pleasant looking women.

As a guy in the workplace, you can’t front. It’s real nice when some new women end up working with you. It’s just nice to see nice women; it helps the day go by. Now it just so happens that no one is sitting with these young ladies. With them being new, I decided I would sit with them and introduce myself. What ensued thereafter was nothing short of what I find hilarious. You see, as the day went on the other guys in the office were doing their damndest to flirt with these women. The problem with their approach was that it was sophomoric. They made a lot of silly comments towards them, got their names wrong, etc. Not the best way to leave a first impression. Fast forward to today. I’m still on great terms with both ladies and those guys never got what they were looking for.

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Today’s post is about workplace romance. Some people are completely against it and I think that’s with good reason. I have no empirical evidence to back this up but as a man, I would think more men are comfortable with this than not. The example I gave you earlier was essentially how not to go about approaching a woman in the workplace. I believe discretion is everything in most areas of life.

The workplace is really no different from school. You’d be surprised the kinds of nonsense that goes on in the office. Everyone doesn’t have the highest level of maturity. That’s why you have to also beware of people who simply like to gossip. The advances you decide to make with someone on the job should be extremely subtle. That woman will talk to her girl on the job about it, and you need to be sure all your moves are flattering.

You have to move like someone is always watching, so that means you can’t be too obvious with your approaches. Fellas, you also have to take the time to feel a woman out. It’s extremely important you figure out the type of woman you’re pursuing because it can truly blow up in your face. For example, learn about how far you can take a joke with a woman or even flirt, preferably beforehand. A guy on my job was fired for sending a text of his beef to a woman he liked on the job. Apparently, she didn’t want to see it and reported him.

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I’m not saying do not text a woman what you want to text her, that’s all on you. What you must bear in mind is that he paid the ultimate price because he didn’t feel that girl out enough. Men, we have to be very cognizant of our boundaries, especially in the workplace.

A woman has to be receptive for you to be able to engage with her romantically in the workplace. You have to be able to trust that she won’t spread any foul rumors about you. In the event of a breakup, you also have to make sure that you end things amicably. The biggest hang-up most women have with these type of relationships is that they feel it’ll make things awkward. It’s my mantra that things become awkward only if you make it awkward. For two people to participate in a casual romantic relationship or something more, both parties have to be adults about it. There’s no doubt that romance in the workplace can be exciting. I’m all for the excitement; live this life and create memories. My only advice is do not go into these situations without weighing the pros and cons. In other words, keep your beef to yourself untill you know the coast is clear.

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These are my words and I make no apologies.

– DamnPops

“I’m not a biter, I’m a writer for myself and others.” Brooklyn born dude trying to figure out this life just like you. Come on this journey with me.

Follow me on Twitter: @DamnPOPS

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  1. Good article.

    I think its cool to have a rule somewhere along the lines of "no dating in the workplace" until there's somebody worth breaking that rule over. The truth is that for most of us, we spend at least 1/3 of our day in this environment. This is generally where we make most of our new connections and have our general conversations. I think its only natural to develop feelings for somebody you spend that much time with. But if you act on those feelings each time, you wind up with the awkward environment of everybody of the opposite sex in the office knowing your business and suddenly things start being said about you that aren't so nice. But at the same time, I know several couples who met on the job, dated, and wound up getting married.

    Some things I'd consider
    – How long do you(they) plan on keeping this job and how certain are you about that? If I knew I had plans to leave the firm and start my own company within 2 years then I might be more willing to mingle.
    – What are your positions? Is one of you in senior management and the other a part time worker? If so then the office romance may not be as easy to navigate, particularly in the case of a breakup.
    – What are your locations? Its one thing to say that we work together, but are you like Jim and Pam from the Office where you're literally sitting side by side all day, or is it more of a thing where you have the same logo behind your name, but one of you works in DC and the other in Rockville?
    My recent post Sudoku Program Updates

  2. I’ve learned my lesson dating in the workplace that now when a coworker been throwing me lobs I act like I don’t see it…..Greg Monroe. The perk to a girlfriend is getting away from work, the perk to work is getting away from your girlfriend, you mix the two, you can’t win *Adrian voice*. So at best I flirt and I leave it at innuendoes and mystique.

  3. It's hard not to date someone in your workplace when you work in a large corporation. You are always see new eye candy and you are more often forced to be non sexual in your advances which allows the man to get to know you better and vice versa. Which is opposite in public because a lot of guys do not know how to approach a woman, whereas in a work environment you have to have that delicate balance for the fear of HR. Me, personally, i prefer to mess with someone who is not in my department so that I do not have to see him a lot or see him flirt which may incite jealousy. All in all, if done correctly you could come into a great friend or a great relationship!
    My recent post That man walked off with my stuff…..

    1. Exactly. People are always talking at work so its the perfect opportunity to meet somebody and have it develop, especially over time.

      The problem comes in when a person (normally this is a guy) mistakes a co-worker's behavior as being flirty and thinks "oh, she must be into me" and then suddenly makes an overaggressive move in the workplace that I'd hesitate to do in the nightclub. That's when things wind up at HR.
      My recent post Sudoku Program Updates

  4. Great Post!!! i can relate to this! I work at a call center and i made a pass at this guy about a month ago. started out as both of us sitting beside one another, he started talking and Bam, we had great conversations. he didnt ask me for my number so being bold at the time which is something i raely do, i wrote my number and name down on peice of paper put in on his windsheild and then only for him to call me after 1:00am saying he dont want to break up a happy home, his ass had a girlfriend. DAMN! some of that is my fault but i had my eye on shorty since he came through the call center. but even after all tht we have conversations but his ass is kinda moody at times like a Bisssshhhh! But i say all of this i take this as a lesson learned. i will never not date or try to date in the work place. Flirting, i do tht all day. also i will never try to holla at a guy again because i lack game, besides men do this, i will stay single 4 eva if i gotta spit game! lol

  5. It certainly all boils down to whatever floats your boat. As a woman who's worked for large companies since being a teenager (intern) and now as a young adult, I've seen plenty and still do. Personally, I choose to not cross the line with my single male co-workers. I just have a bottom line in you "don't keep your honey where you make your money." You're risking a lot, including your job AND your reputation. As a woman, I know that we are more cognizant of our reputation especially as it relates to men, there is something to be said about a woman who has now been dubbed the office whore – yeah, it can get that deep. However, there is a part of me that believes in "fate" or things just organically happening….but as far as using the work place as your personal social scene to feed your emotional and/or sexual desires is a no-no.
    My recent post x "Could You Be Mine?" Part II x

  6. Hmm, I think workplace romances are 1 of those things that you can view as if you're in college. For example if you to go to a school like The U or UM, it's not likely that you'll have problems dating someone on campus. Those schools are so large and you can easily float through 2-3 co-eds at the same time w/out them knowing about each other and w/out too many people knowing your business. On the other hand, if you go somewhere smaller or even an HBCU, everybody kinda knows everybody. It's very insulated so observers will be able to chronicle your dating situation; from the approach to the break up.

    I say that to say, dating is fine when you work at a large company. It's even better when you maybe don't work in the same dept. But if your company employs less than like 50 people, you might just wanna chill.
    My recent post The Lent countdown and fighting temptation

  7. Good topic for discussion!

    Eeeek! Can make for a sticky situation if it doesn't work out well.

    After I college, I took a job back at home in California and became quick friends with one of my coworkers (chick a year older than me). Sometime later, I confided in her that I had a crush on someone we worked with which she described as her "best friend". She told him (she said she wouldn't….oh to be young and naive), but it worked in my favor as we began dating shortly after, unbeknownst to her. Eventually she found out and began calling my cell repeatedly leaving all type of crazy voicemails, sending students (we worked in a HS) to deliver hand written messages to me…. all out childish/crazy behavior. I later find out from "best friend" that she was also interested in him, but he wasn't feeling her like that. Luckily for me, I had plans to move to the East Coast at the end of the school year leaving them to sort out the details of their "friendship".

    I was fortunate to learn early on in my career not to sleep where you eat. The work place might be "like school", but now that I'm older/wiser, I try my best not to treat it as such. I think of it now as feeding the fantasy of the "mysterious" librarian. ; )

    1. Girl, that story was WAY TOO familiar, lol.

      …made me feel better to know that random ridiculousness happens to other folks as well, lol.

    1. She must work for the federal govn't, LOL…cause we wear sandals 'round here!

      Is closed-toe shoes a corporate rule?

        1. o/

          We're fairly casual here. I have on open toe shoes right now and unless it's freezing or there's snow on the ground, I wear them most days.

          But I'm also in the MidWest…in a psych hospital…in the office…not a corporation.

  8. I did that same mess to when I was younger, too. Let's just say that I learned my lesson to not play where I eat the hard way.

  9. Great Topic! My take on this is exactly as you said. But to go a little further, one thing I would like to men to be mindful of is that you make us uncomfortable with these approaches. Just because we're nice to look at doesn't mean we should be pursued. Two reasons: the first is that we are on to your game. if you're thirsty to be go after us, we're sure you have already done it to the other women working there and will do it to those to come. Second, we are there to WORK! We need money and the opportunity to focus and build our career without worrying about different ways to tell you to, "get the hell out of our faces." this is why I also HATE the gym. I am here to work out. Please allow us to live. Thank you for being appreciative of our beauty but be easy. PS: Your approach to the new women at your job was excellent. Make us feel welcomed….not eerily stalked.

  10. hey, whatever works for you. Been there, DONE THAT…got the tshirt to prove it. LOL. As someone said, knowing WHEN to break that rule or knowing when someone is what I call A RULEBREAKER is key. I've seen some office romances turn into marriages, I've also seen some Drama in the office as well, so it just all depends. Personally, I've done that enough on my old job and once on my current job, so I'm sticking to the rule of NO OFFICE ROMANCES FOR JT…..then again, you just never know.

  11. I know it's bad practice, but I'm guilty of sh!tting where I eat. Happened 4 times, only blew up in my face one time and even we're cool now. #ShrugLife

    As an adult, it's hard to meet people. Sometimes it's just "easy" and "comfortable" which we all know are not the ways into healthy relationships, but ish happens.

    As a counterpoint, several office romances at my job have turned to marriages – not that that makes it a good GD idea, just saying.

  12. I was actually going to pen a post on this very topic.
    In any event, workplace romances are the shiznit if done properly, and if the right mate is chosen. Otherwise, serious problems can arise. Maturity is the most vital element for this experience to be throughly enjoyable for both parties. Without it, drama, drama, drama.
    You pretty much covered many of the considerations that should be explored before embarking upon such a risky, yet enjoyable romantic endeavor.

    Good post.

    Mr. SoBo

    My recent post 10 Things Every Mother Should Teach Their Daughters

  13. I'm from the school of thought that you don't get your meat from the same place that you get your bread, if you follow what I'm saying. It could work, but it's not for me. After the honeymoon period ends people tend to act very differently, not a risk that I'm willing to take at work. Also, as a black woman in public accounting, I have to be very careful about separating my personal life from my private affairs. As it is I'm "the black girl" in my firm. I don't want to also be "the black girl who used to bang (insert name)". Not for me.

  14. I had my "work husband" WH. we kept it on the down low. it was one of the great four years at the agency. We worked in different departments. He pursued the hell out of me and when i finally decided to walk the walk it was quite fulfilling. We talked on the phone didn't do much emailing on the work computer due to it being monitored by IT. the emotional and physical support was fantastic. office romances can be heaven or hell. you really need to choose a female who can keep her mouth shut and a man that steady.


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