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May 21, 2013 / admin

Pining From Afar: What to do When you’re In Love with your Boss?

I love the male participation we’ve been getting on this blog as of late. Don’t stop telling your side of the story, gentlemen! After all there are two parts this equation and the better we can understand and communicate with each other, the less we will view White Men or Black Women as strange aliens from another planet.

This question below was posted by Barry. Since you all gave such wonderful advice on the post “Where are the openminded Black Women”, perhaps you can also steer our lovestruck Barry in the right direction as well.

i dont really have any advice, but i do have my own personal delema … LOL the black lady that i am interested in is actually my Superior, im in the Military and she being an Officer brings its own callenges that are very unique … i have to deal with the whole issue of “Military Protocol”, and i cannot just walk up to her and ask her out … “or could i” … ?i have known her for 3 years now and she always catches my eye whenever we are interacting “in a working environment” funny thing, i”ve actually given her a ride on my Motorcycle, we were doing a fitness test and afterwards she seemed very tired and i told her “hop on” without a second thought she jumped on my Motorcycle and it was just the most amazing feeling to feel her beautiful arms around me …i do see her often at the Military Gym and always make an effort to chat to her. After 3 years she must suspect that i am obviouslly “in love” with her. but i dare not ask her out, after all she is an Officer and my Superior … what to do … ?!

My advice:

I have never dated or pined after a work superior or had a work relationship, but I do feel your pain. I mean, you want to keep your job so you follow the rules of that job. There are those who say NEVER $#*t where you eat. In other words, if that relationship goes south you are then faced with the awkward position of seeing that person each and every day. If you two are grown ups about it then it’s not so bad, but when one person has a propensity to be a drama king/queen then it really sucks.

You could try to keep things quiet, but ultimately most couples aren’t good at hiding the fact that they’re sleeping together. Either they try too hard to avoid each other (raising eyebrows) or they start finding every little excuse to spend all their time together (raising eyebrows). There’s also the gossip and speculating of the co-workers who feed off any little information that even remotely resembles a scandal.

Anyway, my point is you wouldn’t want to find yourself writing cover letters just because of a few weeks/months of pleasure, or do you? I think when it comes to dating a boss, the boss always needs to be the one to make the first move just to play it safe. In your case, you might be waiting forever since most women just aren’t trying to make the first move (or she could be thinking she’s giving you the signals and you just aren’t getting them). I’m sure there have been instances that have worked out when the opposite has occurred though.

I think in your situation it might be best to just try to befriend her, without becoming “the bff”. In other words, keep the sexual tension and don’t become the guy she talks to about ‘girl problems’, like other guys. Be subtle with your flirting and still keep an open mind to other women. Undoubtedly, women always become more interested when you see that you have options.

Good luck!

Ladies & GENTS – sound off below!



Leave a Comment
  1. labellenegresse1 / May 23 2013 7:48 pm

    I stick to the old rule of never pooping where you eat.

  2. Insomniac / May 24 2013 2:55 pm

    You could write her a note briefly saying how you feel, and then include how she could reply back, if interested. Or if you don’t want any paper trail, you should just tell her face-to-face.

  3. Average Guy / May 27 2013 1:47 am

    This is tough, but being a veteran, I can tell you that they take the whole “fraternization” thing very seriously! One or both of you could have your careers ended, she being an officer, she is especially in jeopardy. The old adage of crapping where you eat definitely applies. I do not know if I could stay away if I was in your shoes, but if you care about her, you certainly don’t want to risk her career.

  4. Nina / May 27 2013 9:22 am

    I would say go for it, let her know you are interested in her and go from there. What is the worst that can happen, hearing no is not new to anyone, but knowing were you stand can go a long way. Who knows she may feel the same way, but at least plant the seed before someone else comes along and acts on their interest, then you will be mad for not even trying.

  5. Kiwiwriter / Jun 9 2013 5:28 pm

    If you are enlisted, you could get in extremely serious trouble for getting involved with an officer, particularly YOUR officer. The military gets nervous about junior enlisted dealing senior enlisted and positively apoplectic about enlisted dating officers…I know this as a veteran.

    If you were to ask her out, either way, it could wreck your career. If she says “no,” she can turn around and write you up. If she says “yes,” and you get seen as a couple, her bosses — or your senior enlisted bosses — are likely to write you up, even if they’re your pals, because you two being together has a serious implication for the chain of command and maintaining discipline.

    The scenarios that can result are scary: you and her start dating, she arranges your work schedule so that you can see more of each other, the other guys get irritated at having to police up the filter tips while you two go to the beach…or while you two are lying intertwined in bliss, you start talking honestly, and you tell her what you really think of your buddies, and that stuff winds up on their evals. Or she starts telling you that your mutual boss is a drunk and a jerk…and the various parties find out.

    Next comes the call to the Inspector General, the Command Master Sergeant, or the CO, and the two of you are popping tall in Class A uniforms before the Man. Not good.

    I think you’re beat, unless one of you is prepared to leave the military. Then it ceases to be a problem.

    The problem is not your ethnicities…the military is a very different and socially isolated world from the civilian United States. It is an extremely different lifestyle, with its own complex rules and customs, and the system is not designed to promote personal happiness…nor does it protect its members…it protects itself, and the country, in that order.

    Sorry. I wish I could give you happier advice.

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