Home Featured In Bed with a BOSS: How to date a WERKing Woman

In Bed with a BOSS: How to date a WERKing Woman



In the last few years, the number of female Entrepreneurs has grown tremendously. Women are no longer waiting in the wings for opportunity to find them, they’re out in the forefront of major corporations, building their own empires and taking the world by storm. So where does that leave their male counterparts? Sometimes, a little confused.

If women are no longer dating and marrying men for financial stability it forces men to “get in where they fit in.” Many times, business women find themselves too busy to make time for their personal lives, causing an even bigger rift with the men who may be interested in them.

Dating a WERKing woman may take a little more effort and some extra work, but it will certainly be worth it. What man doesn’t want a business-minded woman who he can trust to make the tough decisions and hold down her end of the empire? But, the question isn’t whether or not he wants to date her. It’s HOW does he date her? What does he need to do to make it on her calendar? How does he capture and keep her attention?

Here’s how:

Be assertive!

Don’t wait for her to make the first move. WERKing women spend endless hours leading meetings, making decisions and laying down the law but that doesn’t mean they want to be the boss 24/7. Business women appreciate men who know what they want and are willing to do what it takes to attain and sustain it.

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Be flexible!

When you’re an Entrepreneur or in a high level corporate position, THINGS CHANGE and sh*t happens. If you’re dating a WERKing woman, you have to be willing to roll with the punches. Your dinner plans may turn into a late night coffee chat. That vacation may end up being a work trip, when you’re the boss you don’t get a day off. So, when you’re dating the boss you have to be understanding. One of the biggest turn offs for a business-minded woman is the feeling that her man doesn’t respect her hustle.

Be dependable

In business, your word is everything. WERKing women expect their man to be true to their word just as they expect their business partners to uphold their end of the bargain. If she’s interested enough in you to put you on her calendar, DO NOT disappoint her.

Be supportive

Her business will more than likely become the family business, IF your relationship makes it to marriage. So, understand upfront that your support is expected. Make it your duty to go above and beyond to ensure her business is thriving and that she feels supported. Don’t wait for her to ask for your help with something because that may never happen. But that doesn’t mean she doesn’t need it or won’t appreciate it.

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Be confident

She knows her worth, so you better know yours! If you’re going to go after a BOSS, don’t approach her using those tired lines that work on basics. Put your best foot forward the first time because if you don’t, there may not be a next time. She won’t be easily impressed by things she can buy for herself, so you’ll need to be creative with your approach too. Think outside of the box and find a way to catch her attention and you just might capture her heart!


Business women believe in self-development and they have committed to being lifelong learners. In a world of flashy men, she wants the one who will engage in an intellectual dialogue, show her parts of the world she’s never seen, introduce her to new things and teach her something new.

Written by Koereyelle, Founder of TheSingleWivesClub.com and CEO of ReadyToWERK.com


  1. While I appreciate and applaud the spirit of this post, I have to disagree with the overall notion that its ONE gender’s responsibility to appeal to the other. I humbly, retort that compromise, adaptation, and assimilation must be encumbered by both parties. Part of the reason we live in a post-modern dating wasteland is because we continue to assume to assign roles to gender. We continue to straddle the fence between progress and tradition. “Werking” women should understand that they have to be just as adaptable and flexible as the man who has interest. Just because a gender is in a particular social status does not give them an out in making concessions to make a potential relationship work. I see and hear of too many people who project that they have it ‘all together’ and that others must conform to their value system. I feel people with this mentality are not fit for relationships. Standards are great, but we must not be so rigid that we don’t leave room for nature to occur naturally.

    1. I agree 110%. I think a big problem today is women have started to bring their life on social media to the real world and have no flexibility of give-and-take. They have gotten so used to just logging in an app and having guys thirst for them and have options at their finger-tips and then they feel the need to do no work whatsoever. They will sit back and wait for the guy to do everything, no foot forward on their part and continue to do them. “Werking” woman have just as much capability to make the moves a “Werking” man can. She can initiate a date, she can invite to dinner, she can do everything this article said as well.

      Standards are great like you said, but the word RECIPROCATION is not understood today. No one wants to give, just get. Get the initiated conversation, get the set-up for the first date, get the gifts, get the fun from the person taking them on the date.

      1. Yes it’s a conundrum that many modern women find themselves in, especially the ones who subjectively wave the flag of feminism. Many times at the expense of their own ideology. You can’t want to be considered and respected as an equal, and then retreat to traditional social values when it benefits you, that goes for both genders. Yet, we continue to hold one another to sometimes unrealistic expectations, under the guise of already “having our ish together.” Natural interaction no longer takes place because we play checkers, chess, poker, etc in the dating world. We treat interpersonal relations like a true capitalist: minimum risk, minimum benefits offered, and expect maximum profit. We have to be mindful and realize that the quest for meaningful relations is like a boxing match, many times you have to take a punch in order to land a good one, anyone can throw the first punch, and getting down is fine as long as you keep getting up.

      2. “They have gotten so used to just logging in an app and having guys thirst for them and have options at their finger-tips and then they feel the need to do no work whatsoever ”
        I hear a lot of women complain about the numerous attempts to get their attention from thirsty dudes. The caveat being that those dudes don’t interest those women. Similar to how you will have a thirsty chick that you are not even remotely interested in trying to sip ya koolaide. So its an interesting conundrum, indeed.
        Never anything wrong with common courtesy, manners and chivalry – a little can go a long way. But people seem to want to pick and choose, and they have that right, what old traditions they want to hold on to and which ones they want to dropkick, and when you exercise that right, just like anything else, there are consequences.
        Aaaaaahhhh….but I have turned on to a sidestreet and gotten somewhat OFF topic. My apologies.
        BACK TO THE SUBJECT……………….GO! lol

      3. No offense, but only you are responsible for the women you choose. There isn’t a topic that is completely one sided. Just as you disagreed with the direction of the post you went to an extreme side. Do men not do the same things you mentioned? Your temperament and action is not exclusively across the board the same way every man will react.

        1. You’re right I probably should have wrote it with less tones of generalization, but yes men do the same thing, but I don’t think they do in the beginning because we are expected to initiate. Men are the ones expected to ask for the date, get the number, etc. so it’s more likely for women who are the pursued side to just sit and do nothing and wait. Now, once the chase is done, yea the guy may get lazy and the girl when she already has feelings turns into the pursuer putting effort to get things back to the way they were in the beginning when the man was loving, etc.

        2. I guess we’ve had encounters with very different experiences. I’ve meet enough people to understand we’re all individuals and should be treated as such. Chase should not be be a literal chase of running behind someone with a tone of begging. Asking for a date only initiates the experience. I have never understood pursuing a person who clearly is uninterested. You shouldn’t waste your time, nor continuously create the same experience. Clearly these women are not for you.

        3. Pursuing dates from someone who is clearly uninterested is different. I’m talking, even when both parties are interested, it is the man that is expected to ask. Women rarely will be the ones to approach, get the guys number, and “would you want to go for lunch sometime”, my point is you can have someone be interested but it isn’t until after the first date they say “You know, he’s not for me” and the girl proably made no effort to keep it going

        4. I understand, but you stated chase, and to me that’s more than simply asking a person out. I just think its more complex than that. Women aren’t all that shy from my vantage point; they don’t tend to just let the man lead in all aspects of the chase without any input. If this happens often then that within itself is odd to me. Sane men don’t typically chase without that input or reciprocal flirt. If it were me I would have to reflect to determine what I was doing wrong. It’s not always the other person.

          Personally I don’t date without talking on the phone to see if we vibe well. If we don’t then there’s no date. Some things can’t be forced.

  2. I totally agree with the perspective, and that is all it merely is. From where I am standing, I don’t feel there was an indirect stab at men to cater to women or sacrifice their own moral standing solely for “werking” women. I see it as one side of a bigger picture and posts similarly to this allows us to slowly put the puzzle together or at best see things from a perspective they may have not considered.

    The reality is most individuals SOLELY consider and seek to fulfill their own needs/desires, above all. I am that rare individual who truly considers both sides and self reflects constantly. I am a natural leader but I don’t try to control or “man-handle” anyone or any situation. Leading also permits concession and compromise, and if two individuals are on the same path then they know enough to make it work and choose the battles.

    I constantly run into men who try to define who I am for me, without getting to know me. Needless to say it’s a big turn off, but I simply accept those men are not for me. I shake it off and move on. A working woman is not a threat and shouldn’t be considered for anything other than compatibility. These are all simple tools to assist with aiding balance in a relationship.

  3. Now this is a list I can rock with 100%. Kudo’s, applause, and a standing ovation to whomever created this list. 🙂
    All very true. And these don’t just apply to “boss” women in Corporate America; but also women who have a “boss” mentality, and can run a household, have their own business, and know their worth and value. Being a “boss” imo is not just about your career/business, but it’s a state of mind that becomes a part of every aspect of your life.
    My mom, grandmom, aunts and many women in my family don’t all have their own business and don’t all work in corporate America; but please believe they all have a “boss” state of mind. They live it and it shows.


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