How to date successfully as a high achieving woman

A narrative I hear time and time again from high-achieving female clients who sign up as a member with Cocktails & Conversation is that they are constantly meeting men who are intimidated by powerful, successful women

A narrative I often from high-achieving female clients who sign up as a member with Cocktails & Conversation is that they are constantly meeting men who are intimidated by powerful, successful women.  Although I don’t doubt that these women’s experiences in dating have shaped this belief, I have never had a male client tell me he is looking for a woman who isn’t too smart or doesn’t earn too much money.  This contradiction got me very interested in the real root of the problem.  I wanted to find ways I could help my female clients to date successfully as a high-achieving woman and attract the type of relationship they are looking for.

Firstly all the women I spoke to say they have no problem attracting men for dates, they are always in great shape, well-groomed and with above-average appearance. They find there IS definitely an issue with sourcing enough suitable men who are potential partner material. However, when they do find a man who ticks all their boxes, he generally loses interest without a clear reason why. This leaves her with an understandable feeling of pessimism and frustration. Feeling like there are no good men out there left who can handle a strong and driven woman.

date successfully as a high achieving woman


I asked the men how they felt about successful women


I could have reasoned they “whys” from sunrise to sunset.  Each client has her own reason why she believes men are failing her in relationships. This would always be a theoretical explanation because they, like I, as a woman can’t speak for the men they’re dating. Although I have my theories, I can’t fully answer why the men they’ve been meeting won’t commit.  Or why they seem to lose interest and drift away without explanation (or at least one that makes sense).

So I turned to the men to fill me in, and I’m going to paraphrase the results of many conversations. Conversations with single men and with relationship experts and therapists. And give the most simple answer I can and a 5 step strategy that I have used with my members that has actively helped successful and high achieving women solve this problem and find happy and fulfilling relationships.


And the answer was?


First of all, let’s look at the traits that are most common in very successful women, that develop success in a high-powered career. You are focused, goal-oriented, assertive, logical, analytical and a strong negotiator. You have developed these qualities and they have served you well in order for you to earn six or seven figures. But they are not serving you well in your relationships because these qualities also come with a large amount of what is referred to as “masculine” energy.

Masculine energy in itself is not a problem unless it is out of sync with your “feminine” energy. These are qualities like being open, yielding, receptive, flowing, soft, nurturing, warm, and creative. In short…

“Masculine energy is about doing, while feminine energy is more about being.”

This is the fundamental duality of masculine and feminine energy that ignites and maintains the arc of romantic attraction between a woman and a man. Think of it as a dance, if you’re both trying to step off the same foot, you’re going to keep stepping on each other’s toes.



If you are finding yourself off balance with this energy’s here are 5 strategies to bring them back into alignment and date successfully as a high-achieving woman…


Communication is Key


  1. Build Pre-Date Anticipation

I often hear successful women planning before work coffee dates to check the gentleman out and see if there’s a spark. They invest no time in qualifying him properly or building a relationship through communication before the date.  This often leads to the woman being ghosted because there is not enough interest or anticipation pre-date.

Communication is a key feminine trait so insist on it, get to know him and let him know a little about you before you meet for your first date. If either of you doesn’t have time for a call or facetime or two then you won’t have time for a relationship either. This also helps weed out married or unavailable men who can’t easily chat on the phone in the evenings.

date successfully as a high achieving woman


  1. Talk with grace and charm

Femininity is soft and graceful. Often when I start consulting with my female clients I notice they cut directly to the chase and bypass small talk and niceties. It’s a sort of time is money attitude but this isn’t the energy we need in a relationship.  Slow down, let’s get to know each other before we talk business.

Try not to lead and hijack the conversation by asking lots of direct questions as if it’s an interview or even worse, an interrogation.  Men don’t respond well to this type of communication when they’re out of the office. Being direct, blunt and putting a lot of energy in showcasing your intelligence, often comes off as being difficult, rigid and brash. This can be step one in intimidating or putting off a man.



How to change this: Do not date when you’re in work mode, if you are dating after work come home, have a bath, listen to your favourite relaxing music, change into something softer and let your warm and playful side out. Avoid quick coffee dates or any type of date that could be a work meeting.


Learn to yield but not fold to date successfully as a high achieving woman 


  1. You are not his therapist!

Successful women are often fixers, this is why they can often end up attracting toxic men or men who need a lot of fixing! Have you ever found yourself analysing his state of mind? Or offering solutions to his life problems like work, finances or living situation? Then you are a fixer and this is masculine energy. You want him to be the best version of himself and ultimately the best man for you. However, it’s a mistake for strong women to openly psychoanalyze their partner, or respond to his weakness or difficulties by trying to coach him.


This is the exact opposite of what a quality man wants from his partner.  Instead of feeling supported and encouraged, he will feel emasculated, judged and repelled.

Men want from their lovers what they usually can’t get from co-workers and friends: warmth, affection and nurture. Sometimes of course feedback and advice are welcomed, but on the whole, when you’re getting to know each other it’s best to listen without judgment or advice.


How to change this: Relationships should be a place of warmth and support, not a place to get processed and challenged. Instead of pouncing on flaws and issues, tell him you support him and trust him to solve problems and challenges as they arise.


  1. Let him lead

Unless you want to be the alpha in your relationship (and it’s fine if you do), you will have to learn how to let go of the reins and let him lead.  Most women I work with want the man to be the dominant one in the relationship, but struggle to give him the reins.  You are so used to being in charge in your daily life that handing over responsibility can give your anxiety.  Remember you are going to be leaning into your feminine, which is more being and less doing.  You must let him do, as in plan dates, even if it’s not his strong point, cook you a meal or rub your shoulders sometimes.

date successfully as a high achieving woman


Offer him the space to lead the relationship without pressure or demands to do it your way.  If he doesn’t make plans when you would like to see him, book yourself a spa day or make exciting plans with friends. Don’t push or nudge him to do so. With this strategy you will demonstrate patience and gentle strength. He will learn you value your free time and prioritise yourself.  When he leads correctly he gets the reward of being with you. If he doesn’t put in the effort of leading and drifts away, he probably isn’t the man for you.



  1. Explore your femininity

In general, the message our society delivers is that that femininity equals weakness and a disadvantage. Hence we feel the need to actively prove to the world and to men that we are strong and equal. We can carry our own bags, open our own doors and pay for our own meals, which of course we can but… Isn’t it better when he does these masculine things for us?  I don’t believe we NEED to prove anything to anyone. What we need to be proud of is our divine feminine radiance and embrace our strengths as equals but different.


One thing that will help you date successfully as a high achieving woman is to step into your feminine energy. Learning how to express your sexuality and know what turns you on. Get a toy or two and have fun exploring. Take up yoga or dance and free your body and your physical spirit. Being a feminine woman goes hand in hand with movement and flow and being bold enough to show this side of yourself off.


Get out there, climb the corporate ladder or build your business and be your badass self. But don’t forget to celebrate everything that makes you a unique, beautiful feminine goddess.

You can apply for membership with Cocktails & Conversation and receive 121 introductions with successful singles here 

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