I slipped my shoes off just inside the door. Pulled my water bottle out of the fridge and stood, lit by the glowing blue of the fridge interior, chugging: “Probably going to regret that last glass of wine tomorrow.”

But in the moment, I didn't. It was the first date in a long time that I had gotten home, hoping I'd see him again. The conversation had flowed easily. We'd jumped from one spot to another, hands sliding together between locations and then, with the touch barrier broken, our bodies slowly growing closer throughout the evening.

Confident Woman Drinking a Glass of Wine in bed wearing a robe

Replacing the water bottle into its spot inside the door, I began my evening routine. Brush teeth. Face wash. Dry my face. Retinol (hello 30!). Moisturizer. As I go through the motions, thoughts not required from years of repeating these same steps, I scan through memories from the evening.

This was not one of those dates where I wondered if he liked me, mostly because of his initiative to kiss, his unsolicited comment, “this has been really fun.” But I know that fun did not a relationship make. 

In the days that followed, a few texts were exchanged. Conversation sweet but not consistent. The doubting thoughts crept in - “Did I seem too eager?” and “Why isn't he putting more effort?” But as soon as I could switch the topic in my brain back to the task at hand, whether it was folding laundry, updating my bookkeeping spreadsheet or making it through airport security, the feelings of doubt and self-questioning dissipated. My day-to-day confidence returned and the clouds lift.

This experience is not rare. I know how often it is that an accomplished, competent woman can navigate intense business negotiations at work without feeling unmoored but the oddly worded text from a guy she's seeing can have her discussing via screenshot with three friends. 

Why is does dating seem to be such a kryptonite for the confidence of high achieving women?

Of course, matters like these are always personal and layered - certain things playing bigger roles for certain women - and the experiences that led to this pattern as unique as the woman at hand.

But in my work, so often I notice that women who have climbed a corporate ladder, gotten a hard to get job or reached a high achievement level in perhaps a musical instrument, an athletic endeavor or so on, pride themselves on understanding the system. Knowing how to present themselves to have the head honcho take seriously their ability to represent the firm, even at their “young” age or having mastered a rehearsal routine such that their dance skills were noticed and rewarded. 

I understand how this works and because of that, I succeed. 

And then when this same woman navigates her dating life, the system confounds her. Some men seem to enjoy a date and continue to pursue, others speak of hanging out again and then never reach out. A dating app prompt seems to elicit interesting conversation for a while and then dips off. This cycle begins, every time she gets a new piece of data to work with, in the form of a match, a date or a text and when she also happens to like the guy, it becomes mission critical to make this new information make sense within her current evaluation of how the system of dating works. Because especially now, that there's a specific person in front of her she likes, she wants to succeed. 

Even in my line of work, supporting with so many high achieving, caring, objectively impressive women who are struggling with what feels like “situational confidence,” I too also fall prey to this same behavior set and notice, as I did, in the above real description of my life. 

Journal laying on white linen blanket with gold pen confidence journaling

So what is there to be learned from this very common pattern?

In my opinion, it comes back to responsibility. In professional settings, a successful woman is clear on what she needs to do in order to show up well and which parts of the equation are outside of her control. Prep the documents, present a clear argument, answer questions calmly. If the company shifts its priorities for Q1 and the project falls through, disappointing but not a personal fault. But in dating, this woman has a tendency (guilty as charged!) to assume responsibility for more than is hers. He didn't text back, I must have said something that turned him off. He said he had fun and then is slow playing the messages, he must not find me that attractive.   

The sense of responsibility that makes her/us so successful in other parts of our life, when applied to a system where cause and effect is less clear and “the way things work” varies dramatically person to person, often creeps beyond reasonable bounds to try to return some semblance of control.

Because if you assume the cause of the unexplainable behavior is you, then you can do something to shift it (and therein lies the cause of so much pain). 

But my dear friend, you are not responsible for a man (or woman) getting stressed at work and deprioritizing checking his Hinge. You are not responsible for someone's emotional readiness to date or the length of time since their most recent breakup.  

So what is to be learned? As frustrating as it is, focus on the inexplicable. You were able to manage the uncertainty of not knowing where you were going to college for weeks if not months. It wasn't necessarily enjoyable but you knew an answer and clarity would come eventually. The same is true here. You are already qualified, so to speak, so go live your life. As best you can, settle the spiraling thoughts with a reminder - I can't know what's going on in somebody else's head but time will give me more information and I can handle whichever the outcome is. 

Dating is not a test to pass and having someone not call you back is not an indicator of your worthiness. I know reading that sentence incites some argumentative thoughts but I’ll save that topic for another day.


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The first step to being more confident

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What are your priorities right now?