From Flirting to Forever: It’s Time to Date Your Dollars.

Ashlee Cox • October 4, 2025

Dahlings, can we have a moment?


After all that deep, unscripted emotional labor we did last week—you know, the part where we finally stopped treating our bank accounts like a toxic ex who only calls at 2 AM—we made a real breakthrough. 


We realized money isn't the villain; it just felt like a fickle, commitment-phobic lover who we needed to renegotiate our relationship with. 


We accepted the current state of affairs and allowed the anxiety to flow with no judgements or desperate attempts to repress it, and  we affirmed for real, easy and consistent abundance.


 Vibe check? Pass.


Yet even after our spiritual breakthrough, I can't help but wonder: how do we actually make the relationship official?


Because, listen, an empowering mindset is fabulous, but it still needs a strong, supportive foundation to truly slay the day and keep you sane. 


And that foundation darlings, is knowing exactly where your cash is RSVP'ing every month.


The next step, in our navigation of our money relationship, Script-Breaker is simple, non-negotiable, and surprisingly romantic: We are dating our dollars.


Allow me to introduce to you, what I’m going to henceforth call the ‘Date Night’ strategy.


Oh, this is going to be funnnnn.


So, just as you wouldn’t commit to a man after one surprisingly soulful conversation over a martini during happy hour, you’re not doing that with your money mindset either.


For all my dating ladies, you know that the wooing part of the relationship begins with effort.


Dates are scheduled, questions are asked, you observe his habits, and then you decide if all of that is acceptable into your ecosystem.


 Your money deserves the same respect.


The unscripted way forward isn't just wishing for more; it's becoming intimately familiar with what you have and where it’s going. 


This is the ultimate act of self-love, and it only requires one dedicated Date Night a week.


Are you ready to go on a Money Date- possibly your first one ever? 


Let’s get down to it. 


First and foremost, the outfit, like on any date is a must.


You absolutely have to dress the part…the catch is instead of searching for your latest charming OOTD, you’re going to do this part mentally. 


So, light a fancy candle, let the scent permeate your space, feel yourself relax, and if it's your vibe, put on some chill background jazz or slow R&B music, afterall no one wants to be a nervous wreck on date night. 


Now comes the hard part, but I believe in you!


Open up a spreadsheet (or whatever awesome budgeting app you use).


This isn’t a punishment my darlings, this is a power meeting- and you’re the CEO.


Next, as you would on a date, take a good hard look at what is actually being presented to you, not what you think you should find.


This time, instead of it being a possibly attractive person at the end of your gaze, it’s going to be every monetary transaction from the last seven days. 


The $8 latte? The subscription box you forgot existed? The emergency pair of heels? 


Jot them down and just look at them.


Don't judge, just observe.


This may be giving you some grimacing/ flinching moments like watching a horror show, if the numbers start to look a little too real, but I need you to be strong and brave.


 Just observe them, and even welcome that uncomfortable feeling in your gut.


This right here isn’t about judging the spending or trying to figure out where to cut back,- no, this is about simply observing the reality of where your money spends its time.


A much needed background check if you will. 


So...still with me? Or is that a wine cork popping I just heard?


Put the glass down- okay, just a small sip, but we need to be sober for this.


So now that we’re aware of where the money went this week, it’s time to give your money a job.


That’s right, why should you have to do all the work? 


Every dollar needs a purpose, or a category- if you prefer.


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Don't Leave Your Money Date Mid-Sip!


You've done the hard part: you've faced the numbers.


 But the real shift happens now.


You need to assign your dollars a purpose so your cash flows toward your empire, not just random heels and lattes.


The rest of this post contains the crucial steps that turn mere tracking into true power including the single question to ask yourself to ensure your spending isn't sabotaging your life and how to use the facts you're going to gather to reduce anxiety and start building wealth!


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