The Financial Cost Of Being The “Chill Girl”

February 17, 2026

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By Alexa Claire Brooks Major, TFD Content & Production Manager

May I be vulnerable with you?

Last year, I let one of my friends be my “dating manager.” It resulted in 14 first dates, five second dates, one date turned new friend, zero new boyfriends, zero new girlfriends, and a massive realization: being the “chill” girl is expensive — in more ways than one.

While it’s known that dating can be expensive, I don’t see enough talk about how costly dating personas are for women, especially given that we seem almost required to bear them. 

We’re all familiar with the rules: to be “chosen”, a woman must master wearing the mask that grins and lies. She must become so skillful at it that she begins to believe the ruse herself, no matter the consequences to her person or her wallet. All for the benefit, ease, and convenience of the man she’s “hoping to lockdown”. It’s especially trying because it denotes a narrative that being chill or low-maintenance is neutral — no harm done — when, in actuality, that couldn’t be further from the truth. We are tired, and our bank accounts are begging for release.

The financial penalty for being the chill girl is real. How often have you (or a friend!) consciously or subconsciously started molding yourself into a certain guy’s ideal woman? Typically irksome behaviors started to be excused. “Oh, he’s 30 minutes late to the date, it’s fine! No problemo! I’m chill.” Even though you know that this will likely mean you’ll need to feed the meter more than you planned, or that the date will end too late for you to feel comfortable taking public transport home. Perhaps you’ve ended up feeling like you needed to order an additional drink than you’d originally planned because sitting idly, solo at the restaurant, as you waited for your late date would feel too awkward.

All of this shows up in your budget. It did for me!

And amid the 14 first dates of last year’s summer dating spree, I also had a whirlwind romance that kindled (off the apps!) in a West Village clothing boutique and ended in the ashes of ghosted paragraph-long texts. Long story short: they lacked the capacity to show up for anything deeper to blossom between us — despite claiming they wanted it. But I have no regrets. I’m more grateful than anything, really.

I also kept thorough track of just how this impacted my finances. Throughout our three months of dating, growing closer, and ultimately (I thought!) falling for each other, I was keeping a close eye on my Monarch Money account. I made a custom main dating category and added subcategories that fell under that umbrella: entertainment, beauty, clothing, restaurants. This way, I could properly track how much this dating manager/client experiment my friend and I were running was costing me, both directly and indirectly. 

Even though nearly all of the people I went on dates with were adamant about paying for everything, the numbers didn’t lie. I’d spent nearly $400! Not an alarming amount (I have friends who’ve spent far beyond that that have similar take-home pays) but its effect on my budget, especially my progress toward my financial goals, was evident. If you read my last newsletter, then you know I’d started saving for my move to New York by this point, and every penny counted. I’d worked hard to mediate my insecurities, but here they were, popping up in a whole new way that was affecting my future aspirations.

I thought I was being empowered and taking a break from being the uber-prepared older sister, family manager archetype I’d been so accustomed to fulfilling. Of course, two things could be true: I was being brave by putting myself out there (a genuine goal of mine) and I’d been unconsciously editing myself. 

Clearly, I’d been subject to the sneaky “chill girl tax.” That slow, creeping penalty we pay for matching someone else’s lifestyle, attempting to align ourselves with what we perceive their expectations to be so we can be easily, perfectly…chill. 

I wasn’t just spending more money. I was spending more of myself. And I was tired.

Hair, nails, makeup, clothes…even just spending more on the cheaper versions of these items! From switching out my nail glue-ons more often than I normally would to going on extra visits to thrift shops, the chill girl tax can take effect in all sorts of ways. Heck, I even spent accidental money on lapsed free streaming trials because I wanted to check out some show a date had mentioned to me. I also spent money on weekend plans, like going to the museum, because I didn’t want to respond to “What are you up to this weekend,” with, “Oh, same old, same old.”  It’s a penalty no matter if you’re splitting your bill at the café where they got more pastries than you did or at a five star restaurant. If you’re spending money for the purpose of presenting a version of yourself that you believe your dating partner would prefer and makes you seem as though you’re up for anything, it’s the chill girl tax at work.

And, what’s worse is, I wouldn’t have known I was paying it without tracking my spending. All the transactions that led to that $400 total were so small they were hardly noticeable; $5 on a coffee here, $20 on drinks there. I’d made the customized dating categories because of the dating manager/client experiment with my friend. I wouldn’t normally have done that. Tracking my expenses in Monarch quite literally uncovered insights into the behaviors I’d been embodying — consciously or not — while dating and I was thankful for it because, now, I could do something about it.

So, what does spending while dating look like for me now? In the past three months, I’ve spent just under $200 — 50% LESS than 2025’s three-month summer dating spree. Which is especially saying something because winter is usually my time to SHINE in the dating scene.

The transactions that went into this feel comfortable for me. They feel like expenses that were made for Alexa, not for keeping Date #43231’s attention. Turns out, the most attractive thing I can be isn’t chill — it’s aligned. I’m no longer subsidizing a performance to prove it.

Happy Valentine’s Day to me!

FEBRUARY 18: As mentioned in the intro to this newsletter, we’re hosting a free workshop TOMORROW! Join Chelsea & licensed financial advisor, Kellen Thayer for How To Financially Prepare For An AI Driven Future. As AI, layoffs, contract work, and an increasingly unstable job market have made the idea of a “steady paycheck” feel more fragile than ever. Many people are navigating real fear about being replaced, downsized, or forced into more volatile work—while still trying to build wealth, protect themselves, and eventually retire. This workshop will focus on how investing and financial planning should adapt when income feels uncertain or at risk—without resorting to extreme risk-taking, constant market timing, or freezing out of fear. The goal isn’t to predict the future of work, but to build a financial strategy that can hold up even as the system becomes more volatile. We’ll break down what traditional advice still works, what needs to change, and how to build real resilience into your financial plan so you can keep investing, growing wealth, and creating long-term stability—even in an unpredictable labor market. Take our short quiz to register!

Join Chelsea along with some very special guests for How To Take Political Action 101 (date will be confirmed soon!) — Scrolling social media can leave us feeling angry, frustrated, or powerless—but it doesn’t have to stop there. Our hosts will share expert insights on how to take meaningful political action without feeling overwhelmed. This workshop will show you how to channel your energy into tangible steps, from local and national engagement to effective communication and sustainable involvement. You’ll leave with a practical toolkit for turning concern into real-world impact. This workshop is designed for anyone who wants to move from frustration to action—whether you’re new to political engagement or looking for ways to be more organized and effective. Be the first to know when registration opens. Drop your email in this form so we can notify you directly!

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