Modern Dating Debates: Who Picks Up the Tab? 

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Alt text: Flat lay of a handbag, makeup and similar items. Image source:
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Meta Description: Who should foot the bill? This millennial author shares her personal experiences and views. Learn how this seemingly simple question can reveal much about your date and yourself. 
Picture this scene: You're out on a date, laughing as you trade embarrassing stories, clinking glasses, and trying not to let on that you've got a weird fascination with conspiracy theories. 
The night's going great...until the bill lands on the table, and the atmosphere thickens like your nan’s homemade stew. 
The million-dollar question looms in the air: "Who's going to pay?" 

The Millennial Dilemma: To Pay or Not to Pay 

When I first waded into the dating pool in my 20s, I was like a fish out of water when it came to settling the check. 
Fast forward to being a millennial in my almost-30s, and I'm juggling thoughts about smashing the patriarchy, championing equality, and of course, the eternal conundrum: how to make avocado toast without smashing it into guacamole. 
Jokes aside, I’m all about gender equality. And yes, that extends to the much-debated topic of date expenses.
Expecting the guy to whip out his wallet every time the waiter leaves the bill is as outdated as asking your date ‘A/S/L?’ – what is this, MSN Messenger Circa 2005?
Today, as we embrace gender neutrality and break down traditional stereotypes, it's high time we revisited these age-old dating norms. 
Can a woman pay? Of course! 
Should a man feel obligated to pay? Not necessarily! 
Let’s get into the nitty-gritty of why I think this is the case.

Men, Money, and The Silent Messages

Let's be real: men shouldn't always have to pay. 
But here's a little insider's secret - how a man handles that moment can speak volumes about him. It's not about the ability to flash cash but rather, his approach to money, his take on traditions, and even how much he’s enjoyed your company.
Take for example that chill bloke who casually suggests going Dutch. Or, the gent who insists on paying because that’s the way he was raised. Or maybe the guy who painstakingly counts every penny because he "forgot his reading glasses" (Yep, been there).
Each scenario tells a story. And really, isn't that what dating is about? 
Each interaction, each gesture, each smile - they're chapters in your shared narrative. These silent messages might just help you read between the lines, discern the character behind the charm, and add some unexpected depth to that cheeky pint and plate of nachos. 
After all, dating isn’t just about finding someone who checks all the boxes; it's about finding someone whose story you want to become a part of. 

The Art of Offering and Accepting 

A man offering to pay is, well, actually rather nice. It's not the act of paying that pleases me, but the gesture – of goodwill, of generosity, of interest. It shows he's invested (pun intended) and that he's enjoyed the evening enough to slap his Amex on it.
Interestingly, there's something to be said about how accepting this gesture can play into our feminine energy, too! 
At times, allowing oneself to receive – to accept a man's goodwill – can be a powerful affirmation of femininity, just as an offering can affirm masculinity. The dynamic interplay between giving and receiving, much like the yin and yang, brings balance to our relationships. 
It's not about dependence or submission, but rather about appreciating and understanding the nuances that make our interactions more meaningful.
The caveat is that this should never be an expectation, and it should never be a one-way street. I've split bills, and I've even footed the entire thing (much to the surprise of several dates). 
At the end of the day, it's all about equality, freedom of choice, and setting our own rules.

Wrapping it Up: Who Foots the Bill?

Here's the bottom line: In the grand scheme of life, love, and all things dating, who pays for your mozzarella sticks doesn’t really matter. It’s just a bill–regardless of whose wallet it comes from.
So, the next time you find yourself in this all-too-familiar scenario, take a beat. What feels right? What makes sense? Remember, it's all part of the rollercoaster journey of navigating modern dating and finding what works best for you.
As we pick up the tab, and the conversation, next time, remember one thing: if he doesn't laugh at your jokes, he's not worth your tiramisu. 😉
How about you? What’s your take on this modern dating conundrum? Let’s keep the conversation going. Share your thoughts in the comments below.
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Posted Sep 26, 2023

This opinion piece was written for a client whose focus is to encourage money talk in a fun, explorative manner.

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