Check, Please! Who Should Pay on the First Date?

The vibe at Captain Gregory’s is perfect for our first date. The Paradise Found cocktail I’m sipping is going down easy – almost as easy as my date is on the eyes. We laugh, we flirt, we order another round. Everything is going great…and then the bill comes. Do I offer to pay? Do I go halfsies? Do I make no motion for my purse at all and let him pick it up, no mistake??

Money and dating can be tricky, especially as a financially independent and successful woman. To help take some of the angst out of it, I solicited Erika Ettin’s input. Erika is founder of A Little Nudge, a dating coaching service specializing in online dating. She is a sought-after dating expert, and you can follow her on Instagram @alittlenudge. I snagged a few minutes with her to hear her thoughts regarding money and dating.

Lauren: Is there a rule of thumb when it comes to who should pay on a date?

Erika: Oy! People are so confused these days… There isn’t a rule of thumb out there, but for opposite-sex couples, I generally advise my male clients to pay and my female clients to make the offer. Of course, like most things, there are always exceptions to the rule. 


Lauren: My feminist values went on red-alert – are we continuing traditional male (and, by connection, female) roles? Or why is that?

Erika: I think there’s room for feminism as well as gestures of generosity. In general, the person who is asking for the date should be paying. In the U.S., in most cases, the man is the one asking. [Paying is] a nice gesture.

I will say whoever pays for the date -- it shouldn’t have anything to do with who makes more. The first date should be something simple, so there shouldn’t be too much anxiety about how much the date costs anyway.


Lauren: Does it change with date #2…#3…etc?

Erika: I find splitting the bill somewhat tacky and tends to put people into the “friend zone.” Before a date, whoever is going to pay can certainly give a signal – “looking forward to tonight – it’ll be my treat!”


Lauren: You mentioned splitting the bill can be considered tacky. To me, I agree that it feels very “friend zone.” Is there an appropriate place for this?

Erika: If people prefer that, that’s fine for them and nothing wrong with it, but it just isn’t the advice I give.


Lauren: In your experience, when is a good time or what is a good way to bring up money when you’re continuing to date someone exclusively?

Erika: That is completely up to the two people – when you feel comfortable is the best (and only) time to talk about it.


Lauren: Any other thoughts to share?

Erika: As I mentioned earlier, people are just confused these days. For every woman who wants a guy to pay, there’s a woman who expects—and prefers—to split the bill. 

Lauren: Sounds like allowing for some grace is key. And stating things upfront can help relieve the anxiety felt on both sides about it?

Erika: Exactly.


At Captain Gregory’s, in the end, I didn’t make a move for my wallet. I let him pick up the tab, and I quickly followed up with “I’d love to treat next time” – not just for the financial gesture, but to show how excited I was to see him again! And, at the crux of it, isn’t that the only thing that we should really be thinking about?

This communication is for informational and educational purposes only. No content or reference is intended to be a recommendation for the sale or investment in any product, strategy or service nor should it be perceived as individual advice. Please seek the advice of a financial advisor regarding your particular financial situation.

Visit xmlfg.com for more information. 


See Also: The Language of Money – How Fluent Are You?

Lauren O’Brien, CFP®, RICP®, CPA

Lauren serves as Senior Wealth Advisor at XML Financial Group and maintains the credentials of CERTIFIED FINANCIAL PLANNER™ professional and Retired Income Certified Professional®. She’s on a mission to make money more conversational and empower women to financial success. 

She was raised in Northern Virginia before obtaining her business degree from the University of Notre Dame. Following stints in Chicago and London, she returned to the DMV and happily settled in Old Town. 

You can find her at home cooking a new recipe, at a wine tasting in town, or delving into an Excel spreadsheet. She is an avid traveler and aims to finish her quest to visit all 50 states this year.

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