ASK DU: To Pay or Not To Pay on a Date, That is The Question

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To Pay or Not To Pay on a Date, That is The Question

and We Answer!

In the second edition of Ask Urbanista, one male reader asks us to dish on the etiquette for paying on dates? Do you split the tab? Do you ask to wash the dishes? We provided our point of view:

Dear DU,

“Is my old-fashioned, chivalrous mind right in thinking that the first date is on me? Or, is it more custom to split the tab, at least at first. It sucks to mingle cash and relationships, but this issue has bit me before. I’m also a freelancer so trying to watch what I spend but don’t want to come off as a cheapskate.”


Mind on my Money


BrandyDear Mind on Your Money,

You are not wrong in your old-fashioned, chivalrous ways, my friend. This is danger zone 101. But while there are no hard rules, there are assumed social etiquettes. Let’s look at the types of date:

Formal dinner

First off, only do this if you can afford it because this is a scenario where you pay, bottom line. Asking her on a formal date and not paying is a sure path to Doucheville and looking like a cheapskate. To a girl, it’s like getting an invitation to a party and then being asked to cook the food. In my book, any invite (at least to something pricey) from either side assumes the invitee just shows up for fun. This applies to women, too. She asks, she pays. This can be tricky, but don’t get caught in the trap in this one if a woman offers to split the bill. This is the moment that you politely decline. Generally, most women who are offering to split the bill in this scenario are either one of three things:

a)  Doing it to be nice and not appear like a gold-digger (but still expects you to cover).

b)  Uber independent… like annoyingly so. (Run.)

c). She’s not interested and doesn’t want to feel bad about a free drink/dinner. (You’re still potentially in the game on this one, by the way.)

While the idea of a fake offer seems ludicrous, accepting puts you in the danger zone of being the topic of conversation during Thursday wine o’clock. Suck it up and fork over your credit card. While that may not seem fair, so aren’t glass ceilings, bleeding once a month and not dying, and having punching bags as genitals. We all have to pay our dues.

Drinks at a bar

This is where you can breathe easier. If the date is more casual, I’m generally okay with splitting on the first date. It would be a very nice gesture if he paid, but I wouldn’t be insulted if he didn’t because it was casual, a meet-up, the prerequisite to the real date. If you go on date #2 and #3, however, don’t make splitting a habit. Somehow sitting side-by-side verses across from each other changes the formality, but if you really like her and sense that she likes you… pay with glee.

My advice, Mind on Your Money, keep the first few dates simple and in a zone where you can afford it — drinks at a local pub, Sunday custard, coffee, and start to feel out what type of woman you’re dealing with and her expectations about dating. If you’re hoping the splitting thing has become the new etiquette because your wallet would thank you, it hasn’t.


LauraDear Mind on Your Money,

I am probably the LEAST appropriate to respond to your question. I hardly go on dates.  Oh hey now, maybe we can kill two birds with one stone.  Meet me at Siena Tavern, 6 p.m. My treat.



Hi there,


First off, take Laura up on that offer, homegirl needs to go out more (with dudes) and you’ll both benefit from the evening. (Brandy champions this.)

Secondly (and more importantly) I’m with Brandy on most of what she said. It’s been drilled into my head that the guy always pays, no exceptions. However, as I’ve gotten older and developed a more refined (and almost always expensive) palate, I began rethinking what I’d been taught. While chivalrous, it wouldn’t be fair to my date to pay for lobster and filet mignon on the regular. So nowadays, if I ask someone out then I expect to pick up the tab, and visa versa. Well, I don’t expect the guy to pay if he’s the one doing the asking, but I hope. This is also why I always carry some form of currency when going on a date. And if I can’t afford to eat somewhere then I’ll make other suggestions, just in case.

This is across the board, informal or formal, you’re inviting someone to meet you. Pick up the tab. 🙂

As you move past the first 5 dates things change a bit… splitting the bill or “I’ve got this one” should become more common, and that is OK.
LisaI hate myself for saying this, but yeah – you should make the move to pay and if she offers, let her pay a small portion, like the tip, or drinks afterwards or whatever. I think most (non-sucky) females I know are fine with things being equal later on, but I think they’d be turned off of a guy who didn’t offer to pay on the first few dates. That being said, just think of something cheap/fun. If she’s offended by the fact that it’s inexpensive, then she probably sucks.

True story: one of the best first dates I ever went on was to the Wiener Circle on a mission to discover whether or not the whole “chocolate shake” thing was real. Proof that a date doesn’t have to be expensive to be good. Personally, I’ll take funny over filet mignon any day.


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This post was written with love by the Daily Urbanista team. Have a question for us? Say hi on Twitter: @DailyUrbanista or shoot us an email: [email protected].

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