“Let me buy you... ”
If you start your invitation with these words, you're responsible for the whole check. True, “dinner” is significantly less expensive than “dinner, plus three bottles of wine, then a cocktail and a cab home,” and you may be inclined to equivocate as such. Do not!
This part of speech is an offer: “come hang out with me, and I will pay for all your tasty pomegranate margaritas.” You’re incentivizing a stranger with the promise of free food & drink because you want to make yourself easier to potentially grope later, right? Right! That means you’re on the hook for any and all costs that lead to said potential groping. Now, you may not end up paying the tab for the whole evening; that remains to be seen. But at no point -- even if you moved to a bar, ordered a second dessert, or had to pay for valet parking -- is any portion of this first date the financial responsibility of the person you dragged with you.
Let’s say that no one kicked off this probably doomed courtship with the promise of free pommy margs. In that case, conventional wisdom states that the person who “initiated” the date is the one who should pay for it. This is largely true, but not without exception.
Location, location, location Like actual politics, navigating the choppy waters of check-coverage on a first date is a game. Unlike actual politics, the arena in which you “play” is a restaurant or bar, not a room in Washington DC with high ceilings and 535 old white dudes. (Hopefully. If you took your first date to Capitol Hill, you are undateable, and I cannot help you. Godspeed.)
What kind of place are you in: pricey or cheap? How formal are we talking here? What’s the “vibe?” Does it even “have” a “vibe?” These are the questions you must consider as you case the joint, for their answers are critical to your decision.
Generally speaking, if the restaurant is “fancy,” the person who suggested it is responsible for the bill. (For the purposes of this article, let’s define this as a loose combo of the following: $25 or more for an entree; one or less hamburgers listed on the menu; white tablecloths; napkins that people in bowties re-fold for you when you go to the bathroom; et cetera.) This is simply good manners. After all, you’re on a first date, which will, in all likelihood, lead nowhere. If you volunteer a restaurant where meals are a bundle, you’re also volunteering to drop said bundle. Period full stop. (Again, this isn’t to say that you will end up paying for everything, but you should be prepared to.)
However, if the place is not fancy, there are still plenty of oblique courtship machinations to be deciphered when the check comes. Onward!
Ordering: a delicate waltz Throughout the evening, take note of what your counterpart is ordering. The idea is to keep your own purchases within about 10% of theirs. This is as tactical as it is practical. To wit:
Tactically, you don’t want to leap way out in front -- or fall way behind -- your romantic interest’s order. If she calls for a Buffalo chicken sandwich, you should not then request a chateaubriand. But don’t demand a grilled cheese from the kids’ menu and desperately flail your expired college ID around, either. (Side note: where the fuck did you go for your first date, Dave & Buster’s?)
Why? First dates are all about finding common ground. “I could sex this person and not hate it” is what you’re aiming for here, and non-hateable sexing is based on perceived equality. Capitalism, on the other hand, is all about celebrating how much better of a person you are than people who have less money than you. Do you see where this is headed? Insecurity about money is not sexy, and drastically out-ordering or under-ordering is a sure way to instill it in your special friend. Getting approximately the same dollar amount of food is a good way to avoid this for now.
Practically, you’ll also want to keep your expenses closely matched throughout the meal. If you pull this off successfully, you have an escape hatch: you can each put cards down, split it evenly, and leave the Dave & Buster’s headed separate ways with little financial wear or anxiety to show for it.