I grew up with a fairly clear set of instructions for dating: bring flowers, open the car door, pay for dinner, and walk her to her door. Being a gentleman came with a checklist, and the check was on it.
Paying was presented as part of the occasion. I wasn’t taught much about discussing it, because there supposedly wasn’t anything to discuss. The bill arrived, and the man handled it. A beautifully simple arrangement for anyone who wasn’t the man’s bank account.
I have a stable career, and I can afford to pay for a few dates a month. Buying dinner isn’t automatically a hardship, and I don’t resent treating someone. But I also don’t want to feel that paying is the permanent price of admission to spending time together.
What I can’t quite figure out is how to bring up sharing the cost. Expectations seem less uniform now than the ones I grew up with. I don’t know what a woman expects, and she may have no idea what I expect, either.
Even the wording feels awkward. Asking someone to split the bill is straightforward in theory. In a dating context, I wonder whether it sounds casual, considerate, stingy, or like I’ve just announced that the evening failed its financial review.
I’m interested in how this actually goes between people. Men, when you’ve asked a date to pay for herself or take a turn treating, how did you say it? Women, has someone brought it up in a way that felt comfortable—or handled it so badly that you immediately lost interest?
I know how to reach for the check. I’m trying to figure out the sentence that lets us have a conversation before my hand gets there.
