I tell men before our dates that I’ll be paying for dinner. This is apparently clear information right up until I pay for dinner.
Until then, things usually go well. We’re enjoying ourselves, the meal is good, and nobody seems particularly distressed. Then he realizes the bill has been handled, and suddenly the evening has a problem.
I’m 43, live in Oklahoma, and am independently wealthy from a company I started myself. I’m also a chef and sommelier, which means my idea of a nice dinner tends to involve courses and wine chosen with some intention. If I’m going out, I want to eat well. Applebee’s and I can maintain a respectful distance.
Those are my expensive tastes. I don’t expect a man I’ve just started dating to fund them. Paying seems like a reasonable way to enjoy the experience I want without handing someone else an obligation along with the menu.
I’m quiet about it, too. I usually take care of the bill privately before dinner starts or sometime during the meal. There’s no ceremonial presentation of my credit card. I’m trying to buy dinner, not unveil a hospital wing.
And yet men get irritated. Sometimes angry. Sometimes I don’t hear from them again. The timing is what confuses me: it’s generally going well until they discover that I have, in fact, paid.
For context, I date men roughly 35 to 55. There aren’t many men with a higher net worth in my area, and perhaps Oklahoma’s more traditional dating expectations play some part. I’m still unclear on which tradition requires being warned about a free dinner and then objecting when it arrives.
I’m also polyamorous and have been married for 17 years. I date separately, and everyone knows that long before an in-person date. That information is already on the table. The bill is what seems to cause the late surprise.
I keep hearing that women who want nice dinners early on are gold diggers. I thought covering the cost myself would settle that particular concern. Instead, I’m having lovely meals that can apparently end badly because nobody asked my date for money.
I’ve explained the arrangement in advance. I’ve paid discreetly. The food has held up its end. What am I missing?
