Almost everyone I know has (or at least had, when he or she was single and dating) a very complex set of rules and regulations when it comes to how money is handled on a date. Rules about who pays and why; if money should be offered and what that means; if that money is accepted, what that means; at what point along the dating continuum money no longer becomes an issue, etc. The unfortunate thing I’ve noticed, based on entirely non-scientific methods, is that each individual has his or her own set of rules and regulations. This creates a great deal of confusion. A seemingly basic first date scenario may go something like this:

Boy asks girl out for drinks.
Check arrives.
Boy and girl reach for wallet.
He says, “no — I’ve got it.”
She says, “are you sure?”
He says, “yes.”
She says, “thanks.”

Seems okay, right? Wrong. So many variables can come into play that apparently mean different things to different people. Some guys have told me that they are upset when women offer to chip in because it means they’re not really interested in a romantic relationship. This is crap. Many of us are offering to pay because we don’t want to feel obligated or to “owe” you anything. It’s the first date, for chrissakes. Some of us are offering to pay because we’re polite — that’s the way we were raised. Some guys get annoyed when women don’t offer to pay. “They should at least offer,” I’m told. Hear that, ladies? Once we’ve offered up some cash, are guys allowed to take it? “Sure,” I say, but this is not a universally held belief among my female counterparts. Some women are offended when a guy takes the money. “He’s not supposed to take it!” Confused yet? I know I am.

According to my rules, if I ask a guy out, I will always offer to pay for both of us (I ask, I pay — my variation of don’t ask, don’t tell). If he asks me out, I will always offer to contribute to the bill, and will not be hurt/upset/offended if he takes the money. I will generally only insist a few times on my offer, but this depends on whether or not I like the guy. If he refuses my money, and I’d like to see him again, this is a perfect segue, “well, I’ll treat the next time.” If he refuses my money, and I have pushed a few times, and I don’t want to see him again, then screw it — I offered, not my problem anymore. I work for a nonprofit — I’m not rich — I’m only going to insist so many times.

At some point in a relationship, who actually pays tends not to matter so much — it all kind of evens out in the end. I’ve forgotten what that’s like. Hmmm.

So, dear readers, what are your rules?