I'm a sucker for websites that contain posts about dating disasters, as they are like car wrecks but at least no one gets grievously injured unless of course they're dating R&B artist Chris Brown. (Yeah, I went there, Chris Brown! And you can't smack me because I'm not dating you) There seem to be a lot of recurring themes with dating disasters--guys getting too drunk on the date, guys with serious anger issues, mothers tagging along on dates--but one seems to stand out a lot. The money issue! This story is a good example of that (and also see the controversy in the comments thread below the post)
See, in these modern times there's a lot of back and forth as to who should pay for what and how it should be done. Guys wonder if it's considered paternalistic to insist on paying for everything, women wonder if it's a turnoff if they insist on paying part or all of it, and no one is really sure that the other party is okay with it. One of my female friends who I knew both in D.C. and in Portland--a good looking woman with a lot going for her--told me she always insisted on paying her share on first dates; most of my guy friends tell me they'll never allow the woman to pay for anything, no matter what. It'd be interesting to set her up with one of them and see who wins!
Seems to me though that there is a basic rule--on the first date, the guy should be prepared to pay for everything.* There are two complications: (1) What if the woman was the one who suggested the place or invited him out? (2) What if the woman makes as much or more than he does? It might seem unfair for a guy who works as a waiter while in school to be paying for a fancy dinner and show when the settings were suggested by the wealthy corporate attorney he is going on the date with.
My take on that is he should still plan to pay, as of course if he truly can't afford those costs for one evening then he needs to suggest instead plans that he can afford. (And if you're being treated to a meal? Then you DON'T BITCH ABOUT GOING TO CRACKER BARREL. YOU EAT YOUR CHICKEN FRITTERS AND ENJOY THEM!!! Nothing's more annoying than the woman who posted her worst date being the guy who took her to Burger King after the concert that he paid for. Lady, did you offer to treat for a nicer more "acceptable" place? No? Then kindly enjoy a glass of Shut The F__K UP).
Now, when the guy takes the bill or pulls out his wallet, the woman has a duty to reach for her own cash--suggesting that she pay for her share. This is important, because it signals that she doesn't feel entitled to be treated. However, the guy must politely insist on paying, at most suggesting she can get them drinks later, or pay just the tip, if she's insistent. But at that point the woman should relent. Otherwise you have a long discussion about who should pay, social conventions, and at the end of the day it's really not that much money. If you never see each other again, it's a minor thing. If you do see each other again, you'll have plenty of time to make things even.
*(Of course, once you're in a relationship it can become more equitable, since there are many opportunities for each person to treat, and it can be based on who has more to spend, who insists on fancier places, all that stuff. These rules are more about initial dates)