Unless you're insanely poor (in which case maybe dating isn't the best idea at the moment), the idea of not paying should not stem from some weird obsession with pinching pennies and being a cheap ass. I hear guys brag about how they will absolutely never will pay for a date. That seems silly. My rule is to just keep the date under 30 bucks.
First off, if you build some strong chemistry and IL before the date, there's no reason it will likely be a flop. Even if you don't end up banging her, having a chick to bring out with her girlfriends will help your social proofing. Being a cheap ass will not.
Second, a lot of times the chicks end up paying for stuff the next time anyway. If you're a cool enough dude, you can get them to pay for stuff. I'm not saying this should be the goal but the point is that the ROI is higher.
Some chicks--even the NON gold digger *****es--just feel good when a guy pays, even if he just buys a drink and a cheap appetizer. It's not about the amount of money. Taking an absolute attitude to not paying is most likely closing off your options to tagging more chicks. Plus your ROI might even be less.
There are some dates that I just won't pay for because I KNOW that I can't stand the chick and don't want to talk to her again. But if she's cool and we're having a good time, I wouldn't be a penny pincher over 20 bucks. All it really shows is that you're a cheap ass.