If you want to date one or more people at a time just to have fun, carefree experiences, knock yourself out. Spend whatever you've budgeted for the ladies. Have a great time!
But if you're looking for an intimate relationship and perhaps something more long-term, let's assume you want to be with a woman who's with you for you -- not your money (or lack thereof). It's fairly easy to have a good time with almost anyone when you're doing fun things like dining at nice restaurants, attending swanky events or living the high life. Right?
So, find out if you two have a close bond by doing free or cheap things together. If you're able to feel closeness and have a blast without spending a dime, what's holding you two together probably has more to do with your dynamic than you simply being a vehicle to fun times.