Hey StockTrader,
While going thru my divorce, I was also going thru Ch11, then 7 with my company. From a millions to nothing in a few years. Currently building another business, so I am always broke too (For more detail you can check out my thread "A field study on attraction, afc, and being a man.")
Anyway, here is the thing now. First dates are always meeting for coffee, or I suggest they "make me dinner and try to impress me." So you understand I had 2 dates on Thursday, one coffee for about an hour, right after that another girl made me dinner at her place, then had a girl come over Saturday and cook me dinner at my place. All girls I had met in the last week. I do not "take girls out." Just have fun with it, and come across as "you judging her BEFORE you will spend your hard earned bucks." Think of it this way, every other guy in the world does not have game, so they feel they must invite them out. Change the frame....... You ARE SO MUCH THE MAN, she must earn your time. After the first date of dinner, invite her to your place for a cup of coffee and a walk at sunset. You know, tell her "I really enjoyed your conversation, and I would like to talk to you some more. Why don't you join me for a walk this evening?" Try to imply you are going for a walk whether she joins you or not. Now usually, I have them hooked at this point, and money isn't an issue. I also like to hike, so I take them on these types of physical activities. The worse thing you can do as a DJ is buy her dinner on the first date......... it is a totally wrong frame.
Oh, if you become attractive to her by doing all the things you should learn on here, she will start paying for you if she can, or doing what you want. It's not the buying them, it's being more than the other guys.
Good luck........