Can you still have a great time with a poor guy? But if you offer to drive, he feels like less of a man. If he is poor, he is probably only partially employed—if employed at all. It might not be read as just a nice gesture—as it would be if the guy could afford to pay—but rather as a pity gesture. He is probably subservient to somebody at his job, i.
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Trust me I have seen first hand, and it breaks families. I had a conversation with a friend last week about this subject and he told me I was too picky. He even said that he would marry a waitress; I told him I wouldn't and he looked at me as if I was crazy. I want to marry a woman who is independent and who would be more of an asset than liability.
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But money can certainly cause tension and stress in a marriage — depending on how much or how little you have and your attitude on spending it. Growing up, money was never an issue in my family. My parents owned a successful business that abundantly provided for our family. We traveled frequently and lived very comfortably.
Although diamonds make a girl's eyes sparkle, you can impress a woman even if you are poor — sorry, financially challenged. So keep your head up, and your wallet intact. I will be realistic though; of course there are women out there that would never date a poor man, much less talk to him. There are gold diggers everywhere, but if she doesn't want you just because your bank account doesn't match her shopping budget, chances are you wouldn't want her anyway.