It has been said that the psychology of money is more complex than the psychology of sex. Having said that, especially if a relationship moves to a greater state of commitment, do not assume anything. Speak openly about your concerns and see how disparate your lifestyle expectations and spending behaviors may be. For instance, don’t assume that someone who may be chronically unemployed is going to work and if having kids is being discussed, make sure you’re on the same page when it comes to work and finance expectations. Sometimes men will pursue a woman who makes more money with some unrealistic ideas about being supported. Most women still (over time) resent carrying men and it’s not uncommon for women to feel that “your money is my money and my money is my money”. However untraditional she may be, I have found that most women do not want to support somebody (let alone pay spousal maintenance to them!)