I would say have mini-talks the whole while you are regularly dating. When I say mini-talks I mean the light but probing questions that give you a little bit of insight. But the "big" talk needs to defnitely be at the point in your relationship when you find yourself getting serious with the person and BEFORE marriage. I didn't do that and I wish that I would have. Even if one of you has problems, it at least gives you both time to plan a financial strategy before you make that type of commitment. It makes things much easier. But you live and you learn. I am just learning this at 35! I should have known it years ago. That is the one thing I do stress to my daughter since she has left home for college. When she meets the right person that she is thinking of settling down with, she should never be afraid to discuss these types of things. It's just as important as asking someone their career path or how many children they want to have. People are less reluctant to ask those types of questions, but are very sensitive about discussing finances. All of those things are intertwined.
Starting over in the garden...my seed has been planted:-)Last app: 02/23/2013