My bf has no retirement either, and no financial sense. But I don't consider it my problem. I stay with him because I like him. But I may not want to actually get married, since I'm not interested in splitting half of my assets with him. However, since our money is separate, I don't care how ridiculously he spends his own money, even if he's already broke.
I certainly would not argue with him about it. It's his money, do whatever he wants. If you like him, stay with him, if not, break up. Seems pretty straight forward. I personally won't let finances enter into the decision.