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After all, even in our evolved world, the man expects — and in some cases is expected — to pay.“Let him pay at least the first two to three times, and then on the third or fourth date by all means if you want to, absolutely offer to pay the bill,” says relationship expert Kailen Rosenberg.

You’d want to know if your steady’s trying to pay off a six-figure law school loan or hasn’t saved a dime towards retirement yet, right?It’s easier to rationalize that “we’ll try harder” and “things will get better” than to pack up and walk away. At some point, as a relationship grows and becomes more serious between two people, questions begin to arise about long-term plans, particularly as it begins to become clear that at least a significant portion of two lives are going to overlap and become one. This simple question is a lot more complicated than it looks: Not surprisingly, the typical personal-finance “expert” has a pre-prepared piece of advice handy: “Always talk to your partner about their finances! ” Uh, yeah, that’s a nice theory, but most people don’t talk to their partners about money for months, if not years. If it was CC debt for frivolous purchases, that’s an entirely different thing.We mused about kids a bit, with a general consensus of waiting for a least a year after our wedding. For most of the first few years of our marriage, our financial planning and organization was chaotic at best.We were often doing things in completely contradictory ways, like making separate grocery lists and both shopping on our way home from work, or refusing to budget or merge checking accounts because we both wanted control.Picking up the bill is about “power in a relationship and how men and women want to think about their roles,” says Galena Rhoades, Ph.D., professor with the Center for Marital and Family Studies at the University of Denver. On this particular afternoon, he went to meet her for a quick coffee/lunch because he had some spare time. She decided that she wanted to eat at a pretty expensive restaurant. He offered to take her for some fast food (or something quick).

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