Hmmmm...maybe dating sites could have a financial literacy test, and we'd all know each other's score on that?!:) Though I believe discussing finances is important, I still feel very reserved broaching it. As a woman, I worry--perhaps stupidly--that if I broach the topic, I'll be accused of being a gold digger. I want to convey, "I'm not asking because I'm after your assets; I'm just trying to be sensible to make sure I'm not becoming attached to someone who doesn't match me in this area." That's not the most romantic declaration:) I so feel for people after the 2008 recession who, through no fault of their own, lost so much. They may not look, on the surface, as financially stable, but, as you said, as long as there are transparent conversations about why they've ended up in the financial pickle they're in, and what you're doing about it, then that's a great starting point. Any tips on how to broach this topic with someone, without making them feel 'bad' for their financial position, are welcome. Even the most gentle wording and tone can still make these sorts of conversations go awry!