Since money is so taboo, no one really tells us how to have these discussions , or when is the appropriate time to start talking. "Is the first date too soon? Is the 10th date too late? Do you bring it up when you're walking down the aisle?" Krawcheck says. Unfortunately, there aren't any hard-and-fast rules. But Krawcheck suggests easing into the conversation right from the start. As you're getting to know someone and asking about their family, their hopes for the future, and their career goals, you can also ask about their monetary values. "If you're talking about those hopes and dreams, you're sort of flirting a bit with the idea that you'll be at the other end of those hopes and dreams," she says. And if you're picturing a future together , that's a great time to say something like, "Hey, I'm up to my eyeballs in student loan debt," or "I'm really insecure about money because I grew up without any." (It's also a great time to say, "FYI, my family owns half of Singapore.")