You don’t have to get into the deepest level of detail on the first date, but when it gets serious enough that you’re considering a long-term future, you can make it less awkward by prefacing your questions with statements that don’t feel judgmental.
Here are some questions you can use to open up the conversation with a more positive spin:
- Are you saving up for anything special? Why is that important to you?
- What’s your favorite thing to spend money on? What don’t you like to spend money on?
- What did your family teach you about money?
- Do you invest? Why do you like investing in that?
- I sometimes worry about money. Is there anything in your money that worries you?
- Debt can be really hard to deal with. What do you think about debt?
