Q: “I am a 58-year-old widowed male, in good physical and financial shape. I have no debts, own my home outright and recently retired with a pension. My daughter has forewarned me that dating is not like it was 40 years ago. How do I protect myself if I connect with a lady and the relationship goes south?
—Joe Lidster, Kamloops, B.C.
A: Your daughter is right: Dating in the era of Tinder and eHarmony is very different from your first go round. And you’re different too: financially established, in retirement and, by the sounds of it, a very good catch. So you’re right to date with some caution. The key is to understand each other’s values around money. You don’t need to talk about specific numbers but you do want to get a sense of how this person likes to spend and save. Setting clear expectations about who pays for what is a good exercise in communication that will either further solidify your bond, or bring you closer to breaking up. Eventually, you should go through the big stuff like net worth and cash flow—as an outstanding divorce settlement, no retirement savings or high credit card debt may or may not be a deal-breaker. But take note: Don’t move in together until you are totally comfortable about the finances because that step muddies the legal picture.
Bruce Sellery is a frequent guest on financial television shows and author of Moolala. Do you have your own personal finance question? Write to us at firstname.lastname@example.org