Pay Dirt Photo illustration by Slate. Photo by Digital Vision/Getty Images Plus.  Our advice columnists have heard it all over the years—so we’re diving into the Pay Dirt archives to share classic letters with our readers.  Submit your own questions about money here . (It’s anonymous!)  Dear Pay Dirt, My daughter “Isabella” is married to a successful young lawyer and is eight months pregnant with their first child. My first wife and I wanted more children, but it never happened. She lost her battle with cancer when Isabella was 16. I didn’t feel like dating again for almost five years. Over the next few years I saw several women, none very seriously. Then, at Isabella’s wedding in 2019, I connected with one of her bridesmaids, “Madison,” a lovely young woman I’d last seen as a gawky teenager. Isabella was shocked when she found out Madison and I were dating, but didn’t expect it to last long. But I just proposed to Madison, and she accepted. I took Isabella out to lunch to tell her.…