In response to your first question/comment:

I could see that advice applying to younger people, but folks over 40 are going to have some history.

I’ve probably asked about the most recent serious relationship/when the divorce was final on at least 1/2 my first dates. It’s only been awkward once.

I keep it VERY simple.

Bonnie (at a moment that doesn’t seem awkward): So, when was your last serious relationship? (Or: When was your divorce final?)

Dude: Blah, blah, blah.

Bonnie: Oh, that’s been a long time. (Or: Oh, that was really recent.) (Or: Oh, I’m sorry, but I’m glad that’s behind you now.)

Bonnie: Are you enjoying seeing what’s out there now? Or do you think you’d like something a bit more serious?

Dude: Response

Bonnie (moving onto other subject): Blah, blah, blah.

That’s it. It’s never a long conversation unless the DUDE turns it into something longer.

I keep my tone serious but light. I do not ask 20 questions or make sweeping comments about his exes. And I move on very quickly the majority of the time. It’s pretty painless.