I'm thinking of a (fun, borderline-historic) question about items that Margaret Thatcher might have carried in her (somewhat) often-cited handbag:
A quote by Abraham Lincoln, on at least one occasion a book by Friedrich Hayek, that much we know. A conventional upper-middle-class woman's usual items, that much can be assumed. Was she a smoker, did she need to carry a pepper spray? Was there a clunky pre-mobile-phone emergency communication device? What else?
Now do you see potential in a question of this type, or is it hopelessly open-ended and perhaps all too trivial?