Scarlett O'Hara and Melanie from Gone With The Wind, just to have a front row seat to their dynamic. If Melanie did know that Scarlett loved Ashley, it would add extravagant depth to the conversation. I'd simply ask how does one know they are loved and then sit back awhile and listen. The holidays tend to bring fresh blood to old wounds. Perfect timing.
Offred The Handmaids Tale. I greatly enjoy conversations regarding the past, current and future impact of feminism. I would ask endless questions about her world.