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...the one who had left them for a jerk, and messed up their lives, and was devastated with guilt about it.
Are you going to include any of the Letters? Sometimes, no offense, they've outshone you on a given day.
I'd really try to vary your own responses that you select, and don't let too many of them be the swoozy, furrowed-brow-while-I-free-associate ones. When you think more clearly and narrate with more discipline I find your replies more effective.
The imaginative empathy isn't a bad approach, and sometimes your wandering transports do take you to a line that nails the heart of something, but it's inconsistent. (Maybe with detachment you'll see which times it's worked, and which times you're just indulging.)
Great idea to do a book, Cary. Hope they fly.