I like this. He becomes a Hugo award winning writer and, in an interview, mentions his high school teacher Mrs. Bisby as his earliest supporter of his writing. Not long after, she hears about the interview, and she shows up at one of his book signings. Afterward they go out for drinks and talk and catch up. Before long they are making reasons to see one another and eventually it happens.
I like an affair where he remembers her and reaches out to her from prison. They become pen pals, and slowly begin writing more explicit letters to each other. Seducing her with his words. She shares g-rated family photos that gets him horny thinking about her.