Into the wild by jon krakauer

Jan Burres has a similar dynamic to her as Chris. Jan is a middle-aged rubber tramp (travels by car) who travels around the West selling knick-knacks at flea markets. She meets McCandless when she picks him up hitchhiking. They become close and Jan worries about Chris and his trip to Alaska. She tries to give him supplies like long underwear but Chris refuses to take them.