I’m not QUITE sure if this is what Thoon is referring to, but should you choose The Wheel of Fortune as the Youthful Naturalist’s fate he retains his humanity even as the Boatman, comes around to quite enjoying his occupation and after an unhappy accident takes you on a little boat ride to tour the other afterlives
Of course, even in The Hanged Man it’s implied you stay in touch. It’s just…implied to be a little more remote given what the Natural has become.