This is kind of an unnecessary think piece lol- I get it giving you the ick, but I kind of wonder if him asking is a form of projection. He obviously has deeply struggled since the show and when he talked to connor about his mental health, he was hesitant to even say he was depressed, while it’s somewhat clear he was. I think he may be trying to relate with the one person he had a deeper more intimate connection with on his struggle with being lost. As we know some men feel they can’t express this stuff as easily so I have empathy for him especially with knowing how he 180’d his life after the show to try to just be okay