Jay asks Ashley if she had considered wearing a wig until her hair had grown out to a length that she felt was more feminine. Ashley answers a question from a viewer about her views on men wearing women's clothing as she was growing up, including performers like Eddie Izzard and comedy troupes like The Kids in the Hall and Saturday Night Live. Jay also checks in with Ashley whether her early explorations with women's clothes had any erotic subtexts.
They also chat about shopping for clothes, from her interactions with salespeople to arbitrary clothing sizes and the chicken-and-egg problem she faced as she was kicking off her transition.
Ashley tells the story of her first trip to any ladies' room (hint: it was at work, sort of) as well as the sense of belonging she felt when she first went to a crowded one.
Ashley offers a tip on retaining supple skin under the eyes and talks through an idea that might help reduce the chances of chipping her nails while fishing through her purse for her keys. Lastly, Ashley shares a short time-lapse video montage of self portraits she had taken over the past few months using the "Everyday" iPhone app.