Ashley gets catcalled and wolf whistled at while entering Target and feels a little apprehensive, but also feels a little pleased. Jay asks if her mixed feelings are unique to transwomen or if they’re common among all women.
They discuss the men’s clothes Ashley has already given away and the few masculine outfits she’s keeping for the time being. Jay asks Ashley about changing her watch style and whether she’s considered other accessories like toe rings, earrings, and other piercings.
Ashley fills Jay in on the latest updates to the Standards of Care, a set of guidelines outlining care and prerequisites for care for transgender persons. They talk over the positive and negative aspects of the updated guidelines, including fewer arduous waiting periods for some surgeries trans men may have, and the leftover stagnation among some of the preconditions for surgeries such as SRS.
Ashley shows off a top coat from China Glaze that can give any polish a matte finish and she offers a follow-up about her gel nails and the process she used to eventually remove her gel nail polish.
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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.
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