November 30th, 2011
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.
November 21st, 2011
Ashley talks about her parents’ recent visit and how she asked them to consider calling her Ashley rather than her birth name.
She also recounts the reprimand she received from her employer for using the bathrooms matching her gender presentation rather than those of the gender she was assigned at birth. Ashley struggles to grasp her employer’s rationalizations, but she resigns herself to workdays blighted by elevator slogs to restrooms on different floors.
Jay follows up on his earlier suggestion that Ashley buy some “girly glasses” and asks whether HRT has tempted her to drink more so-called “girly drinks” (even though Jay admits there’s no logic to that question). Ashley announces her nail polish bottle count and suggests a way to trade some of her lesser-used polishes in exchange for others she might rather have.
Ashley talks about which polish she finally decided to wear during her parents’ visit, Nite Owl from Orly’s “Birds of a Feather” collection, a taupe with just enough shimmer to keep things interesting. Ashley also espouses the value of the common cotton swab and makes the case for Johnson’s brand over Q-tips for this tiny but essential makeup tool.
November 16th, 2011
Ashley attached her Flip camera-sized camcorder to her shower door (with a Gorillapod flexible tripod) and recorded her makeup routine the morning of her transition at work through the reflection in an adjacent mirror. Then, among the editing process, she adjusted the video to play back at 8x speed so that the sequence could fit within about 5 minutes. She also added educational notes about which product is being applied at each stage as well as a running timer at the bottom of the screen (a timecode).
It so happens the batteries in Ashley’s camera ran out just before she did her lips and hair that morning, so while those bits didn’t make it into the video, you can imagine if you’d like tacking on a handful more minutes toward the end to take care of those.
November 14th, 2011
Ashley celebrates her first week presenting as her gender full-time, with warm words and open arms from her coworkers, a more comfortable wardrobe (as well as a new laptop bag), and some entirely unremarkable bathroom visits. She and Jay also talk about how it’s been different carrying around one’s day-to-day items in a purse rather than a wallet nestled in one’s back pockets (or, in Jay’s case, a messenger bag).
Ashley recounts some early shopping trips with friends soon after she had come out to them and how they had come along with her for a gleeful day of shopping while also playing the role as sort of a fashion tour guide to help Ashley learn the ropes of her new clothing options. She also reminisces about a recent trip to Nordstrom in which they not only had shoes in her size — oodles of them — but also shoe clerks with the attentiveness that made her feel like she had acquired her own shoe sommelier.
As time drew closer to her transition at work, Ashley sprang for a series of makeup lessons from both an independent makeup artist as well as one from her local MAC store. Eager to share some of what she learned, Ashley conveys how one can use a sponge wedge to help smooth one’s foundation and a trick that can make it easier to recover from small mistakes when applying one’s eye makeup.
November 7th, 2011
Ashley’s work finally makes the announcements to her coworkers about her transgender status, albeit with the grace of someone tripping down a flight of stairs, leading to cringes from herself and several of her team members. With euphemism piled atop euphemism, Ashley’s worried if everyone in the company will even be able to unravel the news their management is foundering to convey.
Jay talks with Ashley about her reactions to pet names she might come across — words like ‘darlin’ or ‘cutie’ that one might hear from a store clerk or a server at a restaurant. Jay also asks Ashley which name and pronouns she’d prefer when someone is referring to her in a story from before she came out.
Ashley also teaches Jay about two common types of toe separators one can use when painting one’s toes and weighs the advantages of each. Jay also learns about a new type of polish that allows one to wear two nail colors at the same time in which the second color peeks through a series of cracks in the first.