December 31st, 2011
Jay figures it’s time to ask Ashley about sex and romance as a trans woman, asking her about underwear preferences, whether she ever finds panties arousing, and the added complexities of a trans woman dating lesbians. For instance, would Ashley tell someone she’s dating about her trans status before they have sex?
Jay wonders whether testosterone blockers affect erections and if that has any negative effect on sexual intercourse. Ashley doesn’t rule out being attracted to trans women and cisgender women alike, and for the first time, starts seeing herself as a bisexual-leaning lesbian.
Jay asks Ashley how she approaches modesty regarding her breasts, such as while wearing her new swimsuit for the first time or in the changing room with friends, and whether she feels self-conscious around other areas of her body.
Ashley has some elevator chitchat with her manager but later realizes he may have been unaware of the subtext she was trying to convey. She also rethinks which clothes she might bring while visiting her family over Thanksgiving and describes her occasional but conspicuous chocolate cravings.
Ashley shows off her pearlescent white and pink nail polishes from Essie (Oui Madame and Pink Diamond) and asks Jay and the audience for ideas on how she can avoid banging her nails into objects.
December 15th, 2011
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.
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 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.
October 18th, 2011
Ashley explains how she prepared to come out to her boss, with some help from the Human Rights Campaign, and her conversation with the boss to start the process around her transition at work.
Ashley also ponders an upcoming visit from her parents and mulls over ideas on how she might ask them to call her Ashley.
Finally, Jay and Ashley talk about makeup removal and cleaning makeup brushes.
October 5th, 2011
Ashley talks with Jay about how she keeps her boobs under wraps at work and why she hasn’t come out to her boss just yet.
Ashley also educates Jay about some potential surgical options including facial feminization surgery (FFS) and sexual reassignment surgery (SRS). And she offers some tips on spacing one’s polish coats to prevent chipping.