January 23rd, 2012
Ashley gets laid off, inferring through the business-speak that it was a means for the company to cut costs. She and Jay discuss searching for a new job now that Ashley is presenting as female full-time, but Ashley expresses doubts about whether she can pass during the entirety of an interviewing process—especially during phone interviews—and she forms a plan to deflate the elephant in the room.
Jay asks Ashley to elaborate on her blooming albeit sporadic attraction to men, or more specifically, Ashley’s newfound ability to determine which men are attractive. (No surprise here, but Rob Lowe and Ryan Gosling are on the list.)
They also discuss how Ashley maintains her eyebrows (she was having them waxed even before she came out to herself), whether Ashley ever does her make-up in the car on the way to work, and if she’s considered trying out a totally trashy or promiscuous make-up look, just for fun.
Ashley teaches Jay a trick for bending a mascara brush to make it easier to apply and how one can smudge eyeliner with a cotton swab if one is without a dedicated eyeliner brush. They do not talk about nail polish.
January 16th, 2012
Over Thanksgiving, Ashley’s parents reveal that they still misunderstand her transgender status, claiming that she’s cross-dressing and that she’s making her coworkers uncomfortable. Her parents also wonder if Ashley’s gender therapist is putting ideas in her head, and worry that keeping and finding employment will get harder for Ashley.
Ashley attempts to talk with her dad about some recent MRI studies indicating that transgender status is likely rooted in biology—that transgender people are born that way—but the information is quickly swatted aside by her dad’s cognitive dissonance.
Ashley explains that her favorite top coat, Seche Vite, works best when immediately applied on top of the second coat (before the second coat even starts to dry) and she passes along a technique that you can use to selectively remove nail polish from only a few nails without affecting the rest of your manicure.
(Ashley’s polish in this episode is Wicked from Essie. We aren’t being paid to say this — just thought maybe you’d like to know.)
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 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.
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.