Ashley has waited for months for her parents to start using the name Ashley instead of her birth name, but they won’t, so she tries to explain her request again in a carefully worded letter. Unfortunately, the letter doesn’t go over well and her parents tell Ashley that she’s hurting them by not considering their point of view.
Ashley’s parents are visiting in a few weeks and she’d love to try a new restaurant with them, but she worries that her parents would out her as soon as they started making small talk with the restaurant staff.
Despite this, Ashley has started the process of legally changing her name, and she tells Jay about all the paperwork, filing fees, and her eventual appearance before a judge, who could potentially decide not to grant her request.
Jay also learns how to get the most out of Too Faced Shadow Insurance eyeshadow primer and a tip on cleaning the lint from one’s dryer screen without scuffing one’s nails.
(Ashley’s polish in this episode is Aruba Blue from Essie. We aren’t being paid to say this — just thought maybe you’d like to know.)
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Ashley answers 7 Questions for the we happy trans project, such as who’s been most supportive of her transition, changes she’d like to see in the world, and how she’s helping to make those changes.
Jay asks how Ashley’s new coworkers are accepting of her gender identity, given that some knew her since before her transition while others have only ever known her as Ashley.
Ashley receives a postcard from her vacationing parents, but they addressed it to her birth name and Ashley can’t bring herself to read it. She wants to talk with them again about calling her Ashley, but worries that her parents could become fatigued on the subject if she were to bring it up too frequently. She and Jay also discuss the unusual evidence her mother cites to try to refute Ashley’s gender identity.
Jay learns that Too Faced Shadow Insurance (an eyeshadow primer) benefits from a little shakey-shake before use, as one would do with a squeeze bottle of ketchup (or with natural peanut butter if you’re fancy). Ashley also discerns that her technique for repainting some nails (but not others) with a zip-top bag requires a new baggie about every six months.
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Ashley is frustrated by her parents’ lack of acceptance, and suggests that instead of emphasizing her new happiness to them, she could instead explain how bad she’d feel if she had to return to her life before transition. And if they don’t come around and she tries to bring this up with them, should she try to broach this over the phone or might she have better luck with a letter in the mail?
Jay and Ashley chat about the group sessions organized by her gender therapist that she attends with several other trans women. It’s a cozy supportive environment where they talk about some of the progress the other women in the group have made with their transitions and various ups and downs.
Ashley talks about some of the trans community she’s come across online including the alternating-weeks #transchat and #queerchat each Sunday. Jay asks whether Ashley has come across much cyberbullying and Ashley talks about some of the microaggressions she’s come across in passing.
Ashley offers a follow-up on two makeup products discussed on earlier episodes. Oh, and they veer into talking about nail polish too. Yeah, like that ever happens.
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Ashley teaches Jay about the nuances and changing meanings of some of the more hurtful slurs directed toward trans folks, with help from GLAAD’s transgender glossary of terms.
Jay asks Ashley to elaborate on what she means when she says she’s “always been a woman” and if that means she regrets not having come out at an earlier point in her life.
Together, they discuss whether it would be feasible to raise a baby as gender neutral until they were old enough to express their gender identity.
They also discuss the nail-protecting power of gloves and Ashley sings a jingle about them. (Caveat: The “gloves song”—all three seconds of it—is only available in the video version of this episode.)
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Ashley’s father seems to view her gender therapist as a sort of puppet-master (puppet-mistress?) pulling Ashley’s strings, even though Ashley switched from individual counseling to group support. Ashley’s parents say that they accept what she’s doing, but they make a point of telling her they don’t condone it. Jay thinks it means they now understand it’s not a phase, but Ashley infers it’s more likely that they think she’s crossdressing.
Ashley wonders how to get through to her parents and is nearly ready to give up, especially after her dad says that he doesn’t entirely accept publications like the DSM (Diagnostic and Statistical Manual) as truth. Ashley also continues to long for any recognition of her femininity from her mom.
Jay and Ashley discuss some fun things as well: her new pierced ears, the ideal diameter for hoop earrings (1.68 inches), using a flatiron, and matching polish precisely by bringing specific clothes to the store. Ashley finishes by describing some nail polish shortcuts and their inherent tradeoffs.
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Ashley visits with family and friends during the yuletide season and her parents obstinately use the wrong name and pronouns for her, creating confusion among some guests. For Ashley, it’s like insisting on using a woman’s married name even after she split with an abusive husband.
During her visit, Ashley’s dad conspicuously mentions that it’s okay if she doesn’t attend mass with the family on Christmas, which makes Ashley wonder if her dad is telegraphing some embarrassment to be seen with her at church. While making sandwiches, her mom lobs Ashley a verbal punch in the gut, seemingly unaware of the weight behind her words.
Ashley tries to remain optimistic her parents will eventually come around but it’s hard to imagine what will lead them toward full support. Ashley’s already feeling anxious about her parents’ upcoming visit in the fall. However, they are surprisingly understanding when Ashley talks to them about her recent layoff.
Jay learns that concealer can be a stand-in for eyeshadow primer in a pinch, and Ashley shows off a nail protein base coat by Nailtiques. Jay also learns what Ashley means when she describes herself as being “thirteen in girl years”.
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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.
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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.)
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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.
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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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