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 one might avoid banging one's nails into objects.