This week's episode begins with Liza in her kitchen texting Josh. She agrees to go on a date with him and becomes instantly terrified that he might see her naked.
She disrobes and asks Maggie, everyone's dream bestie, to give her honest opinion of Liza's naked body. Maggie compliments Liza's landing strip, but Liza still freaks out because Josh stares at skin all day at his job as a tattoo artist... “Taut, young skin!”
Diana gets a new purse shipped to her and gushes about it with Liza. She pulls a professional camera out of her drawer and asks Liza to take pictures of her and use some filters so she can have a brand new dating profile pic.
Liza and Maggie go to Liza's old house, where her ex-husband David is having all of their belongings loaded into a moving truck. After seeing he has upset Liza, David tells her she can keep it all. He also asks her if she's had something done, referring possibly to her highlights, when Maggie explains, “She just dropped 180 pounds of dead weight!”
A tenured professor liked Diana's profile, prompting Diana to ask Liza to chat with him for her. Using Shakespearian references and rhyme, she woos him into asking Diana for a date, which she eagerly accepts.
Kelsey, eager to sign the Swedish author, goes to one of his readings when she realizes... she doesn’t speak Swedish! She sits uncomfortably and waits patiently to meet him afterward.
Josh (according to Kelsey, “is, like, disturbingly hot!”) and Liza go on their date at a bar, where he runs into a client. She shows off her tattoo on her upper thigh when her friend comes over to talk about getting a tattoo on her lower abdomen, reaching into her pants. Liza becomes increasingly uncomfortable and offers to leave. Josh assures her that all he wants to work is on is her “hot, little... *whisper*”, that leads to Liza's slack-jawed mouth drop.
Kelsey meets the author, telling him of his genius. He asks her to go someplace less crowded, so they go to a bar. Talking about how Kelsey interprets the book, she flat-out asks to sign the author. He says he doesn't want to rush into things... perhaps a bit too intimately. Just when the audience wonders his intentions, he and Kelsey's phones ring with their significant others.
Meanwhile, Liza and Josh enter his apartment making out, and he takes off his shirt. She giggles like a middle schooler and immediately runs to the bathroom to take a Xanax, as prescribed by Maggie. Of course, she takes too many.
Diana goes to meet her professor date; he turns out to be a YouTube vlogger who only asked her out because he loves her purse. He wants to review her bag and flatters Diana, leading her to not believe him. He tells her how he admires her and says that she is a wonderful, successful person and probably isn't called “Little Miss Bag Fag” like he is. She happily helps him take pictures with the purse.
Josh and Liza listen to old records. Liza asks when the album came out, to which Josh replies 1981. She talks about how she wasn't even born yet, to which he replies, “What?” WHAT?! Does he know?! Either way, she passes out on the floor from all the pills and he covers her with a blanket.
Liza regrets passing out on Josh and tells Maggie everything. She immediately crouches down to give Frieda (Liza's vag) a pep talk. The girls begin to sell all of Liza and David's old things in Brooklyn when she gets a text from Josh. Maggie tells Liza she'll take over the sale because, “Frieda deserves this.”
Liza pep talks herself on the way to see Josh, rehearsing how she's going to tell him the truth. “Cameron Diaz is 40. She's not gross, right?” He opens his door and she begins to tell him. He kisses her neck and quickly progresses to her stomach.