It's Dress Like Wednesday Addams Day at Scarlet and Jane's (Katie Stevens) got a big job to do: Can she recreate the back-breaking sexual position the magazine is trying to pitch readers? The short answer is no, but that's the least of her worries. Our girl's yet to experience an orgasm.
That reveal comes (sorry) after she's assigned yet another story she's not in love with. Jacqueline (Melora Hardin) wants a personal essay about Jane's best orgasm, which is tricky seeing as how she's never had one — not even the solo, flipping through Mahershala Ali's GQ shoot in bed kind. Problem-solver Kat (Aisha Dee) wisely suggests a call to her gynecologist to rule out any medical issues.
While Jane struggles to get off, Sutton (Meghann Fahy) is looking to lean in. She corners her boss Lauren (Emily C. Chang) about a potential career advancement. Lauren reacts in a supportive fashion, and agrees to line up some informational interviews that are in line with Sutton's business degree. The catch is that Richard (Sam Page) is the first person she consults, not realizing that he and Sutton are sleeping together.
They're not the only ones mixing business with pleasure. Kat wants Adena — for a follow-up interview, and to maybe reenact one of the sex dreams she's been having. It's been radio silence since the social media director sent her photographer pal that topless selfie, but she's in luck. Adena pops by the office just in time to agree to an interview and invite Kat to her upcoming gallery show.
It's hard to not feel icky when Richard kicks off his informational interview with a Fifty Shades of Grey crack. Sutton's not looking for his advice, but eventually comes clean about her career goals. Her mother's financial irresponsibility has given her a practical outlook, and obtaining a higher-paying position is her top priority. Richard recommends an opening in ad sales. Sutton celebrates her potential move out of Valley of the Assistants by grabbing Shake Shack with the supportive Alex (Matt Ward), who is the physical embodiment of boyfriend material and should be snatched up immediately.
Jane, still on her orgasm mission, decides the office elevator is the perfect place to have an intimate cell phone conversation about her private parts. This ends with her screaming "PROBLEM WITH MY VAGINA" at her gynecologist just as the doors open to let in Pinstripe sex columnist Ryan (Dan Jeannotte), who is basically Gerard Butler in every rom-com he's ever made. Writers, why should Jane be listening to Ryan say her writing is "cute" and that he hopes her "vag is okay" when she could be dining with Alex at Shake Shack? Hasn't she been through enough?
Evidently not. Step two in Jane's pursuit of the big O is to consult a sexologist, who advises her to use a Goop-approved yoni egg and to watch porn so she can tap into the right sexual fantasy. The girls gather for some XXX-rated fare, where the only thing that falls flatter than Jane's confession that un-PC Civil War fantasies make her toes curl is Sutton's news about the ad sales job. Kat is particularly harsh, calling the job boring. An offended Sutton storms off to Richard. Kat splits, and Jane fruitlessly contemplates office romance fantasies featuring Ryan. Then she eyeballs that yoni egg.
If you know your Sex and the City, you can guess what happens next. The yoni egg, just like Carrie Bradshaw's diaphragm, gets stuck inside Jane. It falls to Kat to coax it out while Jane lies with her legs akimbo in the fashion closet. The experience has an odd impact; fishing inside her friend's vagina convinces Kat that she's not ready to *go there* with Adena.
But she will go to her art opening, which draws undercover art critic Ryan. It's an eventful evening. Sutton receives a call from Richard telling her the ad sales job is hers. Unfortunately, it's not what she truly wants. She tells Alex that she'd rather pursue a job in fashion, even if it means less pay and more risk. Later, they toast her decision with a bottle of Veuve Clicquot, paid for with the $100 safety money she's been holding on to for years.
Whether or not Kat is sexually attracted to Adena may be a moot point; turns out, she has a girlfriend. Still, Jane — who has just turned in a lackluster article draft that Jacqueline wants revised — is so impressed by her pal's risk-tasking spirit that she decides to shake things up herself. She marches over to Ryan, lays a big smooch on him, then swans out of the party.
Her next big leap: Writing the honest account of her sex life, sans anonymity, that Jacqueline wants. Jane is ready to share her story, which is good, because it seems everyone in the tri-state area has some sort of Google alert for orgasm content. There's no climax, but the episode ends on a high note anyway.
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