"Rebecca wants to go to jail, you want to get a disorder — this is like a really messed up episode of "Sex and the City."
— Heather to Josh
Rebecca voluntarily goes to jail, Nathaniel goes on a survivalist excursion to get over Rebecca, and Josh tries to self-diagnose.
Songs
"What's Your Story?" (sung by Rachel Bloom, Karibel Rodriguez, Kalea Mcneill, Pam Murphy and Jully Lee)
- Affectionate Parody: Of "Cell Block Tango" from Chicago. Rebecca tries to do something similar to that song by singing and dancing around chairs and getting the other Girls Behind Bars to share their stories, but it doesn't work.
- Prisoner Performance: Rebecca goes to prison and organizes a theater class for her fellow prisoners. She's the only one who's really into it, and cares more about her class than getting out of jail. She tries to craft an original performance based on her fellow prisoners' stories a la Chicago, but everybody else's reason for being in jail is incredibly sad.
- Wrong Genre Savvy: Rebecca keeps expecting her fellow inmates to be badass rebels spitting in the face of an oppressive system. Instead, each one's story is a demoralising account of flawed people, petty injustice and just plain rotten luck.
"No One Else Is Singing My Song" (sung by Rachel Bloom, Vincent Rodriguez III, Scott Michael Foster and cast)
- Distant Duet: Distant Terzet, to be more specific. In the first part, Rebecca is singing from county jail, Nathaniel is singing from the forest, and Josh is singing from Home Base. And then they invoke Massive Multiplayer Ensemble Number.
- Massive Multiplayer Ensemble Number: Rebecca, Josh, and Nathaniel say that calling on the company would be impossible...and then it happens.Rebecca, Josh, and Nathaniel: How beautiful would it be
Nathaniel: If it was the entire company
Josh: But that's impossible...
Darryl: Impossible...
Paula: Impossible...
Heather and Valencia: Impossible
Hector: Impossible...
Grocery Clerk With Half an Eyelid: Or is it? - Informed Loner: Parodied. Rebecca, Josh and Nathaniel are all singing about how nobody else is singing the same song as them and how lonely and unique they each are, and pretty soon they're joined by the entire cast all singing the same thing.
- Medium Awareness: At the end, Nathaniel and Josh seem aware of the other cast members and wave to them from their "boxes". Rebecca, however, continues to think she's alone.
- You Are Not Alone: The message of the song, albeit with the snarky rider of "... and you'd realise that if you'd just get over yourself."
Tropes
- Acting Unnatural: Rebecca's friends listen in on her conversation with Nathaniel and when it ends return to awkwardly standing around the kitchen. Darryl starts pretending to eat ceviche.
- Brick Joke: Near the beginning, Rebecca explains that people usually say they "went to school in Boston" instead of straight up saying "Harvard". At the end, when Paula goads Trent into waking up by implying he went to Princeton, he corrects her by saying that actually, he went to school in Boston.
- Girls Behind Bars: Rebecca's in county jail and tries to interact with the other inmates, even attempting a fanservicey "Cell Block Tango"-like number.
- Happy Ending Override: The Judge won't accept Rebecca's guilty plead from the previous season's finale because it was basically not one. Rebecca spoke to Paula, not the judge, about a number of things she wasn't on trial about, in what was more of a speech than anything else. Something of an unusual instance of this as it involves things becoming better for the lead rather than worse.
- Hollywood Psych: In-Universe. Josh is sure that he has some kind of mental disorder, but as everyone keeps telling him, he's just kind of dim and oblivious.
- Macho Disaster Expedition: Nathaniel goes on a brutal survivalist trip, but gives up pretty quickly when it's pointed out that it's just an unhealthy way of coping.
- Madness Mantra: Rebecca spends what seems to be several days repeating "I deserve this" to herself.
- Strange Minds Think Alike: Both Hector and the therapist Josh sees complain about online quizzes getting their Sex and the City character wrong.
