Fleishman is in Trouble (Episode 3): Recap & Ending, Explained

Fleishman is in Trouble Episode 3

Fleishman is in Trouble (Episode 3): Starring Jesse Eisenberg in the central role of Toby Fleishman, ‘Fleishman is in Trouble’ presented a darkly humorous narrative through its first two episodes. While Toby is 41 and recently divorced, we do not get to see his wife, Rachel (played by Claire Danes) besides a few glimpses of their arguments from the past. Instead, we witness his close relationship with his college friends – Libby and Seth, who help him cope with the loss of marriage, in their own ways. Created by Taffy Brodesser-Akner, it dives deeper into the factors that caused the relationship between Toby and Rachel to eventually break.




Fleishman is in Trouble Episode 3 Recap

Episode 3: Free Pass

Directed by Jonathan Dayton and Valerie Faris, the third episode titled ‘Free Pass’ takes us down memory lane of Toby’s (Jesse Eisenberg) past. At the end of the previous episode, we see Toby learning about Rachel (Claire Danes) being present in the city unlike what she kept telling him. She was sleeping in a park, and by the way, her mom-friends mention her condition, she does not seem to be in a sound state. Still, Toby is conflicted with the thoughts of how it affects him in particular. He ruminates over the root of the drift in their relationship over the years. We encounter the events from their past right from the moment when the drift started to occur – the moment of their meeting.

Fleishman is in Trouble Episode 3

It was a college party where Toby had gone along with Libby (Lizzy Caplan) and Seth (Adam Brody). Seth was a womanizer since this age and was flirting with one of the girls. Toby and Libby were looking at his efforts from a distance and making fun of him in their in-synch style of humor. It feels odd while looking at their chemistry that they were not romantically involved with each other. Libby, talking through the voiceover, explains why. It was her weirdness about relationships and his sense of himself as unlucky in the romantic arts. Seth interrupts their conversation while telling them his plans with the same girl.




During the same night, Toby stumbled upon young Rachel, sitting by herself near the drinks counter. He tried making a conversation by offering the terrible punch made at the party while having spat it out before. They have a laugh about the same and it becomes an ice-breaker for him. Rachel was proud at the time of being a great negotiator and although ambitious, she was yet to discover her niche. In their following dialogue, Toby fell over for her and they ended up spending the night together. In the following days and weeks, they grew fond of each other. Toby reveled in the joy of finding his soulmate in her.

Their romance is shown through rose-tinted glasses, similar to the classic romantic comedies, perhaps owing to it being Toby’s vision of reality. He eventually proposed to her after a gushy meeting, and she agrees. However, by then, he had considered her compatible side (with him) to be the only side of her personality. Rachel’s inclination towards rising up the ladders occasionally seeped in through their conversations. But Toby was too awestruck by the existence of the relationship itself to notice this conflicting worldview with his. And meanwhile, as she hoped, she kept making progress and getting one promotion after the other.




On one particular night, Rachel discovers an underground artist named Alejandra Lopez who soon became a celebrity due to her support and her theatre agency’s backing. Toby was enamored by her skill to know perfectly well what people want and bring it to them. However, the rise in her level of position resulted in her getting busier to the point he could not attend to the things he loved. At a party, which he was planning to enjoy with Seth, Libby, and her, she shared an urgent plan at the last moment and leaves him with no choice but to tag along. Libby recounts it as one of the encounters where he started losing control over his life.

On one rainy night, she came home soaked wet, disheartened for not getting the promotion. She sensed it as being punished for not being okay with sleeping with a man from the middle-management of their company. While she was shaken by the incident itself, he kept her feelings aside and starts contemplating how it affects him. He was at the party where the dialogue occurred, and he had no idea about it. Soon after, she got pregnant with his child and on the day of the childbirth, her assigned doctor is absent without notice.




The replacement doctor tried to push the kid’s membrane and make the water break by force. It happened right when Toby was not in the hospital room she is in, and she keeps reminding him about his inability to use his position to help her in that situation. Even the thought of using influence might have irritated him. After this traumatizing incident, the sadness enveloped them to the point where it felt like they forgot how to smile. This realization made her take a sudden decision to leave her current agency and start a new one on her own.

That’s when she started Fleishman and Co. and hired employees from her previous organization. This new development made her feel in control of herself but left him with added responsibilities since she got busy with hers. Their contrasting worldviews became evident in the following time. He was interested in providing service to people and fulfilling his noble responsibility as a doctor. Unlike her, he did not wish to be a part of the affluent to feel validated. Her seeking of these affluents, however, was more to use networking as a way to enter their world and to better her life.




She despised him for taking the moral high ground in their arguments, while all his career plans were led out for him, whereas she had to build them on their own from the scratch. Unlike his well-to-do family, she did not have the same level of financial or emotional support. As a desire to be a part of such affluents, she made him agree to let their kids go to private schools instead of their public ones, even if they are overpriced. She understood the necessity of being a part of these circles, while he felt like he was cheating with his values.

Fleishman is in Trouble Episode 3 Ending, Explained

Over the course of time, the constant disagreements between Toby and Rachel caused their steady relationship to slowly disintegrate to reveal their unflattering sides to one another. When an opportunity came knocking on the door that could provide him with a monetary promotion besides a work of his interest, she did not agree with the idea of moving to Philadelphia. When New York is brimming with talent wanting to be in the theatre, moving to Philadelphia made no sense to her. His plan of shifting failed moments within he mentioned it to her.




It bothered him beyond limits that despite being able to provide what she always expected from him, she persuaded him to reject this attractive offer. She became especially repugnant to him at a gathering with some family friends where she was asked to name a celebrity that she would like to sleep with if given a chance. She mentioned Sam Rothberg – a person she knows instead of an unknown celebrity, as what they expected her to talk about. Then back to the present, he remembers Sam’s name being mentioned during this gathering and locates him online. Only the next episode can reveal what he will do with this piece of information.

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FLEISHMAN IS IN TROUBLE EPISODE 3 LINKS: IMDB, WIKIPEDIA
FLEISHMAN IS IN TROUBLE EPISODE 3 CAST: JESSE EISENBERG, LIZZY CAPLAN, CLAIRE DANES, ADAM BRODY, JOSH RADNOR
Where to watch Fleishman Is in Trouble (2022)
Akash Deshpande

Obsessed, fascinated, and always nerding out about cinema! You can find me in the corner of a room ruminating over the last TV series I watched.