‘Fleishman Is In Trouble’ Ending, Explained: What Happens To Toby, Rachel, And Libby In The End?

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A fresh and detailed work on human emotions, ways of dealing with acute problems, and what might be called a severe midlife crisis comes to an end with “Fleishman is in Trouble” Episode 8. Centering around Toby Fleishman, who was still very surprised and unaccustomed to the fact that his marriage of fifteen years with the love of his life, Rachel, was now over, the series focused on the man for most parts. Toby went through a series of feelings, realizations, and acceptances through his journey of being a single father raising two young children without their mother by his side. But Episode 7 had entirely been shown through Rachel’s perspective, making it clear that her struggles with her marriage were just as bad as Toby’s, if not worse. At times, it even felt like the two were not meant to be together at all, and yet the show does not focus on such things at the end. Along with Toby, his best friend and narrator of this story, Libby Epstein had also been going through a rough time in her own marriage, and that too is resolved by the end of “Fleishman is in Trouble.”

Major Spoilers Ahead


Story So Far

“Fleishman is in Trouble” began with the protagonist Toby Fleishman waking up one morning, struggling to accept the fact that his long marriage of fifteen years with Rachel was now over. Despite all his trials of putting himself up on the dating market via apps, he is unable to keep himself distracted from this huge and sudden void in his life. His situation worsened when he found out that Rachel, who had won custody of their two children, Hanna and Solly, had left the kids at his apartment unannounced on a particular morning. It was only through voice messages left on his phone that Toby learned that Rachel had gone off to a yoga retreat earlier than scheduled and left the kids behind. 

The worst fears of Toby come true when Rachel does not respond to his calls or texts, and he gradually realizes that his ex-wife has completely abandoned him and their kids. The protagonist, an established doctor by profession, spends the rest of the summer dealing with every usual but profound problem that one faces both in the roles of a parent and an individual. He finds out that Rachel was probably having an affair with a rich acquaintance of theirs, Sam Rothberg, and is infuriated by this whole situation. He tried several ways to try and accept the fact that Rachel is completely gone, many of which fail, until these realizations gradually start to fall into place. He also has to deal with the growing problems of his children, as Solly is approaching puberty, and Hanna has to face a horrible, unwanted situation at her summer camp. It is over time that Toby starts to see himself as a single father providing love and company to his two children and is happy for a brief time. But certain situations at his workplace bring back his frustration. A patient having to go through a liver transplant at his hospital had developed rare complications after the surgery, and Toby was also denied a well-deserved promotion because he had been irregular at work following his divorce.

During the summer, Toby reconnected with his two best friends from college, Libby, and Seth, with whom he had lost touch following his marriage. It is with Libby and Seth that he spends time sharing his thoughts and feelings, and the friends help him out in many ways. But the three also have an argument as they point out each other’s faults, following which they do not meet for some time. “Fleishman is in Trouble,” also makes us privy to the lives of the two friends. Libby happens to be the narrator of this whole story who had been stuck in the role of a housewife and mother for two years after having worked as a writer in a men’s magazine for years and had been lost in her thoughts ever since then. Even though she had taken the decision to take a break from work, she realized that she was not meant for such a life, and in the process, she had been pushing herself away from her family. On the other hand, Seth, who had always been a proud bachelor, was now yearning to start his own family and was preparing to propose to his girlfriend, Vanessa. It was Libby who, during one of her own self-assessments at Central Park, saw Rachel Fleishman at one of the benches, looking all lost and disoriented. She approached Rachel and learned that the woman had her own troubles going on.

Rachel had been extremely overworked after having opened her own talent agency for actors, and most of her life decisions were missed or misunderstood by Toby. While Rachel yearned and strived for positive changes in her life, Toby seemed to be one to detest it. Gradually over the years, the couple fell out of love, and Toby’s insistence that their marriage was not working led to the couple’s divorce. Even after this separation, Toby refused to understand Rachel, and the woman was all the more overworked. She did have an affair with Sam Rothberg and had gone away to the yoga retreat with him, but this worked out terribly as Sam was only taking advantage of her. Rachel broke down completely following this and returned to her apartment to stay holed up in it for weeks. She did not even realize how time had passed. She took sleeping pills which added to her already messed up situation.


What Happens in Episode 8 Of ‘Fleishman is in Trouble’?

Right after the events of the previous episode, Libby left Rachel sleeping, with a doctor’s appointment booked for her the next day. She knew it was time to let Toby know all of it, and for this, she rushed to her friend’s apartment since his phone was off. Late in the evening, Libby reaches Toby’s apartment and tells him everything she has heard from the woman. Rachel had gone through a horrible nervous breakdown that had left her devastated, with no memory of the entire days and weeks in between. Libby was expecting Toby to have a very sympathetic and worried reaction, but the man does not express anything like that. Instead, he is perhaps more angered by the fact that Rachel confirmed her affair with Sam Rothberg. Toby argues that he too, had gone through severe mental breakdowns and similar struggles but had been able to pull through it all. By now, it is almost evident that Toby does not entirely understand Rachel’s struggles, and this is less of a fault in him than a shortcoming. Libby, on the other hand, could relate more to Rachel in this regard, as she herself was having similar thoughts. She knew it was very possible that she might someday go down the same path, and she tried to defend Rachel because of this. This results in an argument between the two friends once again, leading to Toby asking to be left alone.

In the days that follow, Toby has more realizations about himself and feels bad for some of the interactions with people around him. Most obvious in this list is the argument he had with the infuriated husband of the patient, who had developed even worse complications after her liver transplant. With the woman now having lost her life, the husband breaks down in front of Toby, and the doctor feels guilty for having expected a man who had lost the love of his life to react in a composed manner. Sometime later, Hanna gets ready for her Bat Mitzvah ritual and seems excited at first. Toby takes Hanna and Solly to the synagogue and meets with the rabbi, but while discussing the ritual and especially after hearing all the responsibilities she would have as an adult Jew, Hanna decides otherwise. She tells the rabbi and her father that she does not want to go through the ritual. When Toby wants to know more, Hanna admits that she feels confused and unclear about religion and religious duties. As this is a clear indication of the maturing thoughts and conflicts inside the teenager’s mind, Toby supports Hanna’s wish and comforts her. He then holds Hanna on the altar and informally blesses her into religious adulthood. When the three leave the synagogue, the Fleishmans are a family once again, and they visit the Museum of Natural History. Here, they step into the Vantablack exhibit room again to finally face the void together as a family and a unit, overcoming all their previous fears.

After this, Libby takes us into her summer as she finally feels it important to directly address her own troubles and issues. After having stayed out of work for a couple of years now, she met with an old friend who told her that she was getting a divorce. She had heard of couples divorcing too many times around her, and the whole idea of it, meaning one could start afresh, did enter her mind. Lizzy even got back in touch with her high school romance, possibly to get an out from her mundane life, but this did not work out as she had planned, for the man considered this communication to be only sexual. It was around this time that Libby got a call from her best friend from college, the one who knew her most closely—Toby Fleishman. Since then, the events of the entire summer have been presented before us as they happened. When she met Rachel at the park and then went to report it to Toby, Libby returned home tired and worried at the fact that she had abandoned her own family amidst all this. She was returning home after almost two straight days, and the disappointment was very clear in Adam’s behavior. The next morning onward, Libby tries to get back to being normal with her husband and kids, making breakfast for them. But she realizes that the three she had abandoned for these days have learned to somewhat live without her. She keeps struggling to get close to them, but Adam prevents that from happening, possibly because he fears she will leave again sometime soon. The two have a confrontation during a friend’s party, and Libby admits that she is struggling to figure things out. The woman also finds out that the writer and columnist she used to look up to and admire during her professional days, Archer Sylvan, has died. 

Soon after this, Seth invites Libby and Adam to an important party, which Adam refuses to go to, and only Libby turns up. Toby has also been invited, and together they realize that Seth will be proposing to his girlfriend Vanessa at this party. Despite both their warnings and statements about how marriage was really not a thing to casually step into and that it really does not turn out as happy and prosperous as it seems, Seth decided to give it a try for himself. Toby and Libby now support their best friend’s decision, and they apologize to each other for not being there for each other enough. Vanessa accepts the proposal, and the place bursts into celebration. Toby and Libby still hold their corner, and Libby now tells her best friend that she intends to write a book on the events of his life during that summer. With keen interest, Toby asks how the ending to such a story would be, and Libby responds that on a rainy night: the estranged lover will return, beyond which she could not imagine and would end her book here. The two friends share an emotional moment before both of them leave the party and return to their individual homes.


‘Fleishman is in Trouble’ Ending Explained: Does Rachel Really Return To Toby At The End?

By the end of “Fleishman is in Trouble,” the show beautifully makes itself not just about Toby but about Libby as well. It is almost like Libby is the representative of whatever might have been going on with Rachel; except she is on better terms with Toby. When she tells what her new book is going to be about and talks of an unnamed woman leaving her husband with her kids, the story seems very close to what Libby might someday do to Adam. The woman has been struggling for a long time now to deal with her aging and the fact that many possibilities of life were slipping away from her grasp with every passing day. On her way home from Seth’s engagement party, and also due to the many realizations that she herself had over the summer, Libby realizes that her main problem was this inability to deal with this passing time and growing years. Stemmed by this, she had started to push away her partner and lover for years, as is perhaps natural to do, in an attempt to change something and get back to one’s former time. Unfortunately, this does not work in reality, and Libby, too, has now understood this, realizing that she has only been selfishly pushing her husband and kids away. It did not help her situation in any way but instead worsened her marriage and added more troubles. At present, Libby has a calm acceptance of her age and life and returns home to join Adam in their bed. She holds him dearly and apologizes for being late, but this apology is more for her absence all this time. Adam seems to accept her apology and tells Libby that it is fine since she always returns, no matter how late. Adam still looks open and accepting. While it does not mean that all of Libby’s problems and struggles with her familial life would suddenly end after this, such a soft reconciliation is very positive for the couple, as it indicates that they are perhaps ready to give themselves one more chance.

At Seth’s party and over the summer, Toby realized how he had kept himself away from his friends for so long, and he now truly wants to make up with them. With Libby, he does perhaps the best he could have done by telling her that he truly still sees her with all the potential and brilliance that he saw in her during their college years. To him, he said, Libby was no different from her younger self, and this greatly helped her towards the right way. After she has a sudden wish to return home and apologize to Adam, she texts Toby about this, and he, too, leaves the party. On his way back home, thunder and rain crashed down from the skies, ending the heat wave Manhattan had been facing all that summer. In a similar fashion, Toby’s fears, negative thoughts, and frustrations also wash away as he is filled with new hope for life and survival. After all, this was indeed a new beginning for him that probably many would yearn for. It is not something that he had wanted, but Toby now truly believes that he has to live through it and, more importantly, help his kids through it. He decides to look for a new apartment, and looking out the window, he takes a moment to consider the vastness and sheer hopefulness of human life. He realizes that as much as one could crib and complain about life, there are equal amounts of hope and potential at every time, too. Just at this moment, he hears a key being turned on the padlock of his apartment door, and as the door opens, Rachel Fleishman seems to have returned home. Whether this is the reality or whether it is the hopeful imagination of Toby is left unclear as “Fleishman is in Trouble” cuts to its end here.

While “Fleishman is in Trouble” begins with layers of complicated struggles following the end of one’s long years of love, the end is filled with hope and life to the brim. The series did have the feeling that it would be therapeutic in some senses, but the way this has been executed perhaps makes it a really remarkable drama series in recent months. Whether Rachel really returns to Toby and her children or not, Toby knows his, and his kids’ lives will go on as usual. What such an ending affirms is perhaps that even if this return is imaginary, the next time Toby and Rachel would meet, they would at least understand and respect each other more than they had in recent times. Beyond seeing each other as opponents in a divorce case, they would acknowledge each other as two struggling fellow human beings who were once inseparably in love. While this would not ascertain that the couple would get back together, it would ensure that the children would be helped by the situation. Like the show tries to present, sometimes the best thing in life is perhaps to avoid the worst; there are plenty more things to be hopeful about and look forward to in life.


“Fleishman is in Trouble” is a 2022 Family Drama series streaming on Hulu.

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Sourya Sur Roy
Sourya Sur Roy
Sourya keeps an avid interest in all sorts of films, history, sports, videogames and everything related to New Media. Holding a Master of Arts degree in Film Studies, he is currently working as a teacher of Film Studies at a private school and also remotely as a Research Assistant and Translator on a postdoctoral project at UdK Berlin.

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