Fleishman is in Trouble is a 2022 Dramedy miniseries airing on Hulu (but branded as an FX show), created by Taffy Brodesser-Akner and based on her 2019 novel of the same name. Toby Fleishman (Jesse Eisenberg), an early-40s doctor in the Upper East Side of Manhattan, unexpectedly finds himself a hot prospect on the dating apps after a messy divorce from his wife of 15 years, superstar theatrical agent Rachel (Claire Danes). But his nascent playboy days are disrupted when Rachel drops off their children at his apartment in the middle of the night en route to a yoga retreat. When Rachel fails to pick up the kids afterwards, Toby and his recently-reconnected college friends, aging Casanova Seth (Adam Brody), and Happily Married journalist Libby (Lizzy Caplan) try to determine what Rachel's absence really means.
Fleishman is in Trouble contains examples of:
- Awful Wedded Life: Toby and Rachel's crumbling marriage and subsequent divorce. Obviously.
- Author Avatar: Libby. Like Brodesser-Akner, she is a former writer of celebrity profiles for a men's magazine. (Brodesser-Akner wrote for GQ for many years)
- Bratty Teenage Daughter: Hannah, very much in her annoying teenage years. It is amplified by her desire to fit in with her much richer friends.
- Cast Full of Rich People: the Fleishmans live in a very affluent area of Manhattan and most of their friends are über-wealthy. This is a source of tensions for them. Rachel craves acceptance and inclusion in those überwealthy circles and she ends up pressuring Toby into having a better-paid job (despite him being a well-paid medical doctor that loves his job). Toby despises their shallowness and vanity but let himself socially locked among them and neglects his own friend circles which feeds his resentment against Rachel.
- Delayed Narrator Introduction: The narrator at first seems to be a standard third-person omniscient narrator, only to be revealed as the voice of Toby's friend Libby late in the first episode.
- Desperately Craves Affection: Rachel has massive abandonment issues which explains a lot in the unraveling of her marriage. As pointed by the narrator, Hannah does too.
- Desperately Looking for a Purpose in Life: Libby suffers from this. She quit her job as a man magazine's writer when she realized that she would never break the glass ceiling. She ended up as a stay-at-home mom, frustrated by the lack of excitment of her suburbian life and stucked in her attempts to realize herself.
- Familiar Soundtrack, Foreign Lyrics: In the final episode, a Hebrew cover of Rachel Platten's "Fight Song" plays after Toby's daughter Hannah decides she doesn't want a bat mitzvah.
- Formerly Fat: as alluded by his mother, Toby used to be chubby. This explains why he adhere to a strict healthy diet, to the annoyance of Rachel.
- Family Versus Career: the dilemma of Rachel. She thought she wanted a family (as seen in a flashback where she express to Toby her desire for a close-knit family like his) but realized after her first pregnancy that she is much more fulfilled by her successful career and is not much of a family woman. To an extent, this applies to Toby as well who must juggles his family when Rachel went awol and his career.
- Gypsy Curse: A Jewish variation. While on a Birthright-esque trip to Israel in college, Toby, Libby and Seth were alternatively blessed and cursed by a beggar woman. They amuse themselves years later by concocting similar curses for each other, which they realize probably don't really mean anything.
- Happily Married: Libby on the surface. She has a great husband, two beautiful kids she loves and a nice life in suburbian New Jersey. Both newly-divorced Toby and aging playboy Seth envy her for that. However she feels that she needs more, putting strain on her family life. See Desperately Looking for a Purpose in Life.
- Henpecked Husband: Toby has a complicated relationship to this trope. From his perspective, he was forced into this kind of marriage by his far more successful wife, even though with his doctor’s salary he would be considered rich and capable of being the primary breadwinner just about anywhere other than their wealthy neighborhood in Manhattan. This is pointed by his divorce lawyer when she informs him that in the story of their divorce he is 'the wife' in regards of finance and child care.
- It's All About Me: Toby acts like this a lot, including flipping out over Rachel’s boss having once hit on her in the middle of a much more serious story about her getting denied a promotion due to her pregnancy. He also displays a massive lack of empathy when Libby informed him that Rachel's disappearance is due to a severe mental breakdown. Libby calls him out on this.
- Missing Mom: Rachel's mother died when she was young, triggering abandonment issues in Rachel.
- No Celebrities Were Harmed:
- Rachel’s star playwright-actress discovery, Alejandra Lopez, is basically a female and more working-class Lin-Manuel Miranda, producing a rap-influenced show about American history ("Presidentrix") as a riff on Hamilton.
- Libby’s one-time journalist idol Archer Sylvan is mostly a fictionalized Hunter S. Thompson, with maybe a dash of Tom Wolfe mixed in - boasting a rambling genius, nigh-unlimited expense accounts, and rather outdated attitudes towards women
- Sanity Slippage: the reason of Rachel's disappearance. She went to a yoga-wellness weekend retreat with her lover. Work disconnection and being dumped triggered a Sanity Slippage.
- Shout-Out: A copy of Portnoy's Complaint is displayed prominently on Toby's bookshelf. Roth's novel is also about a smart neurotic Jewish man with overriding sexual obsessions.
- Switching P.O.V.: The first six episodes are from Toby's P.O.V and narrated by her friend Libby. However once Libby found Rachel, the P.O.V. switches to Rachel in the seventh episode and then Libby in the last one.
- Unreliable Narrator: the narrator is Libby. As a close of friend of Toby, she tells the story from his point of view and his biases and projects her own issues on the story. In the seventh episode after she found Rachel who explains her her story, she realizes that she only told one part of the whole story.
