‘Fleishman Is in Trouble’ Nails Middle-Age Malaise in the Tinder Age

The funniest thing about the mini-series drama Fleishman Is in Trouble is how it tacitly reinforces a delusion common among American men in their late 30s and early 40s. Namely, had Tinder been invented ten years earlier, they would have spent the salad days of their adulthood having more sex. Soon after his marriage ends, Toby Fleishman (Jesse Eisenberg), a 41-year-old doctor who is not the spitting image of Brad Pitt, creates a profile on what the series refers to as “the apps”. Almost immediately, he starts receiving solicitations from a bevy of attractive New York women, all willing to bend over backward (sometimes quite literally) to get Dr. Fleishman in bed. Not since Seinfeld‘s George Constanza has a less handsome denizen of one of New York’s upper sides enjoyed such a successful and inexplicable run of success in the sack.  

To say this scenario strains credulity would be an understatement. Tinder and other hookup apps may facilitate sexual congress between interested parties, but the notion that the simple act of creating a profile can turn a physically unimpressive, middle-aged man into an irresistible object of desire is laughable—and not unlike the misguided fantasy Xennial dudes cling to when they imagine a life in which their 20s coincided with the early stages of the smartphone revolution. 

Yet Fleishman Is in Trouble portrays Toby’s app-fueled sexual prowess with a winning mix of the wide-eyed wonder Toby feels while receiving hand jobs in alleyways from women he’s just met, and with zippy energy that, as a viewer, you feel more inclined to laugh out loud then roll your eyes. At least I did. Most films and television shows about white and relatively well-heeled New Yorkers, from Woody Allen films to sitcoms like Friends and How I Met Your Mother, involve certain degrees of fantasy. Their portrayal of a world where the dinner party conversations are a smidge too clever and the apartments a tad bigger than they should be is central to their appeal. In Fleishman Is in Trouble, set in Manhattan’s upper east side in the summer of 2016, the ease with which Toby finds sex online is a little too effortless.

The enjoyment Toby and his online paramours derive from these hookups run counter to the middle-aged disaffection that saturates so much of Fleishman Is in Trouble. The first six episodes focus on Toby’s efforts to navigate a life that does not include Rachel (Claire Danes)—the woman to whom he was married for more than a decade and who has dropped their two kids off at Toby’s apartment a day earlier than expected – and disappeared. 

Toby fumes and fusses, more annoyed than incensed by what he perceives as Rachel’s callous indifference to their children, their custody arrangement, and his responsibilities as a patient-centric hepatologist at a local hospital. At work, he endures professional humiliation that is partially the result of the many work days he misses to care for his children. He grouses to Libby (Lizzy Caplan) and Seth (Adam Brody), two friends from college with whom he’s reconnected, about the travails of his life and his irresponsible ex-wife. He visits and revisits New York’s Natural History Museum alone and with his children and spends a perplexing amount of time contemplating an exhibit about Vantablack, the darkest man-made material.

Throughout these episodes, both Toby and the voiceover narration (provided by Libby, a former journalist turned unfulfilled housewife) treat Rachel as the villain. The founder and chief executive of a successful theater talent agency, Rachel’s monomaniacal focus on her career caused fissures in her and Toby’s relationship. Her lack of respect for Toby is why she felt empowered to pawn their kids off on him so that she could vanish without a trace or an explanation. At least, this is the story Toby and Libby are content to tell. 

It’s not until Fleishman Is in Trouble‘s seventh and penultimate episode that the viewer is treated to Rachel’s side of the story. “Me-Time” is a gut punch transmuted into 60 minutes of television. The viewer watches as Rachel, an orphaned child raised by a less-than-loving grandmother, uses ambition and talent to achieve remarkable career success only to be labeled by her husband as a money-obsessed girl boss. We watch a smug ob-gyn perform an invasive medical procedure without her consent, turning the birth of her first child into a lasting trauma. We watch as the pressures of balancing a high-caliber career and motherhood rob Rachel of any joy she once derived from life, only for her husband to treat her as an adversary rather than work harder to appreciate her perspective. 

Indeed, the “Me-Time” episode is the pinnacle of the series. It flips the narrative on its head by refocusing the story on Rachel’s genuine tribulations rather than Toby’s not-so-serious trials, and it takes full advantage of Danes’ remarkable talents as an actor. Danes does her most memorable work in television, and everything she does onscreen during “Me-Time”—from engaging in primal scream therapy to chomping on a leaf of lettuce as if she were trying to bite off the head of a small bird to holding a bagel between her legs while lost in a haze of malaise—is absolutely perfect. She doesn’t chew up the scenery so much as render it less relevant because nothing can compare to or compete with her onscreen presence. 

Unfortunately, Fleishman Is in Trouble‘s eighth and final episode, “The Liver”, can’t match the explosive power of “Me-Time”. It ties up the story’s loose ends—Libby makes peace with her life as a suburban mom and decides to write a book; Seth gets engaged—in a mix of maudlin emotions and even hints at the possibility that Toby and Rachel will reconnect and fix their broken relationship (a twist that’s not entirely believable). However, “The Liver” lacks the outright hilarity of Toby’s online “dating” shenanigans and the raw power of watching Danes show the audience Rachel’s side of the story.  

Based on Taffy Brodesser-Akner’s 2019 novel Fleishman Is In Trouble doesn’t have many positive things to say about marriage. All the couples here are either faking affection toward one another or outwardly miserable. The show is just as ungenerous when it comes to adult friendships. The Manhattan moms with whom Rachel works so hard to be pals are uninterested in connecting with Rachel (or one another) beyond sharing a routine of similar activities: picking kids up from tony daycares, attending yoga classes together, making small talk at dinner parties. Toby, Libby, and Seth’s decision to rekindle their college friendships in middle age looks sweet, but the three spend most of their time together passive-aggressively sniping at one another. While each character experiences certain levels of career success, none seem to derive the lasting satisfaction often associated with a fruitful professional life. 

As a work of television, Fleishman is in Trouble is both literate and full of wonderful performances. The dialogue and voiceover narration crackles with the wit and spunky rhythm of Brodesser-Akner’s prose. While no one can quite match Danes in terms of the command she brings to the screen, Caplan perfectly conveys Libby’s blunted verve and regret over paths not taken that are central to her character. As Toby, Eisenberg tucks a welcome layer of vulnerability underneath the nervy nebbish persona he’s pulled off for years in films like David Fincher’s The Social Network (2010) and Ruben Fleischer’s Zombieland (2009) Brody uses his turn as Seth to confirm his stature as a B-list George Clooney—an actor dripping with easygoing charm who pulls off wearing skinny sweatpants and slim-feet tees with aplomb. 

The only time we see characters in the throes of something resembling unabashed joy in Fleishman Is in Trouble is found in the moments when Toby and his app buddies are having a go at it in bed. Middle age is inherently bleak in the world of Rachel, Dr. Fleishman, and Libby, and there’s no easy cure for the early-40s blues. Toby staves off malaise by cutting loose. Whether he, his ex-wife, and his friends can find a more lasting cure to the melancholy that plagues them is a question the series doesn’t answer.