On Fleishman Is in Trouble and the Sex and the City Problem

Reese, the charismatic trans femme star of Torrey Peters’s 2021 novel Detransition, Baby, has a theory. When a woman enters her 30s and the shine of her youth starts to dull, she runs into the Sex and the City Problem: a constrained set of life paths charted by heterosexual culture (and the popular show from the 00s). In Detransition, Baby, Reese believes these four limited options for finding meaning—a career, a partner, a baby, or a life dedicated to art—are finally available for trans women like her, but she’s not sure that’s enough. She wants a baby, and finds common ground with her detransitioned ex, and the divorced cis woman who’s carrying his child, both of whom are trying to imagine their own roles beyond the four permutations.

As a messy threesome, they explain and argue their way towards a new script; they don’t solve the SATC Problem, they transcend it. The connection between gender transition and divorce in the book is no accident. Torrey Peters even dedicates the novel to divorced cis women, who, like her and other trans women, are finding a new path for themselves outside of HBO’s four existential horsewomen.

The characters in Fleishman Is in Trouble are far from the divorced women in the Petersian mold. A decade into their own SATC selections, they’ve encountered the sharp edges of the boxes they’ve chosen: a crushing high-powered career for Rachel, a dulling suburban mom life for Libby, and even a gilded cage for side character Nahid, who literally can’t leave her apartment. They toss and twist to great emotional effect, but in the end Rachel and Libby return to their roles without stretching towards a more complicated, pleasurable—and less well-cataloged—life.

Neither of these women attempt to be truly alone, neither explores what would happen if she asked for something new from her partner. Fleishman offers a moving dramatization of the dangers of the SATC Problem for women of a certain age and class. But without any serious investigation of what’s on the other side of those options, Brodesser-Akner limits the power of Fleishman to the narrow stories we’ve already been fed; Like Sex and the City itself, Fleishman Is In Trouble is ultimately a conservative tale.

In Fleishman, Rachel has a clear and glittering vision for her future. Having grown up without money or close family, Rachel takes aim toward the life she always wanted as a child, which at first seems to her like marrying Toby Fleishman, a doctor with a large and loving family, and finding the next rising playwright for her boss to represent.

But as often happens on the slippery slope of mimetic desire, “great” starts to mean “perfect,” and Rachel finds herself attempting to juggle a full house of SATC characters. She heads her own successful agency, pays for top tier private schools while showing up for the required mom functions, and moves the Fleishmans into two coveted and pricey zip codes—all the back-breaking “accomplishments” of privilege chronicled in the recent internet-breaking piece on the Fleishman Effect for The Cut—and yet she remains miserable. Rachel’s balancing act ends as it always does: in disaster.

As an audience, we don’t meet Rachel until we’ve seen the effect of her crash on Toby and their kids. They are struggling and devastated when she goes MIA, presumably on an extended yoga retreat to have some “me” time. Toby grows furious, blaming Rachel’s greed and heartlessness for their pain. And we do too, as Rachel’s children cry in her absence. Why did she have children if she couldn’t handle it?  She chose wrong, we think. She should’ve stuck to being a Samantha.

But in later chapters and episodes, Brodesser-Akner reveals that Rachel hasn’t left her family exactly; she’s left the entire plane of reality. After separating from Toby and getting dumped by her rebound DILF, Rachel spirals into a psychological breakdown that leaves her trundling through Manhattan in pajamas, ordering the same takeout lo mein over and over, only to discover yet again that she hates the taste of her own decisions.

Brodesser-Akner sweeps us back through Rachel’s history, to a gut-wrenching episode of postpartum depression that she mostly had to brave on her own, through countless conflicts with Toby over the minutiae of their life instead of discussions about its very shape. Through precise writing and stellar performances—including an updated version of the showstopping sobs that Claire Danes has built her career on—we can feel the agony of a life that turns out to be much less than expected. It was the box that broke Rachel, the limits and demands of living up to a caricature of happiness without asking if she was actually happy.

The audience gets to have this realization about Rachel, and it feels both heartbreaking and hopeful; if she can do things differently, maybe she’ll find a new way forward. But Rachel doesn’t get the same revelation for herself. Instead, the story leaves her in bed, trying to sleep off all her wrong choices. It’s Libby who tucks her in. It’s Libby who tells us that Rachel returns to Toby when the summer heat breaks. Rachel just disappears.

Libby, a classic pick-me girl since college, is the narrator of Fleishman Is in Trouble, a bewildered newly not-working mom in the suburbs who wonders how she ended up in such a well-maintained version of hell. She was a Carrie, a writer who longed to squeeze the bloody heart of adventure onto the page, but she ended up on the publishing sidelines before making a right turn into the life of a Charlotte. Libby leaps at the chance to revisit her youth vicariously through Toby’s new single life and their friend Seth’s enduring one.

Like Rachel, she leaves her family behind—in New Jersey this time, for a taste of life before the SATC Problem came into view. Libby is trying on the fantasy of returning to the beforetimes, and young Libby believed all men. She buys her friend Toby’s version of his divorce; she sees Rachel as “an ambition monster,” as he calls her. But when Libby runs into a reduced and mumbling version of Rachel in the park, and hears about the all-too-familiar conditions that brought her there—the loneliness of motherhood, the pressure of class-mandated achievement, the judgment of unequal partnership—she begins to see the parallels in their lives and the limits of both of their options.

Libby goes to Toby to advocate for Rachel but when he refuses to change the narrative he’s constructed, she does not push back. Instead, she is shocked into reconsidering her minor rebellion. She grows grateful for the safety of the choices she’s already made. “Maybe it’s like what they say about democracy,” Libby says to Seth about marriage, unconvincingly. It’s the worst, but it’s better than any of the other options. However, the other options—divorce, sure, but also asking more of the institution itself—remain uninterrogated and largely hypothetical for the women of Fleishman.

Like Rachel, Libby returns to her family. She curls into bed with her husband and tells him how much she loves him, as if there were nothing more to say or expect. Libby can’t imagine a world outside the simple math of the SATC Problem. Because the entire story is in her voice, we can’t either. Rachel and Libby are trapped in the limiting beliefs of the upper crust of the NYC-metro area, where stressed-out moms hire Soviet math tutors to give their kids an advantage one step beyond their own. With that kind of wealth, education, and opportunity, if Rachel and Libby can’t break free, who can? It’s important to remember, though, that Fleishman Is In Trouble is fiction.

Libby tells her friends that she might try writing a novel; she imagines the fix is to become a Carrie again. Maybe that will help. But Libby does not even consider that she might find joy within the messiness of something altogether different. She cannot fathom that the one simple trick for success is totally free: imagining a unique and pleasurable life with the people you love. In Detransition, Baby, the time and care the characters take to tell each other their theories and plan new futures together are just as important as their final choices.

In fact, the novel ends without revealing if the threesome decide to become a family. Their struggle to reinvent is the point of the book. In Fleishman, Libby could search for freedom in real conversations with her husband or in time with her children that feels pleasurable to her and not her neighbors. She could explore how to make her days too wild and messy to be captured in an hour-long prestige show. Instead, Libby slides silently into her old side of the bed.

The moral of Fleishman is that “this is as young as you’ll ever be,” as Libby intones over and over to us and to herself in the show’s final episode. There is no possible return to the moment before the SATC Problem, the time before we all made the choices we did. This is true, and a good thing to remember in the throes of any mid-life crisis. But what is also true and what none of the characters in Fleishman engage with is that youth and class conformity have little to do with happiness. We can make infinite choices if we push back against the pressures of the boxes we’ve built around us. Libby and Rachel can choose again and again forever. And I can’t help but wonder if that would have made a more novel story.