Reel Estate

Getting the NYC real estate right in Hulu’s ‘Fleishman is in Trouble’ is critical to this tale of former spouses in crisis

  • The new eight-episode series is a tale of two Upper East Sides
By Kelly Kreth  |
November 22, 2022 - 2:30PM

Toby Fleishman, played by Jesse Eisenberg, with Meara Mahoney Gross, and Maxim Swinton.

Linda Kallerus/FX

“Fleishman is in Trouble,” an eight-episode drama that debuted on Hulu last week, is a story about a recently divorced doctor, Toby Fleishman (Jesse Eisenberg), coping with being newly single in New York City while juggling work and raising two kids. But this is no typical break up: Toby’s ex-wife Rachel (Claire Danes) mysteriously disappears at the start of the show and the quirky show quickly morphs from a “Sex and the City” vibe to a Gen X version of “Search Party.”  

Based on her book of the same name, Taffy Brodesser-Akner created and executive produced the series, which takes place in 2016 and is set mostly on the Upper East Side. Lest you forget what was happening then: There are “Hillary for President” signs everywhere in liberal Yorkville.  

[Editor's note: When a movie or TV show is set in New York City—and if the people making it are savvy—real estate becomes part of the story itself. In Reel Estate, Brick Underground reality checks the NYC real estate depicted on screen.]

The first two episodes focus on the disparities between Toby and Rachel, which are mirrored by the two distinct Upper East Sides—the tony one west of Lexington and the less elite one to the east. The contrasts of the rich and even richer are highlighted through their real estate—more on that in a moment.  

Getting the NYC real estate right

All the characters are typical wealthy New Yorkers, and the real estate seems familiar and realistic as well. “I have this thing where if I'm told I'm watching something that takes place in New York, if I can't reconcile the locations in my head, it just becomes too much work for me to wonder what they're trying to convey,” Brodesser-Akner said recently in Town & Country.  As such, real NYC locations include the 92nd Street Y—where Lululemon clad moms complete with chiseled arms and wearing sassy-sloganed tees congregate—and Madame Bonte, a café located at 1834 2nd Ave., where Toby meets with his childhood friends, Seth and Libby. There are also scenes in the Corner Bookstore, and Temple Shaaray Tefila and a quick shout-out to Dorrian’s.  

“The triumph was shooting inside a New York City bus. That’s the hard location to get,” Brodesser-Akner said.

A divorced dad’s pad

A quality series doesn’t just tell, it shows. We learn a lot about the characters by seeing where they live. Toby’s new apartment is a very basic two bedroom in an older post-war building. While it has an elevator and basic lobby, it is anything but luxe. It is reminiscent of every generic elevator building in the area, right down to the mezuzah outside Toby’s apartment door. Stark, bland hallways, generic furnishings and even the obligatory bean bag chair are almost depressing.

Toby’s young daughter balks at the thought of her rich grammar school friend finding out where her dad now lives. She also balks at having to ride the bus a few blocks home from the Y instead of hopping in a cab like all her friends do. 

‘A prisoner of the Upper East Side’

Toby knows his new place is a hovel compared to the palace—the family apartment he just moved out of. His friend jokes it reminds him of their dorm room in Israel. Toby kvetches he has to live there because he is a “prisoner of the Upper East Side.” He’s a hepatologist at a top UES hospital and must be able to get to and from work quickly, especially now that he shares custody of his two young kids who go to school in the neighborhood.

And besides, Toby, a do-gooder more concerned with helping others than material things, quips that he hated the high ceilings in his former home anyway. “They made the doormen dress like they are in the military” there, he says.  

Mismatched real estate types

The contrast with his ex’s place, from which he was banished during the split, is like night and day—and underscored by the name of her high-rise, The Golden. In a flashback we see how disconnected the married couple truly was. Toby is content to rent a smallish apartment in a nondescript building, while Rachel, a top exec in the theater world, yearns to buy a place of their own. She feels they need more space and that if they buy, they will put down roots and live there a hundred years. (Spoiler: Expensive real estate does not prevent divorce.) 

To push this agenda, while visiting their uber rich friends in their second home (of four!) in Saratoga, Rachel convinces their friend to offer Toby a high-level pharma job, which would likely triple his $300,000 hospital salary.

Toby protests; he feels there is no need to earn that much working for a soulless pharma company. He points out that outside NYC his income would be considered rich, but in NYC it is embarrassingly low. Still, he is content with slogging along in the hospital because he is helping people. Fancy real estate be damned!

Pushed into buying a luxury apartment

Even after he turns down the high-paying job offer, Rachel takes him to see a unit in a new luxury development being developed by that same friend (The Golden). She tells Toby they have the option to put in a bid before it is on the market. Defeated, Toby agrees.  

It’s total luxury: Floor-to-ceiling windows, gilded everything, and fresh flowers in the lobby, with a garage to house Rachel’s beamer. It is glitzy and glamorous. One can almost hear harp music playing upon entering as if being beckoned by angels to heaven.  

Toby is dejected. This type of luxury real estate is everything he hates about NYC: “New money imitating old money.”  

But don’t feel too bad for Toby. He has a second home of his own—in the tony Hamptons. He certainly isn’t advocating for living in a walk-up tenement or roughing it in any way. This is not a story about the rich and the poor—and the lines between good and bad are equally muddied. He is not nice at all to his kids’ nanny and fires her without a thought after discovering his young son searched a porn website on her watch. He complains when the air conditioner in his new place isn’t cool enough and quickly decides to drive east to be more comfortable. Even a man of the people has his limits!  

When Rachel fails to pick up the kids one day, Toby has to scramble. He takes the children to the hospital where he works and has them sit in the conference room while he makes rounds. Eventually asks for two days off and drives the kids to hole up in their Hamptons home.

His plan backfires when the woman his wife hired to look after the house calls the police. They arrive to find Toby swimming naked in the pool and ask him to leave because he is no longer the rightful owner of the home. It seems he lost a lot more than just his pants in that divorce.

Back home in the less-than-glitzy part of the city, Toby heads to the grocery store, where he is confronted with a $14 watermelon. As if that isn't shocking enough, that’s where he learns from his wife’s friends that she’s been spotted sleeping in the park. It seems she’s had a breakdown, or maybe it is a breakthrough. 

Rachel’s own story is shocking and twisty—and we don’t want to give too many spoilers away. Suffice it to say that sometimes you have to find your own way home, even if it’s not where you wanted or expected to end up.



Kelly Kreth

Contributing writer

Contributing writer Kelly Kreth has been a freelance journalist, essayist, and columnist for more than two decades. Her real estate articles have appeared in The Real Deal, Luxury Listings, Our Town, and amNewYork. A long-time New York City renter who loves a good deal, Kreth currently lives in a coveted rent-stabilized apartment in a luxury building on the Upper East Side.

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